The 95 Best Comedy Movies Ever – /Film

The 95 Best Comedy Movies Ever – /Film

How does one even approach making a list of the best comedies? Of all genres, this is the one that’s the most difficult to pin down. First of all, comedy is entirely subjective — everyone’s sense of humor is different. What works for one person will fall completely flat for another. Then, how do we account for comedy that has aged poorly, but has had a huge impact on the genre, influencing cinema for decades after its release?
Really, embarking on this whole undertaking is like opening up a can of worms. Nevertheless, we’ve resolved to give it a try. Consider this list a primer of the best comedies released over the course of cinematic history — with any luck, you’ll find more than a few laughs in the films listed here!

If anything, “9 to 5” has only grown more relevant in the years since its release. Who can’t relate to the feelings of rage and powerlessness that one experiences when dealing with a particularly monstrous boss at work? 
In “9 to 5,” three secretaries have had enough with their infuriatingly misogynistic boss, and they hash out a revenge scheme with hilarious consequences. Aside from Dolly Parton’s iconic opening theme, each of the film’s three leading ladies are given an opportunity to shine. Tara Brady of the Irish Times says that the film, “retains a barbed relevance beneath its capering and unflattering hairstyles, not to mention one of cinema’s most badass trios.”
Starring: Jane Fonda, Lily Tomlin, Dolly Parton
Director: Colin Higgins
Year: 1980
Runtime: 110 minutes
Rating: PG
Rotten Tomatoes Score: 83%

One of the rare sequels that vastly surpasses the original, “Addams Family Values” is a delicious ode to the macabre. When a serial husband killer named Debbie (Joan Cusack) gets her hooks in the hapless Uncle Fester (Christopher Lloyd), the Addams children immediately see through her and are subjected to the worst possible torture as a result: summer camp. Wickedly funny throughout, “Addams Family Values” owes its classic status to Cusack’s performance as the melodramatic, self-involved antagonist — her villain monologue, which comes complete with a slide show presentation, is one for the ages.
Starring: Raul Julia, Anjelica Huston, Christopher Lloyd
Director: Barry Sonnenfeld
Year: 1993
Runtime: 93 minutes
Rating: PG-13
Rotten Tomatoes Score: 77%

With an all-star cast that includes Monty Python alums John Cleese and Michael Palin, Kevin Kline, and Jamie Lee Curtis, “A Fish Called Wanda” was one of the premier comedy events of the 1980s. When a group of misfit criminals embarks on a carefully planned diamond heist, everyone just can’t stop double-crossing one another. “A Fish Called Wanda” has some of the best comedic dialogue of the era, earning itself an Oscar nomination for best writing and best director, as well as a win for Kevin Kline for best actor.
Starring: Jamie Lee Curtis, Kevin Kline, John Cleese
Director: Charles Crichton
Year: 1988
Runtime: 107 minutes
Rating: R
Rotten Tomatoes Score: 96%

Back when the relationship between Will Ferrell and Adam McKay was firing on all cylinders, “Anchorman: The Legend of Ron Burgundy” gave birth to dozens of instantly quotable lines. Ron Burgundy (Ferrell) is the unquestioned king of 1970s San Diego news, but his supremacy is challenged when the network brings in a female co-anchor (Christina Applegate). Their rivalry leads to a hilarious fall from grace for Burgundy, as well as a wacky romance between the two leads. But Burgundy would be nothing without his news team, which is comprised of David Koechner, Paul Rudd, and Steve Carrell, all of whom make their mark on the film in endlessly entertaining ways.
Starring: Will Ferrell, Christina Applegate, Paul Rudd
Director: Adam McKay
Year: 2004
Runtime: 95 minutes
Rating: PG-13
Rotten Tomatoes Score: 66%

The gender politics of “Animal House” may not have aged particularly well (and neither have the frat’s hazing rituals), but its influence on raucous R-rated comedies is too significant to ignore. A pair of freshmen pledge Delta Tau Chi after being rejected by the more prestigious fraternities on campus. There, they find there a community of misfits singularly committed to the college party lifestyle, led by the laidback Eric (Tim Matheson) and the iconic Bluto, played by John Belushi at the height of his fame. Over-the-top and full of raunchy humor, “Animal House” would serve as the definitive college sex comedy for generations.
Starring: John Belushi, Tom Hulce, Tim Matheson
Director: John Landis
Year: 1978
Runtime: 109 minutes
Rating: R
Rotten Tomatoes Score: 90%

Although Cary Grant was primarily known for his romantic comedies throughout the ’30s and ’40s, romance takes a backseat in the pitch black “Arsenic and Old Lace.” Just before he departs on his honeymoon, Mortimer Brewster (Grant) pays a visit to his kindly aunts, only to learn that they have been cheerfully murdering people and burying them under their floorboards. As a much-put-upon nephew whose aunts just don’t seem to grasp the enormity of their actions, Grant plays one of the most legitimately hilarious straight men in comedy history.
Starring: Cary Grant, Priscilla Lane, Peter Lorre
Director: Frank Capra
Year: 1944
Runtime: 118 minutes
Rating: NR
Rotten Tomatoes Score: 83%

A delightful parody of 1960s spy films, “Austin Powers: International Man of Mystery” packs more gags into a minute than most movies manage over their entire run time. Mike Myers stars as Austin Powers, a shagadelic English spy from the swinging ’60s who is cryogenically frozen and unthawed in the ’90s to battle his greatest enemy, Dr. Evil (also played by Myers). But Powers doesn’t just have to face off against Dr. Evil: He has to learn the ways of an entire new world, one with very different sexual politics than the era he left. With a cheeky grin, Mike Myers puts all of his considerable comedic talents into the dual roles.
Starring: Mike Myers, Elizabeth Hurley, Michael York
Director: Jay Roach
Year: 1997
Runtime: 89 minutes
Rating: PG-13
Rotten Tomatoes Score: 73%

Released in the thick of the pandemic, “Barb and Star Go to Vista Del Mar” as a balm for the weary soul. Kristen Wiig and Annie Mumolo play a pair of Midwestern best friends who go on vacation to Florida, leaving their small hometown for the first time ever. Unfortunately, things don’t go exactly as planned — as soon as they arrive at the Vista Del Mar resort, the two quickly become embroiled in a villainous plot to release a horde of lethal mosquitos. Aside from the two delightful lead performances, the film features a hilarious turn from Jamie Dornan, who is given a rare opportunity to display his surprising comedic prowess.
Starring: Kristen Wiig, Annie Mumolo, Jamie Dornan
Director: Josh Greenbaum
Year: 2021
Runtime: 106 minutes
Rating: PG-13
Rotten Tomatoes Score: 80%

There aren’t many films that straddle the line between horror and comedy as well as “Beetlejuice.” When a young, strait-laced couple (Geena Davis and Alec Baldwin) die in a car crash, a new family moves into their home. The only problem? The recently deceased homeowners are still occupying it, and are horrified by the changes made by the cosmopolitan Deetzes, who are played by Catherine O’Hara and Jeffrey Jones. That’s where Beetlejuice (Michael Keaton), a demonic figure guaranteed to scare away the humans, comes in. Keaton delivers a frenetic performance in the titular role, and a young Winona Ryder steals the show as the deeply morbid Deetz daughter, Lydia.
Starring: Michael Keaton, Winona Ryder, Geena Davis
Director: Tim Burton
Year: 1988
Runtime: 92 minutes
Rating: PG
Rotten Tomatoes Score: 85%

A dynamite collaboration between director Hal Ashby and actor Peter Sellers, “Being There” satirizes both class and the world of politics. When a humble gardener (Sellers) is mistaken for an eccentric gentleman with courtly manners, he finds himself bemusedly hobnobbing with the country’s elite. “Being There” would earn an Oscar nomination for Sellers, as well as a win for his costar Melvyn Douglas. Richard Combs of Sight & Sound referred to the film as “one of the boldest of commercial comedies, for the way it turns on passages of dead time, the dreadful pauses while other characters struggle to see the significance in each of Chance’s cryptically meaningless remarks.”
Starring: Peter Sellers, Shirley MacLaine, Melvyn Douglas
Director: Hal Ashby
Year: 1979
Runtime: 130 minutes
Rating: PG
Rotten Tomatoes Score: 95%

By the time “Best in Show” came out in 2000, director Christopher Guest had long developed a reputation for being one of the leading voices in improvisational mockumentary comedy. Here, he brings together some of his most frequent collaborators to capture the epic highs and lows of the competitive dog show. Complete with overbearing pet owners and larger than life characters, “Best in Show” has a lovably chaotic energy that perfectly showcases the spirit of these well-intentioned oddballs.
Starring: Michael McKean, Catherine O’Hara, Eugene Levy
Director: Christopher Guest
Year: 2000
Runtime: 90 minutes
Rating: PG-13
Rotten Tomatoes Score: 93%

John Cusack was one of the go-to teen stars of the 1980s, but while many of his films were light-hearted romantic comedies, “Better Off Dead” taps into something much darker and more wickedly funny. Cusack stars as Lane Meyer, a high school student in a major depressive funk after his girlfriend dumps him for the captain of the ski team. As he copes, he befriends a French foreign exchange student who lives with his bizarre neighbors, drag races Korean immigrants who learned to speak English from watching Howard Cosell, and is chased by a very determined newspaper delivery boy. Filled with quirky, subversive humor, “Better Off Dead” has become a cult classic.
Starring: John Cusack, Diane Franklin, Curtis Armstrong
Director: Savage Steve Holland
Year: 1985
Runtime: 98 minutes
Rating: PG
Rotten Tomatoes Score: 77%

Most kids are impatient to grow up. Few are actually able to will themselves into becoming an adult overnight with the help of a mysterious Zoltar machine. But that’s exactly what Josh Baskins (Tom Hanks) does in “Big.” Suddenly forced into the world of adults while still having the mind of an adolescent, Josh is bereft — until he lands a great job working at a toy company and starts dating his coworker, that is. Set aside the weirdness of this poor woman coming to terms with the fact that she’s inadvertently fallen in love with a child, and you’ve got a charming comedy with a winning performance from Tom Hanks.
Starring: Tom Hanks, Elizabeth Perkins, John Heard
Director: Penny Marshall
Year: 1988
Runtime: 104 minutes
Rating: PG
Rotten Tomatoes Score: 97%

There’s really no such thing as a bad Mel Brooks movie, but “Blazing Saddles” stands among his very best. Starring Cleavon Little as Bart, the first Black sheriff in the dusty western town of Rock Ridge, the parody skewers the Western genre and its inherent racism as Bart and his cowboy friend (Gene Wilder) team up to protect the town from local criminals. Roger Ebert called the film a “crazed grabbag of a movie that does everything to keep us laughing except hit us over the head with a rubber chicken.”
Starring: Gene Wilder, Madeline Kahn, Cleavon Little
Director: Mel Brooks
Year: 1974
Runtime: 93 minutes
Rating: R
Rotten Tomatoes Score: 89%

An ode to high school overachievers everywhere, “Booksmart” stars Kaitlyn Dever and Beanie Feldstein as two graduating seniors who are horrified to realize that they’ve followed the rules their entire academic lives, never once letting loose to have fun. So, they resolve to make their final night before graduation count by hitting up some last-minute ragers, but their adventures hit quite a few speed bumps. From the girls’ awkward attempts to flirt to their drug-induced transformation into dolls, “Booksmart” gives its teen heroines the opportunity to be strange, codependent, and neurotic in a way that few films do.
Starring: Kaitlyn Dever, Beanie Feldstein, Skylar Gisondo
Director: Olivia Wilde
Year: 2019
Runtime: 102 minutes
Rating: R
Rotten Tomatoes Score: 96%

When it comes to cinematic comedy duos, few have as much chemistry as former “Saturday Night Live” co-stars Kristin Wiig and Maya Rudolph. In “Bridesmaids,” Wiig stars as Annie, a woman who feels threatened by the idea that her best friend Lillian is pulling away from her, especially as Lillian embraces a more grown-up life and prepares for her wedding. Believing that the seemingly perfect Helen (Rose Byrne) is taking her place, Annie acts out in ways that have wildly hilarious consequences. 
In addition to the charming lead performances, “Bridesmaids” proved that a comedy film starring an ensemble of women could not only be genuinely funny, but successful at the box office. It even garnered two Oscar nominations, including one for supporting actress for Melissa McCarthy.
Starring: Kristin Wiig, Maya Rudolph, Rose Byrne
Director: Paul Feig
Year: 2011
Runtime: 125 minutes
Rating: R
Rotten Tomatoes Score: 90%

The on-screen collaboration of Cary Grant and Katharine Hepburn is one of the best that classic Hollywood has to offer, and “Bringing Up Baby” shows why. Grant plays an exasperated paleontologist who is searching for the last bone to complete the skeleton of his beloved dinosaur. Hepburn is a kooky socialite with a pet leopard in tow, and a delightful little dog who has inconveniently buried said bone. Hijinks ensue. “Bringing Up Baby” was not a major financial success at the time, but it has since gone on to serve as the quintessential screwball comedy.
Starring: Cary Grant, Katharine Hepburn, Charles Ruggles
Director: Howard Hawks
Year: 1938
Runtime: 102 minutes
Rating: NR
Rotten Tomatoes Score: 94%

With some of the biggest comedy stars of the late 1970s signing on for “Caddyshack,” it was pretty much guaranteed to become a classic. The film follows the goings-on at a local country club, where teens and college students work as caddies for entitled golfers. “Caddyshack” lives and dies on the performances of its stars, especially Bill Murray as a groundskeeper locked in a battle with a rogue gopher and Rodney Dangerfield as a gregarious, loud-mouthed golfer. In the years since its release, it has become a comedy staple, and remains one of the most quotable films to come out of the 1980s.
Starring: Chevy Chase, Bill Murray, Rodney Dangerfield
Director: Harold Ramis
Year: 1980
Runtime: 98 minutes
Rating: R
Rotten Tomatoes Score: 73%

Films like “Clerks” and “Empire Records” owe a significant debt to “Car Wash,” which really got the ball rolling on the modern ensemble comedy about a bunch of hard-done-by employees just trying to get through the day. The film takes place at a car wash in Los Angeles, where workers try to navigate obnoxious customers and an overbearing boss. Perhaps worst of all, however, they also have to contend with the boss’ son, a well-intentioned but patronizing twenty-something who has just returned from college as a self-professed man of the people, but who is nonetheless happy to take on a managerial role. 
Starring: Richard Pryor, George Carlin, Franklin Ajaye
Director: Michael Schultz
Year: 1976
Runtime: 97 minutes
Rating: PG
Rotten Tomatoes Score: 89%

A pitch-black satire based on the classic novel by Joseph Heller, “Catch-22” exemplifies the inherent absurdities of warfare. It stars Alan Arkin as a World War II pilot whose efforts to get sent home are stymied by the titular catch-22: a discharge order would require evidence of mental instability, but the mere act of requesting a transfer away from death and constant warfare is, if anything, proof of sanity. Of Mike Nichol’s directorial efforts, Time said, “It is the book’s cold rage that he has nurtured. In the jokes that matter, the film is as hard as a diamond, cold to the touch and brilliant to the eye. To Nichols, “Catch-22″ is ‘about dying’; to Arkin, it is ‘about selfishness’; to audiences, it will be a memorable horror comedy of war, with the accent on horror.”
Starring: Alan Arkin, Martin Balsam, Bob Newhart
Director: Mike Nichols
Year: 1970
Runtime: 121 minutes
Rating: R
Rotten Tomatoes Score: 80%

When a trio of Manhattanites take a “relaxing” trip to a dude ranch in “City Slickers,” comedy ensues. A grizzled cowboy, Curly (Jack Palance), tries (and frequently fails) to teach the trio of well-meaning doofuses the ropes, and their ill-fated efforts put a comedic spin on concepts of traditional masculinity and vitality. While the entire cast turns in note-perfect performances, Palance’s memorable turn was singled out for acclaim, taking home the Academy Award for best supporting actor in a rare win for a comedy.
Starring: Billy Crystal, Daniel Stern, Bruno Kirby
Director: Ron Underwood
Year: 1991
Runtime: 112 minutes
Rating: PG-13
Rotten Tomatoes Score: 91%

An ultra-low budget independent film reportedly made for under $30,000, “Clerks” single-handedly put director Kevin Smith on the map. Its premise is simple: The film revolves around two underachieving store clerks, Dante and Randal, and the long conversations they have at work to avoid dealing with the customers that plague their days. A major box office success, “Clerks” launched the View Askewniverse (the name given to Smith’s films that take place in the same narrative universe) and introduced the now-famous characters of Jay and Silent Bob.
Starring: Brian O’Halloran, Jeff Anderson, Jason Mewes
Director: Kevin Smith
Year: 1994
Runtime: 91 minutes
Rating: R
Rotten Tomatoes Score: 90%

How many great comedies are adaptations of popular board games? Possibly just this one. Set in a spooky mansion in 1950s New England, “Clue” takes place over the course of one dinner party with an extremely high body count. The murders begin to pile up, as the hapless guests desperately try to figure out who is responsible and keep themselves alive. “Clue” features kooky, fast-paced dialogue and a troupe of talented comedic actors who demonstrate an unshakeable commitment to playing it straight.
Starring: Tim Curry, Michael McKean, Madeline Kahn
Director: Jonathan Lynn
Year: 1985
Runtime: 96 minutes
Rating: PG
Rotten Tomatoes Score: 68%

A modern take on Jane Austen’s “Emma,” “Clueless” stars Alicia Silverstone as Cher Horowitz, an entitled Beverly Hills teen determined to play matchmaker for the people in her life, even though her schemes often get her into trouble. Cher’s most recent project is Tai (Brittany Murphy), a transfer student who she deems badly in need of a makeover. An icon of mid-1990s cinema, “Clueless” not only reflects the teen culture of the time, but successfully influenced it, with Cher’s very specific speech patterns and slang effortlessly becoming part of the zeitgeist.
Starring: Alicia Silverstone, Paul Rudd, Brittany Murphy
Director: Amy Heckerling
Year: 1995
Runtime: 97 minutes
Rating: PG-13
Rotten Tomatoes Score: 81%

By the late ’80s, there was no one bigger in the comedy world than Eddie Murphy, and “Coming to America” is one of his best films. He stars as Prince Akeem, who travels to America from the African nation of Zamunda in an attempt to escape an arranged marriage and ends up falling in love with a girl from Queens. Although it received mixed reviews when it was initially released (Sheila Benson of the Los Angeles Times referred to “Coming to America” as a “hollow and wearying Eddie Murphy fairy tale”), it was enormously successful at the box office, becoming one of the highest grossing films of the year.
Starring: Eddie Murphy, Arsenio Hall, John Amos
Director: John Landis
Year: 1988
Runtime: 116 minutes
Rating: R
Rotten Tomatoes Score: 73%

“Cooley High” is a coming-of-age story that serves as a counterpart to the more suburban nostalgia of George Lucas’ “American Graffiti.” It’s Chicago in the 1960s, and two best friends are attempting to navigate their senior year, with frequently humorous but sometimes tragic consequences. When it was released in 1975, “Cooley High” stood in sharp contrast to the blaxploitation films that were popular at the time, and it has long been considered hugely influential on directors such as Spike Lee and John Singleton.
Starring: Glynn Turman, Lawrence-Hilton Jacobs, Garrett Morris
Director: Michael Schultz
Year: 1975
Runtime: 107 minutes
Rating: PG
Rotten Tomatoes Score: 85%

As cynical as we can be about politics, deep down we often have an idealistic desire to believe that our leaders are honest people who could be forces for good if they were given the opportunity. In “Dave,” Kevin Kline plays a morally upright actor who bears a striking resemblance to the president — a similarity that comes in handy when the president suffers a debilitating stroke and urgently needs a stand-in. Dave takes advantage of his time in the White House to make a difference, and while there are a few comedic growing pains as he acclimates to the role, he quickly proves himself up to the challenge of running the nation. With warm, earnest performances from Kline and his co-star, Sigourney Weaver, “Dave” is an unbelievably likable production.
Starring: Kevin Kline, Sigourney Weaver, Frank Langella
Director: Ivan Reitman
Year: 1993
Runtime: 110 minutes
Rating: PG-13
Rotten Tomatoes Score: 95%

Perhaps one of the more divisive films on this list, “The Dead Don’t Die” is nonetheless a genuinely hilarious zombie comedy. It tackles all of the genre’s expected tropes, while also gleefully barreling into increasingly surreal territory as it entirely demolishes the fourth wall. 
In the film, a trio of small-town cops are caught unaware when zombies begin to attack, but things only get more dangerous and bizarre as the outbreak continues. With anarchic plot twists and disarmingly deadpan performances, “The Dead Don’t Die” isn’t quite like any other zombie comedy — whether that’s a good thing or a bad thing is open to interpretation.
Starring: Bill Murray, Tilda Swinton, Adam Driver
Director: Jim Jarmusch
Year: 2019
Runtime: 103 minutes
Rating: R
Rotten Tomatoes Score: 54%

All that Daniel (Matthew Macfadyen) wants to do is give his father a nice, respectable funeral, but it seems like the entire world is conspiring against him. Between his famous brother shirking his familial responsibilities, his cousin accidentally giving her strait-laced boyfriend (Alan Tudyk) heavy-duty hallucinogens, and his father’s secret lover (Peter Dinklage) turning up out of nowhere to demand hush money, Daniel has his hands full. A relentlessly funny comedy of errors, “Death at a Funeral” takes the concept of an emotionally restrained upper-class British funeral and turns it on its head.
Starring: Alan Tudyk, Peter Dinklage, Matthew Macfadyen
Director: Frank Oz
Year: 2007
Runtime: 90 minutes
Rating: R
Rotten Tomatoes Score: 62%

When Stalin dies in his sleep, his inner circle is less grief-stricken and more flummoxed. What are a group of yes men supposed to do when their leader isn’t around anymore, forcing them to grapple with one another for scraps of influence in the midst of a major power vacuum? 
With the television shows “Veep” and “The Thick of It” under his belt, director Armando Iannucci built his career around political satire, and “The Death of Stalin” should feel familiar to fans of his unique brand of comedy. With a strong ensemble of supporting actors who are each (unlike their characters) willing to share the spotlight, “The Death of Stalin” is side-splittingly hilarious.
Starring: Steve Buscemi, Jason Isaacs, Simon Russell Beale
Director: Armando Iannucci
Year: 2018
Runtime: 107 minutes
Rating: R
Rotten Tomatoes Score: 95%

From the king of surrealism himself, Luis Buñuel, “The Discreet Charm of the Bourgeoise” is a French comedy about a group of upper-middle-class friends who attempt to share a meal, despite a constant barrage of interruptions. Willing to play fast and loose with reality, the film is less one coherent storyline and more a series of intertwining vignettes. It was tremendously popular upon its release, earning an Academy Award for best foreign language film. Vincent Canby of the New York Times said of the film, “In addition to being extraordinarily funny and perfectly acted, ‘The Discreet Charm’ moves with the breathtaking speed and self-assurance that only a man of Buñuel’s experience can achieve without resorting to awkward ellipsis.”
Starring: Fernando Rey, Delphine Seyrig, Stéphane Audran
Director: Luis Buñuel
Year: 1972
Runtime: 100 minutes
Rating: PG
Rotten Tomatoes Score: 98%

The Wayans brothers have a long history with parody, beginning with “I’m Gonna Git You Sucka,” a 1988 film riffing on the blaxploitation genre. In “Don’t Be a Menace to South Central While Drinking Your Juice in the Hood,” they turn their comedic gaze to the Black coming-of-age films that came out in the early 1990s, including “Boyz N the Hood” and “Do the Right Thing.” When Ashtray (Shawn Wayans) moves in with his father, he learns all about life in the hood — in the funniest way possible. Although it was not particularly well-received by critics at the time, it has since become a cult classic.
Starring: Shawn Wayans, Marlon Wayans, Tracey Cherelle Jones
Director: Paris Barclay
Year: 1996
Runtime: 88 minutes
Rating: R
Rotten Tomatoes Score: 30%

In the aftermath of the Cuban Missile Crisis, audiences likely did not need a reminder of how close they were to nuclear war and destruction. Nevertheless, that’s exactly what “Dr. Strangelove” offers. It’s a chilling, subversive satire that skewers the American military and political structures as being full of buffoons, yes men, and dangerous megalomaniacs whose existence is the only thing standing between us and nuclear winter. It’s also a comedy. That’s the genius of “Dr. Strangelove” — it doesn’t pull its punches. It develops its characters with ludicrous absurdism that we can’t help but laugh at.
Starring: Peter Sellers, George C. Scott, Keenan Wynn
Director: Stanley Kubrick
Year: 1964
Runtime: 93 minutes
Rating: PG
Rotten Tomatoes Score: 98%

With “The Edge of Seventeen,” director Kelly Fremon Craig ushers in a new era of high school comedies in which teenage girls are allowed to be as weird and horny as their male counterparts. Hailee Steinfeld stars as an awkward student whose world is rocked when she learns that her best (and only) friend has been secretly dating her brother. To make matters worse, she accidentally sends her crush a graphic message on social media about all the raunchy things she’d like to do to him in the backroom of the pet store where he works. A perfect mix of the funny and the heartfelt, “The Edge of Seventeen” is one of the best teen comedies in years.
Starring: Hailee Steinfeld, Haley Lu Richardson, Woody Harrelson
Director: Kelly Fremon Craig
Year: 2016
Runtime: 105 minutes
Rating: R
Rotten Tomatoes Score: 94%

The charming tale of an upper-middle-class teenager who’s spent his entire life avoiding the consequences of his actions, “Ferris Bueller’s Day Off” succeeds in large part due to Matthew Broderick’s charismatic turn in the role of Ferris. He decides to play hooky from school one day, dragging his neurotic best friend, Cameron (Alan Ruck,) and his easygoing girlfriend, Sloane (Mia Sara), along for the ride. A series of misadventures ensues, as the trio makes their way across Chicago, narrowly evading their principal (Jeffrey Jones) and Ferris’ sister (Jennifer Grey), who are both trying to catch them in the act.
Starring: Matthew Broderick, Mia Sara, Alan Ruck
Director: John Hughes
Year: 1986
Runtime: 103 minutes
Rating: PG-13
Rotten Tomatoes Score: 81%

Among the big three silent comedians (Charlie Chaplin, Buster Keaton, and Harold Lloyd), Lloyd was the most charming in a romantic comedy context. In “The Freshman,” he tackles the 1920s trend of college-themed movies, playing an awkward first-year student who resolves to join the football team in a bid to win his crush’s affections. All of Lloyd’s performances are intensely physical, but “The Freshman” is particularly punishing, as he puts his body on the line to achieve a variety of pratfalls on the football field that holds up to this day.
Starring: Harold Lloyd, Jobyna Ralston, James Anderson
Director: Sam Taylor, Fred Newmeyer
Year: 1925
Runtime: 70 minutes
Rating: NR
Rotten Tomatoes Score: 94%

Arguably best known for introducing the internet meme, “Bye, Felicia,” “Friday” is a stoner comedy starring Ice Cube and Chris Tucker. Taking place over the course of one Friday, it’s a slice-of-life narrative about two friends who find themselves in over their heads with a drug dealer. “Friday” was created in part as a response to the many dramatic films released in the early 1990s that focused primarily on violence in urban communities. Its production team sought to bring a comedic, lighthearted sensibility that more closely resembled their own experiences.
Starring: Ice Cube, Chris Tucker, Nia Long
Director: F. Gary Gray
Year: 1995
Runtime: 91 minutes
Rating: R
Rotten Tomatoes Score: 78%

A note-perfect sendup of “Star Trek” (and more importantly, “Star Trek” fandom), “Galaxy Quest” stars Tim Allen as a washed-up ’70s TV star who milks science fiction conventions for all their worth. The rest of the cast from his popular TV show can barely hide how much they loathe him as they’re forced to rehash old grievances at every public appearance. Still, they have to work together when they’re recruited to mediate between two alien races who have received old transmissions of their show and believe them to be real historical records. Funny, heartfelt, and exciting, “Galaxy Quest” is nearly perfect.
Starring: Tim Allen, Sigourney Weaver, Alan Rickman
Director: Dean Parisot
Year: 1999
Runtime: 104 minutes
Rating: PG
Rotten Tomatoes Score: 90%

An ultra-competitive couple (played by Jason Bateman and Rachel McAdams at their most charming) live and die by their organized game nights with their friends. But one day, Brooks (Kyle Chandler) shows up and introduces an element of danger to the festivities, and a murder mystery party ends up involving the gang in actual crime. A perfect blend of action and comedy, “Game Night” takes the audience through a series of hilarious twists and turns. Jesse Plemons gives an incomparable supporting performance as Gary, the oddball neighbor.
Starring: Jason Bateman, Rachel McAdams, Kyle Chandler
Director: John Francis Daley, Jonathan M. Goldstein
Year: 2018
Runtime: 100 minutes
Rating: R
Rotten Tomatoes Score: 85%

In “Gentlemen Prefer Blondes,” Marilyn Monroe and Jane Russell play two showgirls and best friends on a cruise. Lorelei (Monroe) is bubbly, obsessed with diamonds, and way smarter than she looks. Dorothy (Russell) would take a bullet for her friend, even when her social-climbing hijinks get in the way of her opportunity to ogle the entire U.S. men’s Olympic team (in a musical number that is probably one of the most hilariously horny ever committed to celluloid). “Gentlemen” may be in the title, but the biggest joke of the film is that at no point does it seem that Lorelei or Dorothy particularly care what they prefer.
Starring: Marilyn Monroe, Jane Russell, Charles Coburn
Director: Howard Hawks
Year: 1953
Runtime: 91 minutes
Rating: NR
Rotten Tomatoes Score: 98%

When New York City is suddenly plagued by a scourge of malicious ghosts, a trio of misfit scientists start their own small business to meet an obvious need. Thus, the Ghostbusters are born. Although some of the spirits featured in the film are more spooky than others, the efforts of Dan Aykroyd, Bill Murray, and Harold Ramis to keep them in line are always funny. “Ghostbusters” was a massive hit when it was first released, earning nearly $300 million at the box office and spawning several sequels and reboots that stretch to the present day.
Starring: Dan Aykroyd, Bill Murray, Harold Ramis
Director: Ivan Reitman
Year: 1984
Runtime: 107 minutes
Rating: PG
Rotten Tomatoes Score: 97%

When four friends decide to embark on an epic road trip to reconnect in “Girls Trip,” things don’t go exactly as planned. Their various misadventures see them get in scrapes with one another and accidentally hallucinate while drinking absinthe, but their wildly comedic journey only serves to bring them closer together. When speaking with the Hollywood Reporter, writer Tracy Oliver said that she wanted to show “Black women being carefree and having fun just like everybody else,” adding, “I think we need to show all aspects of black lives. I love ‘Moonlight,’ I love ‘Hidden Figures,’ but I also want to see some people who are having fun and just showing female friends hanging out.”
Starring: Regina Hall, Queen Latifah, Jada Pinkett Smith
Director: Malcolm D. Lee
Year: 2017
Runtime: 122 minutes
Rating: R
Rotten Tomatoes Score: 92%

There’s not much funny about the Berlin Wall falling as your mother has a debilitating heart attack that leaves her in a coma. However, “Good Bye Lenin!” manages to find the humor in a son’s desperate, increasingly manic attempts to preserve a slice of East German life for his mother when she wakes up, believing that the shock of a rapidly Westernized, reunited Germany will finish her off. Daniel Brühl puts in a star-making performance, creating a miniature world for his mother to not only shield her from reality but also capture the last melancholy remnants of the flawed but familiar country that has always been his home.
Starring: Daniel Brühl, Katrin Saß, Chulpan Khamatova
Director: Wolfgang Becker
Year: 2003
Runtime: 121 minutes
Rating: R
Rotten Tomatoes Score: 90%

“Groundhog Day” is proof that the wish of having all the time in the world is not all it’s cracked up to be. When a grumpy weatherman (played by Bill Murray, of course) is sent to cover a fluff piece about Groundhog Day, he isn’t exactly thrilled about the assignment. But things get considerably worse when he is forced to relive this single day thousands of times — to the point where he has memorized the actions of every single person in town and learned a host of new skills to pass the time. We’ve seen plenty of time loop movies since, but they all owe a debt of gratitude to the one that started them all.
Starring: Bill Murray, Andie McDowell, Chris Elliot
Director: Harold Ramis
Year: 1993
Runtime: 96 minutes
Rating: PG
Rotten Tomatoes Score: 97%

“There are two ways to live well: You can be smart or pleasant. I’ve been smart for years, and I recommend pleasant.” This is the philosophy of Elwood P. Dowd (James Stewart), the quirky lead of “Harvey.” His family is horrified by his intimate friendship with Harvey, a seemingly imaginary six-foot-tall rabbit that only Dowd can see. The plot descends into screwball comedy as they attempt to have him committed, but “Harvey” has a surprisingly wise and heartwarming message that even in the conformist 1950s, normal is overrated.
Starring: James Stewart, Josephine Hull, Cecil Kellaway
Director: Henry Koster
Year: 1950
Runtime: 104 minutes
Rating: NR
Rotten Tomatoes Score: 86%

A withering anti-social response to John Hughes’ view of teen life in America, “Heathers” stars Winona Ryder as Veronica, a girl who finds herself part of a vacuous clique that she quietly loathes but can’t seem to extricate herself from. That is until J.D. (Christian Slayer) moves to town. His counterculture vibes are a breath of fresh air in monotonous suburbia. However, his rebellion quickly takes on a homicidal edge, and Veronica unwittingly becomes entangled in an accidental murder spree. With its pitch-black, subversive humor, “Heathers” is an open rejection of Ronald Reagan’s 1980s Americana.
Starring: Winona Ryder, Christian Slater, Shannen Doherty
Director: Michael Lehmann
Year: 1989
Runtime: 102 minutes
Rating: R
Rotten Tomatoes Score: 93%

When it comes to screwball comedies from the 1930s and 1940s, Cary Grant is unquestionably your man. In “His Girl Friday,” he plays a cynical newspaper editor who goes a little bit off the rails when he finds out that his ex-wife (Rosalind Russell) is about to get remarried. He uses the promise of a juicy story about a murderer scheduled for execution to lure her back into her fast-paced life as a journalist and, he hopes, a renewed relationship with him. Grant’s chemistry with Russell is off the charts. Together, they make a fine pair in this classic Howard Hawks comedy.
Starring: Cary Grant, Rosalind Russell, Ralph Bellamy
Director: Howard Hawks
Year: 1940
Runtime: 92 minutes
Rating: NR
Rotten Tomatoes Score: 99%

If there’s a dearth of film roles available to Black men right now that don’t fall into racial stereotypes, it was significantly worse in the 1980s. “Hollywood Shuffle” was written in response. Robert Townsend stars as Bobby Taylor, a young man who dreams of becoming an actor. His efforts to find success in Hollywood lead him to grapple with his conscience as he considers taking on poorly-written, racially insensitive roles. Taylor’s concerns are presented as daydreams in which offensive Hollywood demands are exaggerated for comedic effect. One sequence depicts a school that teaches Black actors how to act “more Black” to meet the needs of a white production team. Bitingly witty and still relevant, “Hollywood Shuffle” is one of the best satires of the 1980s.
Starring: Robert Townsend, Anne-Marie Johnson, Starletta DuPois
Director: Robert Townsend
Year: 1987
Runtime: 80 minutes
Rating: R
Rotten Tomatoes Score: 85%

Released in 1990, “House Party” stars Christopher Reid and Christopher Martin (also known as the hip-hop group Kid ‘n Play) as a pair of teenagers determined to throw a rager, even if parents and an inordinate amount of trouble stand in their way. The film features some familiar faces, including Martin Lawrence, George Clinton, and Robin Harris, who tragically died just a few days after the film’s release. Roger Ebert had positive words for the film, writing “the musical is a canvas used by the director, Reginald Hudlin, to show us Black teenagers with a freshness and originality that’s rare in modern movies.”
Starring: Robin Harris, Christopher Reid, Christopher Martin
Director: Reginald Hudlin
Year: 1990
Runtime: 100 minutes
Rating: R
Rotten Tomatoes Score: 93%

A frenetic adventure, “It’s a Mad, Mad, Mad, Mad World” features a cadre of Hollywood stars in a race to lay claim to a hidden fortune. When a dying man reveals the location of a $350,000 stash, the unlikely witnesses to his deathbed confession are left to fight it out. It’s at times an unwieldy comedy, clocking in at nearly three hours (something practically unheard of for the genre), but it hits far more often than it misses. Bosley Crowther of the New York Times described it simply, saying that “So many excellent actors and stunt men do so much in this film that it is beyond my space allowance to begin to credit them.”
Starring: Spencer Tracy, Edie Adams, Milton Berle
Director: Stanley Kramer
Year: 1963
Runtime: 175 minutes
Rating: G
Rotten Tomatoes Score: 70%

A pitch-black comedy with razor-sharp wit, “Kind Hearts and Coronets” shows the lengths to which someone will go when driven by a sense of pride and entitlement. Dennis Price stars as Louis, the son of a well-born woman who disgraced her family by marrying below her station. Raised with a powerful sense of his noble ancestry, Louis decides to take his rightful place as the heir to the family fortune — even if it means killing every relative ahead of him in line! Alec Guinness is especially impressive, playing each of Louis’ many estranged family members. Bosley Crowther of the New York Times wrote of his performance, “The sly and adroit Mr. Guinness plays eight Edwardian fuddy-duds with such devastating wit and variety that he naturally dominates the film.”
Starring: Dennis Price, Alec Guinness, Valerie Hobson
Director: Robert Hamer
Year: 1949
Runtime: 104 minutes
Rating: NR
Rotten Tomatoes Score: 100%

Set during the Korean War (although providing obvious political commentary on the then-ongoing Vietnam War), “MASH” revolves around the doctors and nurses who serve on the front lines at a military hospital. Despite its serious subject matter, Robert Altman’s unique directorial style helps it to succeed as an irreverent comedy. The film proved so popular that it was quickly spun off into a television series. The version of “MASH” that starred Alan Alda and ran for 11 seasons on CBS is perhaps the more famous of the two iterations, but the film stands on its own as a subversive black comedy.
Starring: Donald Sutherland, Elliott Gould, Sally Kellerman
Director: Robert Altman
Year: 1970
Runtime: 116 minutes
Rating: R
Rotten Tomatoes Score: 84%

Released just two years after Bill Murray made his debut as part of the cast of “Saturday Night Live,” “Meatballs” served as proof that he could headline a major motion picture. He stars as Tripper Harrison, a counselor at an under-funded and under-staffed summer camp, who is just trying to get his campers and counselors-in-training back home alive. The film succeeds largely on his talents, with Gary Arnold of the Washington Post saying, “As the seniors boys’ counselor, an easygoing role model, and spontaneous comic genius, Bill Murray of ‘Saturday Night Live’ makes a deceptively sensational debut as a film comedy star.”
Starring: Bill Murray, Chris Makepeace, Kate Lynch
Director: Ivan Reitman
Year: 1979
Runtime: 92 minutes
Rating: PG
Rotten Tomatoes Score: 72%

Thanks to films like “Meet the Fockers,” we’re all familiar with Robert De Niro’s comedic side, but when “Midnight Run” was released in 1988, he was primarily known as a serious film actor. His biggest hits up to that point had been “The Godfather Part II,” “Taxi Driver,” and “Raging Bull” — not exactly laugh riots. “Midnight Run” shows us a different side of the actor, allowing him to flip the script on his traditional tough-guy persona (here he plays a bounty hunter tasked with bringing in a mob accountant) and introduce a little levity to the proceedings. The result is overwhelmingly positive — Vincent Canby of the New York Times referred to De Niro and his costar Charles Grodin as “lunatic delights.”
Starring: Robert De Niro, Charles Grodin, Yaphet Kotto
Director: Martin Brest
Year: 1988
Runtime: 122 minutes
Rating: R
Rotten Tomatoes Score: 94%

By 1936, silent film was all but dead — except, that is, in the eyes of Charlie Chaplin. He was slow to adopt sound, and “Modern Times” proves that he still had a few tricks up his sleeve. Chaplin stars as a harried factory worker who has a breakdown while working the assembly line, culminating in an imaginative sequence in which he becomes caught in the cogs of a machine. “Modern Times” has the pratfalls and slapstick humor one might expect from a Chaplin film, but it’s also a subversive commentary about the burden of modern labor practices on the common worker.
Starring: Charlie Chaplin, Paulette Goddard, Henry Bergman
Director: Charlie Chaplin
Year: 1936
Runtime: 89 minutes
Rating: G
Rotten Tomatoes Score: 98%

Cher and Nicolas Cage might not be an obvious on-screen duo, but as we see in “Moonstruck,” they just sort of make sense together. They both have the same frenetic energy that makes them constantly engaging, even when they’re wildly dysfunctional. In “Moonstruck,” Loretta (Cher) is engaged to marry Johnny (Danny Aiello). When she accidentally falls in love with his hot-headed younger brother Donny (Cage), a baker with one hand and a propensity to fly off the handle, chaos ensues. “Moonstruck” is frequently loud, often aggressive, but always charming.
Starring: Cher, Nicolas Cage, Danny Aiello
Director: Norman Jewison
Year: 1987
Runtime: 101 minutes
Rating: PG
Rotten Tomatoes Score: 94%

If there were only going to be one Monty Python film on this list, it would have to be “Monty Python and the Holy Grail” for the sheer impact it has had on cinematic comedy. It stars Graham Chapman as a perpetually exasperated King Arthur, and it highlights his adventures alongside the Knights of the Round Table as they seek the fabled Holy Grail. Along the way, they encounter significant obstacles, including obstinate Frenchmen, a group of randy maidens at Castle Anthrax, the forbidding Knights Who Say Ni, and, of course, one homicidal rabbit. “Monty Python and the Holy Grail” maintains a lofty position as one of the most frequently quoted comedies of all time.
Starring: Graham Chapman, Eric Idle, Michael Palin
Director: Terry Gilliam, Terry Jones
Year: 1975
Runtime: 90 minutes
Rating: PG
Rotten Tomatoes Score: 97%

Let’s all take a moment to stand in awe of Joe Pesci’s crowning achievement, “My Cousin Vinny.” He has no business being so funny as Vinny, a New York lawyer who is way out of his depth when he travels to the deep South to defend a young relative (Ralph Macchio) who has been charged with murder. There’s absolutely no reason why he should have such electric chemistry with Marisa Tomei (who won an Oscar for her performance), who plays his endlessly clever girlfriend, Mona Lisa. Somehow, he just does, and it all works. There’s not a single line or gesture that isn’t executed for maximum comedic effect in “My Cousin Vinny.”
Starring: Joe Pesci, Marisa Tomei, Ralph Macchio
Director: Jonathan Lynn
Year: 1992
Runtime: 119 minutes
Rating: R
Rotten Tomatoes Score: 86%

During the Great Depression, screwball comedies had a tremendous amount of class consciousness. “My Man Godfrey” is a perfect example. In the film, a wealthy woman (Carole Lombard) adopts the homeless Godfrey (William Powell) to serve as her family’s butler. She intends to help him get off the streets and into a comfortable home, even if her methods are patronizing (and ultimately unnecessary, as we learn that Godfrey is just as rich as her, only living with vagrants to get in touch with the common man). Nevertheless, she ends up falling for him, and the family’s condescending philanthropy is turned on its head. “My Man Godfrey” is one of the best comedies and social commentaries of the 1930s.
Starring: Carole Lombard, William Powell, Alice Brady
Director: Gregory La Cava
Year: 1936
Runtime: 95 minutes
Rating: NR
Rotten Tomatoes Score: 97%

A play on the classic “Dr. Jekyll and Mr. Hyde” story, Jerry Lewis reaches new comedic heights with “The Nutty Professor,” a film he both directed and starred in. He plays a shy, submissive chemistry professor who can’t even prevent his students from pushing him around. That all changes when he invents a serum that instantly transforms him into the ultra-suave (and kind of mean and misogynistic) Buddy Love. 
His alter ego is irresistibly charming and often speculated to be a ruthless parody of Lewis’ frequent on-screen partner, Dean Martin. However, Lewis denied this. He claimed that Buddy Love was “actually a conglomeration of every unkind, nasty son of a b*tch I had seen all of my life. The man who says, ‘Waitress, where the hell is my coffee?’ … the man who takes the cab in the rain from the lady who had her hand on the [door] handle.”
Starring: Jerry Lewis, Stella Stevens, Del Moore
Director: Jerry Lewis
Year: 1963
Runtime: 107 minutes
Rating: NR
Rotten Tomatoes Score: 81%

“The Odd Couple” is pretty much exactly what it says on the tin. Jack Lemmon and Walter Matthau make a very odd couple indeed. When neurotic, fastidious Felix (Lemmon) moves into the bachelor pad of perennial slob Oscar (Matthau), it requires a little bit of an adjustment period for them to figure out how to live together. Their personalities and lifestyles clash in the most hilarious ways. The duo made such an impression that they would team up again decades later as the titular “Grumpy Old Men” in the 1990s.
Starring: Jack Lemmon, Walter Matthau, John Fiedler
Director: Gene Saks
Year: 1968
Runtime: 105 minutes
Rating: G
Rotten Tomatoes Score: 97%

An ode to the sheer pointlessness of office culture, “Office Space” speaks to everyone who has ever fantasized about quitting their day job. Ron Livingston stars as Peter, an office drone who quietly hates his life until his girlfriend convinces him to attend a hypnosis session. When the hypnotist suffers a fatal heart attack before waking him from his trance, Peter is stuck with a relaxed, devil-may-care attitude towards his job. Surprisingly, this makes his bosses respect him even more, perceiving him as a straight shooter. Full of great comedic moments (including the gangster-style execution of a perpetually malfunctioning printer), “Office Space” has grown in relevance since its release.
Starring: Ron Livingston, Jennifer Aniston, David Herman
Director: Mike Judge
Year: 1999
Runtime: 89 minutes
Rating: R
Rotten Tomatoes Score: 80%

Once upon a time, Pee-wee Herman (played by Paul Reubens) was everyone’s favorite naïve man child. In “Pee-wee’s Big Adventure,” our intrepid hero embarks on a cross-country adventure in search of his beloved bike, which has gone missing, much to Pee-wee’s consternation. The entire production exists in a heightened reality, from the childlike feud between Herman and his ultimate nemesis Francis to his madcap escapade on a Hollywood set to his legitimately frightening encounter with the terrifying truck-driving ghost Large Marge. Director Tim Burton imbues this sweet film with a strange sense of menace that lies just beneath its candy-coated exterior, making “Pee-wee’s Big Adventure” equal parts charming and unsettling.
Starring: Paul Reubens, E.G. Daily, Diane Salinger
Director: Tim Burton
Year: 1985
Runtime: 90 minutes
Rating: PG
Rotten Tomatoes Score: 87%

In 1987 you could simply put Steve Martin and John Candy on-screen together, and it would be funny. The two play an unlikely duo in “Planes, Trains and Automobiles,” the classic story of two very different men desperately trying to get home for the holidays. Straight-laced Neal Page (Martin) has had his flight rerouted at the last minute, putting his Thanksgiving plans with his wife and children in jeopardy. The last thing in the world he needs is to end up with the good-hearted but obnoxious Del Griffith (Candy) — but that’s what happens. Despite their differences, they have to work together to make it back home for the holiday.
Starring: Steve Martin, John Candy, Laila Robins
Director: John Hughes
Year: 1987
Runtime: 92 minutes
Rating: R
Rotten Tomatoes Score: 92%

If there’s any single entity ripe for parody, it’s the self-important performing artist who is ultra-convinced of their own talent. “Popstar: Never Stop Never Stopping” stars Andy Samberg as Conner (aka Conner4Real), the former frontman of the wildly successful pop-rap group the Style Boyz, who goes solo. The film chronicles his seemingly endless series of poor decisions — creative, professional, and romantic. “Popstar: Never Stop Never Stopping” is held together by Conner’s relentless optimism and a soundtrack full of note-perfect comedy musical numbers.
Starring: Andy Samberg, Akiva Schaffer, Jorma Taccone
Director: Akiva Schaffer, Jorma Taccone
Year: 2016
Runtime: 86 minutes
Rating: R
Rotten Tomatoes Score: 79%

When Judy Benjamin’s (Goldie Hawn) new husband dies suddenly while in the middle of sex, she decides to take her life in a different direction. Thanks to a fortuitous conversation with a military recruiter, the pampered, indoorsy woman joins the Army. That’s the basic plot of “Private Benjamin.” Judy is a fish out of water as she tries to make her way through boot camp. While “Private Benjamin” laughs with Judy, it restrains itself from laughing at her. Hawn is too unrelentingly charming to be the subject of mockery for long, and her journey ultimately leads her to self-discovery.
Starring: Goldie Hawn, Eileen Brennan, Armand Assante
Director: Howard Zieff
Year: 1980
Runtime: 109 minutes
Rating: R
Rotten Tomatoes Score: 82%

In Mel Brooks’ “The Producers,” Leopold Bloom (Gene Wilder) and Max Bialystock (Zero Mostel) come up with a foolproof plan: They will produce a Broadway show so bad that it’s guaranteed to flop, and they’ll make a killing because they never have to pay back their investors. The result? “Springtime for Hitler,” a garish, campy ode to the Third Reich that is in appallingly poor taste. But when it becomes a surprise hit, disaster looms for the suddenly successful theater producers. Wilder and Mostel are at the top of their game, bouncing off each other with the wit and precision of seasoned vaudeville performers.
Starring: Gene Wilder, Zero Mostel, Kenneth Mars
Director: Mel Brooks
Year: 1968
Runtime: 88 minutes
Rating: NR
Rotten Tomatoes Score: 90%

Whenever the Coen brothers are involved, you know two things for certain: There’s going to be crime, and it’s probably going to be hilarious. That’s what we get in “Raising Arizona,” an off-kilter romantic comedy that showcases Nicolas Cage and Holly Hunter at their absolute best. Cage is a petty criminal who can’t stop getting arrested. Hunter is a police officer who falls in love with him in spite of herself. They marry, but when they are unable to conceive, they land upon a perfect solution: They’ll kidnap one of the quintuplets that have been in the news recently. After all, with five babies, what are the odds that someone would notice one missing? This plan goes as poorly as you might expect, but it’s a perfect disaster that makes an entertaining movie.
Starring: Nicolas Cage, Holly Hunter, John Goodman
Director: Joel Coen
Year: 1987
Runtime: 93 minutes
Rating: PG-13
Rotten Tomatoes Score: 92%

Eccentric indie auteur Wes Anderson’s second film, “Rushmore,” was a massive critical success that put the director on the map. It stars Jason Schwartzman as Max Fischer, a precocious teenager who is incredibly invested in a variety of extracurricular activities at his prep school despite being on the verge of flunking out. While he attempts to mount his theatrical opus on the high school stage, he finds himself falling in love with elementary school teacher Rosemary Cross (Olivia Williams). Max’s crush brings him into conflict with his curmudgeonly, older friend (Bill Murray), who happens to also be romantically interested in her. Come for Murray’s quiet exasperation with his annoying teenage sons, and stay for the priceless exchange in which Dr. Peter Flynn (Luke Wilson) says, “These are O.R. scrubs,” to which Max replies, “O.R. they?”
Starring: Jason Schwartzman, Bill Murray, Olivia Williams
Director: Wes Anderson
Year: 1998
Runtime: 93 minutes
Rating: R
Rotten Tomatoes Score: 89%

When deadbeat rocker Dewey (Jack Black) takes on a substitute teaching job in a desperate bid to earn enough money to keep his roommate off his back, he discovers a classroom full of elementary school students waiting to be transformed into a pint-sized rock band. Thus, the “School of Rock” is born. Jack Black was born for the role of a deeply dysfunctional mentor who offers a sense of chaos mixed with his genuine support for his students. “School of Rock” wouldn’t be the outright classic that it is without its deep bench of young actors, all of whom are strong performers and preternaturally talented musicians.
Starring: Jack Black, Joan Cusack, Mike White
Director: Richard Linklater
Year: 2003
Runtime: 108 minutes
Rating: PG-13
Rotten Tomatoes Score: 92%

The first entry in Edgar Wright’s Cornetto trilogy, “Shaun of the Dead” is a comedic take on the traditional zombie film. Shaun (Simon Pegg) doesn’t have a lot going for him. He works a dead-end job and seems to be perpetually disappointing his girlfriend, Liz (Kate Ashfield), who wants them to take the next step in their lives together. Luckily (or unluckily), Shaun gets the perfect opportunity to prove himself when zombies descend upon their town, and he and his best friend, Ed (Nick Frost), must step up to defend the people they care about. Sweet, scary, and genuinely funny, “Shaun of the Dead” is a true original.
Starring: Simon Pegg, Nick Frost, Lucy Davis
Director: Edgar Wright
Year: 2004
Runtime: 97 minutes
Rating: R
Rotten Tomatoes Score: 92%

In this classic Buster Keaton silent film, the stone-faced comedian stars as a young projectionist who daydreams constantly about being a famous detective and wooing the woman of his dreams. “Sherlock Jr” features plenty of Keaton’s trademark stunts and practical effects, including a notable fantasy sequence in which he is transported into the world of the film. The scenes keep changing around him so that one minute he’s standing in a peaceful garden, the next in front of a speeding train. 
Starring: Buster Keaton, Kathryn McGuire, Ward Crane
Director: Buster Keaton
Year: 1924
Runtime: 48 minutes
Rating: NR
Rotten Tomatoes Score: 92%

In 1986, director Spike Lee hadn’t been proclaimed the next big thing yet. All he had was this little film, “She’s Gotta Have It,” which despite barely getting funded, became one of the cornerstones of the independent film movement of the late 1980s and early 1990s. It stars Tracy Camilla Johns as Nola, a sexually-liberated woman who isn’t particularly interested in monogamy. In the film, she dates three men at the same time, partially because she finds different qualities appealing in each of them but also because she doesn’t feel the desire to be tied down to just one person. Although it has some problematic elements (Lee himself has said that his one directorial regret is a sequence in this film), for the most part, it’s a breezy, endearing introduction to his career.
Starring: Tracy Camilla Johns, Tommy Redmond Hicks, John Canada Terrell
Director: Spike Lee
Year: 1986
Runtime: 84 minutes
Rating: R
Rotten Tomatoes Score: 94%

You would be forgiven for considering “Singin’ in the Rain” just a musical. After all, it is one of the very best of that genre. But as a parody of old Hollywood, especially in its depiction of silent film diva, Lina Lamont (Jean Hagen), it packs more humor into its runtime than many movies that are promoted as straight comedies. Lina, with her boorish behavior and comically screechy voice ill-suited for the transition to talkies, and perpetually quipping sidekick, Cosmo Brown (Donald O’Connor), provide plenty to laugh at in between musical numbers.
Starring: Gene Kelly, Donald O’Connor, Debbie Reynolds
Director: Stanley Donen, Gene Kelly
Year: 1952
Runtime: 102 minutes
Rating: G
Rotten Tomatoes Score: 100%

It just makes sense. If you’re hiding from the Mob, a nunnery has to be the last place they would think to look, right? Anyway, that’s the logic in “Sister Act.” When Deloris (Whoopi Goldberg) witnesses a murder, she is swiftly whisked away for her protection, posing as the newest nun in a convent in California. The quiet life doesn’t particularly suit her, but she finds an unexpected outlet in running the convent’s choir. “Sister Act” was a massive hit at the box office, ultimately earning over $230 million worldwide — not bad for a relatively inexpensive production with a budget of $31 million.
Starring: Whoopi Goldberg, Maggie Smith, Kathy Najimy
Director: Emile Ardolino
Year: 1992
Runtime: 100 minutes
Rating: PG
Rotten Tomatoes Score: 74%

The third collaboration between director George Roy Hill and actor Paul Newman, “Slap Shot” is a quintessential sports comedy. Set in a Rust Belt factory town whose best days are far behind it, the film follows the exploits of a local hockey team that is willing to resort to desperate (and violent) measures to win. Newman stars as the team’s goalie and coach, who encourages his team to play as dirty as they can — even by the standards of hockey, a sport that can be notoriously brutal. Although it received mixed reviews when it was first released, it has since grown to become a cult classic. Dan Epstein of Rolling Stone called it “the greatest sports flick of the 1970s.”
Starring: Paul Newman, Michael Ontkean, Lindsay Crouse
Director: George Roy Hill
Year: 1977
Runtime: 123 minutes
Rating: R
Rotten Tomatoes Score: 83%

What can you say about “Some Like It Hot” except that it might just be a perfect comedy? Tony Curtis and Jack Lemmon star as two musicians who have to pose as women and flee to Florida in a girls’ band after running afoul of the Chicago Mob in the roaring ’20s. Of course, it doesn’t take long before Joe (Curtis), posing as a sexually repressed heir to an oil fortune begins to woo lead singer Sugar (Monroe). A perfect blend of physical comedy and wit, Roger Ebert called “Some Like it Hot,” “One of the enduring treasures of the movies, a film of inspiration and meticulous craft.”
Starring: Tony Curtis, Jack Lemmon, Marilyn Monroe
Director: Billy Wilder
Year: 1959
Runtime: 120 minutes
Rating: NR
Rotten Tomatoes Score: 94%

Change is never easy, especially if you’re two emotionally-stunted men in your 40s who find yourselves sharing a room with your new stepbrother. In “Step Brothers,” Will Ferrell and John C. Reilly play a hilariously hostile duo, wildly resentful of each other and the fact that their retiree parents have suddenly gotten married and changed the dynamics of their home lives. Packed full of brilliant one-liners and a surprising amount of heart, “Step Brothers” is a delightfully raucous comedy that allows both actors to truly let loose.
Starring: Will Ferrell, John C. Reilly, Mary Steenburgen
Director: Adam McKay
Year: 2008
Runtime: 95 minutes
Rating: R
Rotten Tomatoes Score: 55%

“The Sting” is arguably the best heist film in the history of cinema. Every step of the way, it’s so perfectly thought out that you can’t help but stand in awe of it. Yet, one thing that frequently gets overlooked is how genuinely funny it is. Robert Redford stars as a two-bit grifter who enlists the aid of the retired Henry Gondorff (Paul Newman) to pull a massive con job on Doyle Lonnegan (Robert Shaw), an Irish mobster. If you want to see perfect comedic timing, watch the sequence in which Gondorff poses as a drunk and enters into a poker game with Lonnegan intending to annoy him almost to the point of speechlessness and then cheating him out of thousands of dollars. They don’t make them like this anymore.
Starring: Paul Newman, Robert Redford, Robert Shaw
Director: George Roy Hill
Year: 1973
Runtime: 129 minutes
Rating: PG
Rotten Tomatoes Score: 94%

In Depression-era Los Angeles, John L. Sullivan (Joel McCrea) is a famous movie director who suddenly realizes how out of touch he is with the common man. On a whim, he decides to ride the rails as a transient. To his surprise, he finds himself ill-equipped to cope with the realities of life outside the bubble of glamorous Hollywood. The situation is made all the more difficult when he is knocked unconscious, loses his memory, and ends up working on a chain gang. “Sullivan’s Travels” is packed full of wry humor and insightful social commentary.
Starring: Joel McCrea, Veronica Lake, Robert Warwick
Director: Preston Sturges
Year: 1941
Runtime: 91 minutes
Rating: NR
Rotten Tomatoes Score: 100%

There are exactly three things that separate “The Thin Man” from every other film: One is the incredible, crackling energy that floats between its stars, William Powell and Myrna Loy, who play a married detective couple. The second is the fast-paced, clever dialogue that they shoot back and forth throughout the film. It’s quick enough to give you whiplash if you’re not careful. The third is the presence of Asta the Wire Fox Terrier (played by Skippy), who was a stalwart of cinema in the 1930s but was rarely utilized as well as she is here. A great couple, snappy dialogue, and an adorable dog — what more could you ask for?
Starring: William Powell, Myrna Loy, Maureen O’Sullivan
Director: W.S. Van Dyck II
Year: 1934
Runtime: 93 minutes
Rating: NR
Rotten Tomatoes Score: 98%

It’s a mark of a truly great comedy when some of its bits become engrained in popular culture. “This Is Spinal Tap” doesn’t just have one or two truly great, endlessly quotable moments — it’s filled with them. Of course, you have the amps that go up to 11 in case you need the music to be loud. You’ve got the iconic image of a comically small Stonehenge monument being lowered onto the stage with great ceremony. And there is the endless procession of drummers meeting untimely deaths. But “This Is Spinal Tap” is also peppered with delightful one-liners that you only catch on your third or even 10th viewing.
Starring: Michael McKean, Christopher Guest, Harry Shearer
Director: Rob Reiner
Year: 1984
Runtime: 82 minutes
Rating: R
Rotten Tomatoes Score: 95%

It’s kind of fun that “Three Amigos” is on this list alongside “Galaxy Quest” because, in a lot of ways, the latter wouldn’t have been made without the former. In “Three Amigos,” a trio of silent-era Western stars is hired by a Mexican woman to protect her small village from an outlaw. The Amigos think that this is an acting gig — all for show — never realizing that they are expected to be the heroes they portray onscreen. With a great line-up of Steve Martin, Martin Short, and Chevy Chase (three of the biggest names in comedy at the time), “Three Amigos” won the hearts of 1980s audiences.
Starring: Steve Martin, Martin Short, Chevy Chase
Director: John Landis
Year: 1986
Runtime: 105 minutes
Rating: PG
Rotten Tomatoes Score: 45%

It’s not the easiest thing in the world to make a comedy about Nazis, especially while World War II was still raging. However, famed director Ernst Lubitsch works his magic with “To Be or Not to Be” and somehow pulls it off. The film stars Carole Lombard and Jack Benny as the two leads in a Polish theatre troupe who get mixed up in a resistance plot and have to use all their acting skills to pull one over on the inept Nazis who have just invaded. The genius of “To Be or Not to Be” is in taking terror away from the Nazis and turning the ominous stormtroopers into incompetent bureaucrats who are too intimidated by their superiors to avoid being outwitted by the resourceful actors.
Starring: Carole Lombard, Jack Benny, Robert Stack
Director: Ernst Lubitsch
Year: 1942
Runtime: 109 minutes
Rating: NR
Rotten Tomatoes Score: 96%

When you’re a demanding Method actor who has alienated everyone in the New York theatre community, what options do you have but to pretend to be a middle-aged Southern actress to finagle a role on a daytime soap opera? That’s the plot of “Tootsie.” Dustin Hoffman stars, playing both the pretentious Michael Dorsey as well as his drawling, tough-as-nails female counterpart, Dorothy Michaels. As Dorothy, Michael encounters the challenges and everyday harassment that women have to put up with. This gives him fresh insight into gender politics. “Tootsie” was nominated for 10 Academy Awards, Jessica Lange winning for best supporting actress as Hoffman’s soap costar and love interest.
Starring: Dustin Hoffman, Jessica Lange, Teri Garr
Director: Sydney Pollack
Year: 1982
Runtime: 111 minutes
Rating: PG
Rotten Tomatoes Score: 90%

What happens when two conniving old billionaires (Ralph Bellamy and Don Ameche) decide to perform their own private social experiments? “Trading Places” happens. To determine whether morality is born into a person through good breeding, or if education and socioeconomic advantages teach someone how to be decent, they use two very different men as guinea pigs. They take the wealthy Louis (Dan Aykroyd) and essentially drop him into the gutter, and they invite small-time grifter Billy Ray (Eddie Murphy) to join their stockbroking firm. And just like that, comedy ensues, as the pair eventually discover the source of the scheme and seek their revenge.
Starring: Dan Aykroyd, Eddie Murphy, Jamie Lee Curtis
Director: John Landis
Year: 1983
Runtime: 116 minutes
Rating: R
Rotten Tomatoes Score: 88%

The film that launched a franchise filled with Chevy Chase’s misadventures and a perpetually rotating cast of Griswold children (Rusty and Audrey were famously never played by the same actors twice), “National Lampoon’s Vacation” is a tale of a family road trip gone laughably wrong. Desperate to take his wife and kids to Walley World, a popular yet extremely kitschy amusement park, Clark Griswold (Chase) drags them across the country, and things go from bad to worse. After their grueling (and hilarious) journey, the Griswolds finally arrive at Walley World … and it’s closed for repairs!
Starring: Chevy Chase, Beverly D’Angelo, Randy Quaid
Director: Harold Ramis
Year: 1983
Runtime: 98 minutes
Rating: R
Rotten Tomatoes Score: 93%

Based on a recurring “Saturday Night Live” sketch featuring Mike Myers and Dana Carvey as the hosts of a public access television show, “Wayne’s World” quickly took on a life of its own. Wayne (Myers) and Garth (Carvey) are rock enthusiasts who are perfectly content just sharing their love of music on their show and partying their nights away. One day, studio executive Benjamin Kane (Rob Lowe) shows up and tries to turn their beloved “Wayne’s World” program into something it isn’t. Together, they fight to save their show, famously headbanging to Queen’s “Bohemian Rhapsody” along the way.
Starring: Mike Myers, Dana Carvey, Tia Carrere
Director: Penelope Spheeris
Year: 1992
Runtime: 95 minutes
Rating: PG-13
Rotten Tomatoes Score: 78%

During the 1990s, Adam Sandler was very big into screamy, over-the-top characters with a comically short fuse. That made films like “Happy Gilmore” a success, but what we get in “The Wedding Singer” is a refreshingly toned-down version of his patented schtick. He stars as an affable wedding singer who is left at the altar and finds himself falling in love with a waitress (Drew Barrymore), who just happens to be engaged to a sleazy stockbroker. Sandler and Barrymore are magnetic together, and the fact that they make a genuinely good on-screen couple is one of the film’s most pleasant surprises.
Starring: Adam Sandler, Drew Barrymore, Christine Taylor
Director: Frank Coraci
Year: 1998
Runtime: 96 minutes
Rating: PG-13
Rotten Tomatoes Score: 69%

Drawing heavily on screwball comedies from the 1930s and 1940s, “What’s Up, Doc?” stars Ryan O’Neal as a musicologist who is unhappily married to his neurotic wife (played by the incomparable Madeline Kahn). While on a work trip to San Francisco, he meets the charming but unpredictable Judy (Barbra Streisand). Chaos ensues when they and two other guests at their hotel have the same luggage and find themselves accidentally absconding with one another’s suitcases, leading to each desperately trying to track down their missing possessions. James Berardinelli of ReelViews gave special praise to director Peter Bogdonavich’s contributions to the film, saying, “Only a director in complete control can fashion something so effortlessly chaotic.”
Starring: Barbra Streisand, Ryan O’Neal, Madeline Kahn
Director: Peter Bogdonavich
Year: 1972
Runtime: 94 minutes
Rating: G
Rotten Tomatoes Score: 89%

Love at first sight is overrated. What we have in “When Harry Met Sally” is the slowest of slow burns in terms of romance. Harry (Billy Crystal) and Sally (Meg Ryan) meet straight out of college, but it takes at least a decade for them to grow from somewhat hostile acquaintances to friends to lovers. Still, their chemistry is there from the very beginning, and that (along with truly excellent supporting performances from Bruno Kirby and Carrie Fisher, the two greatest wingmen on the planet) is why “When Harry Met Sally” remains one of the most charming romantic comedies of all time.
Starring: Billy Crystal, Meg Ryan, Carrie Fisher
Director: Rob Reiner
Year: 1989
Runtime: 95 minutes
Rating: R
Rotten Tomatoes Score: 91%

Starring Richard. E Grant and Paul McCann as two struggling young actors, “Withnail and I” is a window into life in Britain in the early 1980s. With their flat in complete ruin and their careers more or less permanently stalled, they take a trip to the country that is not without its own problems. The film succeeds on the strength of the two lead performances (it’s especially remarkable that this is Grant’s feature film debut) and the intensely quotable dialogue that brings these two misfits to life.
Starring: Richard E. Grant, Paul McGann, Richard Griffiths
Director: Bruce Robinson
Year: 1987
Runtime: 102 minutes
Rating: R
Rotten Tomatoes Score: 94%

In “Women on the Verge of a Nervous Breakdown,” one of director Pedro Almodóvar’s most successful early productions, Carmen Maura stars as a voiceover artist who finds herself being unceremoniously left by her long-term boyfriend, Ivan. As she sets off in search of an explanation from Ivan, she is caught up in a seemingly endless series of surreal encounters. Along with many other critics, Michael Wilmington of the Chicago Tribune gave it a positive review, calling it “a feminist comedy with real bite; it always brings down the house.”
Starring: Antonio Banderas, Carmen Maura, Julieta Serrano
Director: Pedro Almodóvar
Year: 1988
Runtime: 88 minutes
Rating: R
Rotten Tomatoes Score: 90%

You know you’ve made it into the realm of literary classics when you get a bona fide movie parody of your seminal work — directed by Mel Brooks, no less. “Young Frankenstein” stars Gene Wilder as a descendant of the infamous Victor Frankenstein who is convinced he’s just a normal, ordinary doctor, and has answered quite enough questions about his kooky, grave-robbing ancestor, thank you very much. While on a trip to the family castle, he becomes obsessed with reanimating a corpse — an accomplishment he achieves with hilariously mixed results, aided by a note-perfect Marty Feldman as the notorious lab assistant Igor.
Starring: Gene Wilder, Marty Feldman, Peter Boyle
Director: Mel Brooks
Year: 1974
Runtime: 105 minutes
Rating: PG
Rotten Tomatoes Score: 94%

What can we say? Sometimes there’s more to life than being really, really, ridiculously good-looking. “Zoolander” doesn’t always get the credit it deserves as a delightful early 2000s comedy, but Ben Stiller is fantastic as the hapless Derek Zoolander. A male model, Zoolander’s problems largely revolve around a lack of respect from his coal-mining father, the death of his roommates in a tragic “gas fight,” and his devastating inability to turn left on the catwalk. His life gets considerably more complicated when an evil fashion designer (played by Will Ferrell — who else?) brainwashes him to murder the Prime Minister of Malaysia. Packed full of fantastic one-liners and a great supporting turn from Owen Wilson, “Zoolander” is endlessly entertaining.
Starring: Ben Stiller, Owen Wilson, Will Ferrell
Director: Ben Stiller
Year: 2001
Runtime: 89 minutes
Rating: PG-13
Rotten Tomatoes Score: 64%

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