The Best Comedies I've Ever Seen
by ctownfilm | created - 15 Jul 2015 | updated - 04 Aug 2015 | Public(a new-school list)
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1. Knocked Up (2007)
R | 129 min | Comedy, Romance
For fun-loving party animal Ben Stone, the last thing he ever expected was for his one-night stand to show up on his doorstep eight weeks later to tell him she's pregnant with his child.
Director: Judd Apatow | Stars: Seth Rogen, Katherine Heigl, Paul Rudd, Leslie Mann
Votes: 384,739 | Gross: $148.73M
No other comedy I've seen has been able to mix pathos and TRULY laugh-out-loud bits on a recognizably human scale to the soaring heights that Knocked Up does. Honestly, that's a miracle, and should be cherished. Knocked Up is a perfect comedy.
2. White Men Can't Jump (1992)
R | 115 min | Comedy, Sport
Black and white basketball hustlers join forces to double their chances of winning money on the street courts and in a basketball tournament.
Director: Ron Shelton | Stars: Wesley Snipes, Woody Harrelson, Rosie Perez, Tyra Ferrell
Votes: 98,338 | Gross: $76.25M
What an exhilarating comedy. It can be funny, dangerous, pointed, and then goofy as hell in a matter of seconds. The great achievement in that is that it all feels so VITAL. White Men Can't Jump is a comedy about what it means to be a man, racial divides, honor and morality. Heady stuff. It also hawks bizarrely golden lines like "You can put a cat in the oven, but that don't make it a biscuit."
3. Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb (1964)
PG | 95 min | Comedy, War
An unhinged American general orders a bombing attack on the Soviet Union, triggering a path to nuclear holocaust that a war room full of politicians and generals frantically tries to stop.
Director: Stanley Kubrick | Stars: Peter Sellers, George C. Scott, Sterling Hayden, Keenan Wynn
Votes: 518,446 | Gross: $0.28M
The only obligatory(though earned) "film school approved" comedy on my list. Dr. Strangelove is a hilarious satire. It's pitch black and even goes as far to be unnerving. Dr. Strangelove attacked barely veiled anxieties with aggression and precision - and to do it with not so much as a remove from the era it was holding a mirror to... that's bold.
4. The Jerk (1979)
R | 94 min | Comedy
A simpleminded, sheltered country boy suddenly decides to leave his family home to experience life in the big city, where his naivete is both his best friend and his worst enemy.
Director: Carl Reiner | Stars: Steve Martin, Bernadette Peters, Catlin Adams, Mabel King
Votes: 64,236 | Gross: $73.69M
The first comedy I ever saw to make me think "this is what comedy is supposed to be." What that meant to me at the time, was this feeling of cheeky anarchy... like I was getting away with something by enjoying the cracked humor of The Jerk. It's totally off the wall, and it has a try-anything sensibility that holds nothing sacred. It's comedy in a most-distilled form. It's pure funny.
5. Chasing Amy (1997)
R | 113 min | Comedy, Drama, Romance
Holden and Banky are comic book artists. Everything's going good for them until they meet Alyssa, also a comic book artist. Holden falls for her, but his hopes are crushed when he finds out she's a lesbian.
Director: Kevin Smith | Stars: Ben Affleck, Joey Lauren Adams, Ethan Suplee, Scott Mosier
Votes: 143,834 | Gross: $12.02M
Chasing Amy marches right up to the border separating comedy from drama - it's not so much hilarious, as it is wise and humane. That counts for something.
6. Everything You Always Wanted to Know About Sex * But Were Afraid to Ask (1972)
R | 88 min | Comedy
Seven stories are trying to answer the question: what is sex? Or maybe they are not trying.
Director: Woody Allen | Stars: Woody Allen, Gene Wilder, Louise Lasser, John Carradine
Votes: 41,800
I feel as though this is still somewhat progressive, which is telling for a film 4 decades old. I saw this at a formative time in my life, and it resonated sharply. It was frank unlike anything I had seen, and tackled taboos with refreshing wit and aplomb.
7. The 40-Year-Old Virgin (2005)
R | 116 min | Comedy, Romance
Goaded by his buddies, a nerdy guy who's never "done the deed" only finds the pressure mounting when he meets a single mother.
Director: Judd Apatow | Stars: Steve Carell, Catherine Keener, Paul Rudd, Romany Malco
Votes: 467,282 | Gross: $109.45M
I've never laughed harder in a theater than the first time I saw 40YOV. It's influenced a decade, a sort of golden age renaissance, of screen comedies.
8. Observe and Report (2009)
R | 86 min | Action, Comedy, Crime
Bi-polar mall security guard Ronnie Barnhardt is called into action to stop a flasher from turning shopper's paradise into his personal peep show. But when Barnhardt can't bring the culprit to justice, a surly police detective is recruited to close the case.
Director: Jody Hill | Stars: Seth Rogen, Anna Faris, Ray Liotta, Michael Peña
Votes: 65,295 | Gross: $23.99M
Unbelievably brutal, but there's something that's quite beautiful about that. O & R is balls-out bonkers, and that needs to be encouraged more... its really more audacious than anything, but it succeeds in it's lofty goal of making us laugh and squirm.
9. Swingers (1996)
R | 96 min | Comedy, Drama
A wannabe actor has a hard time moving on from a break-up, but he is lucky to have supportive friends.
Director: Doug Liman | Stars: Vince Vaughn, Heather Graham, Jon Favreau, Ron Livingston
Votes: 88,159 | Gross: $4.51M
Swingers, like a lot of other films on this list, mixes heart and humor. Swingers is a time-capsule film that resonates today because it finds relatability in hard-won truths about the nature of love and male friendship.
10. Valley Girl (1983)
R | 99 min | Comedy, Romance
Julie, a girl from the valley, meets Randy, a punk from the city. They are from different worlds and find love. Somehow they need to stay together in spite of her trendy, shallow friends.
Director: Martha Coolidge | Stars: Nicolas Cage, Deborah Foreman, Elizabeth Daily, Michael Bowen
Votes: 18,445 | Gross: $16.80M
What separates Valley Girl from other 80's comedies, is honesty. Again, another film that's not so much hilarious, but rather offers much more in the way of human-scaled rewards.
11. This Is Spinal Tap (1984)
R | 82 min | Comedy, Music
Spinal Tap, one of England's loudest bands, is chronicled by film director Marty DiBergi on what proves to be a fateful tour.
Director: Rob Reiner | Stars: Rob Reiner, Michael McKean, Christopher Guest, Kimberly Stringer
Votes: 147,397 | Gross: $4.74M
12. The Royal Tenenbaums (2001)
R | 110 min | Comedy, Drama
The eccentric members of a dysfunctional family reluctantly gather under the same roof for various reasons.
Director: Wes Anderson | Stars: Gene Hackman, Gwyneth Paltrow, Anjelica Huston, Ben Stiller
Votes: 313,286 | Gross: $52.36M
13. Superbad (2007)
R | 113 min | Comedy
Two co-dependent high school seniors are forced to deal with separation anxiety after their plan to stage a booze-soaked party goes awry.
Director: Greg Mottola | Stars: Michael Cera, Jonah Hill, Christopher Mintz-Plasse, Bill Hader
Votes: 633,051 | Gross: $121.46M
14. The Squid and the Whale (2005)
R | 81 min | Comedy, Drama
Follows two young boys dealing with their parents' divorce in Brooklyn in the 1980s.
Director: Noah Baumbach | Stars: Owen Kline, Jeff Daniels, Laura Linney, Jesse Eisenberg
Votes: 90,461 | Gross: $7.36M
15. Young Frankenstein (1974)
PG | 106 min | Comedy
An American grandson of the infamous scientist, struggling to prove that his grandfather was not as insane as people believe, is invited to Transylvania, where he discovers the process that reanimates a dead body.
Director: Mel Brooks | Stars: Gene Wilder, Madeline Kahn, Marty Feldman, Peter Boyle
Votes: 168,936 | Gross: $86.30M
16. The Descendants (2011)
R | 115 min | Comedy, Drama
A land baron tries to reconnect with his two daughters after his wife is seriously injured in a boating accident.
Director: Alexander Payne | Stars: George Clooney, Shailene Woodley, Amara Miller, Nick Krause
Votes: 251,863 | Gross: $82.58M
17. This Is the End (2013)
R | 107 min | Comedy, Fantasy
Six Los Angeles celebrities are stuck in James Franco's house after a series of devastating events just destroyed the city. Inside, the group not only have to face the apocalypse, but themselves.
Directors: Evan Goldberg, Seth Rogen | Stars: James Franco, Jonah Hill, Seth Rogen, Jay Baruchel
Votes: 435,058 | Gross: $101.47M
18. Benny & Joon (1993)
PG | 98 min | Comedy, Drama, Romance
A mentally ill young woman finds her love in an eccentric man who models himself after Buster Keaton.
Director: Jeremiah S. Chechik | Stars: Johnny Depp, Mary Stuart Masterson, Aidan Quinn, Julianne Moore
Votes: 62,101 | Gross: $23.20M
19. O Brother, Where Art Thou? (2000)
PG-13 | 107 min | Comedy, Crime, Drama
In the deep south during the 1930s, three escaped convicts search for hidden treasure while a relentless lawman pursues them.
Directors: Joel Coen, Ethan Coen | Stars: George Clooney, John Turturro, Tim Blake Nelson, John Goodman
Votes: 330,962 | Gross: $45.51M
20. Step Brothers (2008)
R | 98 min | Comedy
Two aimless middle-aged losers still living at home are forced against their will to become roommates when their parents marry.
Director: Adam McKay | Stars: Will Ferrell, John C. Reilly, Mary Steenburgen, Richard Jenkins
Votes: 319,144 | Gross: $100.47M
21. 50/50 (2011)
R | 100 min | Comedy, Drama, Romance
Inspired by a true story, a comedy centered on a 27-year-old guy who learns of his cancer diagnosis and his subsequent struggle to beat the disease.
Director: Jonathan Levine | Stars: Joseph Gordon-Levitt, Seth Rogen, Anna Kendrick, Bryce Dallas Howard
Votes: 342,977 | Gross: $35.01M
22. Fast Times at Ridgemont High (1982)
R | 90 min | Comedy, Drama
A group of Southern California high school students are enjoying their most important subjects: sex, drugs and rock n' roll.
Director: Amy Heckerling | Stars: Sean Penn, Jennifer Jason Leigh, Judge Reinhold, Robert Romanus
Votes: 115,810 | Gross: $27.09M
23. The Informant! (2009)
R | 108 min | Biography, Comedy, Crime
The U.S. government decides to go after an agro-business giant with a price-fixing accusation, based on the evidence submitted by their star witness, vice president-turned-informant Mark Whitacre.
Director: Steven Soderbergh | Stars: Matt Damon, Tony Hale, Patton Oswalt, Lucas McHugh Carroll
Votes: 67,462 | Gross: $33.31M
24. Sideways (2004)
R | 127 min | Comedy, Drama, Romance
Two men reaching middle age with not much to show but disappointment embark on a week-long road trip through California's wine country, just as one is about to take a trip down the aisle.
Director: Alexander Payne | Stars: Paul Giamatti, Thomas Haden Church, Virginia Madsen, Sandra Oh
Votes: 204,348 | Gross: $71.50M
25. Ferris Bueller's Day Off (1986)
PG-13 | 103 min | Comedy
A popular high school student, admired by his peers, decides to take a day off from school and goes to extreme lengths to pull it off, to the chagrin of his Dean, who'll do anything to stop him.
Director: John Hughes | Stars: Matthew Broderick, Alan Ruck, Mia Sara, Jeffrey Jones
Votes: 386,631 | Gross: $70.14M
26. Slap Shot (1977)
R | 123 min | Comedy, Drama, Sport
A failing ice hockey team finds success with outrageously violent hockey goonery.
Director: George Roy Hill | Stars: Paul Newman, Michael Ontkean, Strother Martin, Jennifer Warren
Votes: 41,254 | Gross: $28.00M
27. The Wedding Singer (1998)
PG-13 | 97 min | Comedy, Music, Romance
Robbie, a singer, and Julia, a waitress, are both engaged, but to the wrong people. Fortune intervenes to help them discover each other.
Director: Frank Coraci | Stars: Adam Sandler, Drew Barrymore, Christine Taylor, Allen Covert
Votes: 162,371 | Gross: $80.25M
28. Uncle Buck (1989)
PG | 100 min | Comedy
Laid back commitment-phobe Buck babysits his brother's rebellious teenage daughter and her cute younger brother and sister.
Director: John Hughes | Stars: John Candy, Macaulay Culkin, Jean Louisa Kelly, Gaby Hoffmann
Votes: 107,772 | Gross: $66.76M
29. Anchorman: The Legend of Ron Burgundy (2004)
PG-13 | 94 min | Comedy
In the 1970s, an anchorman's stint as San Diego's top-rated newsreader is challenged when an ambitious newswoman becomes his co-anchor.
Director: Adam McKay | Stars: Will Ferrell, Christina Applegate, Steve Carell, Paul Rudd
Votes: 378,694 | Gross: $85.29M
30. Moneyball (2011)
PG-13 | 133 min | Biography, Drama, Sport
Oakland A's general manager Billy Beane's successful attempt to assemble a baseball team on a lean budget by employing computer-generated analysis to acquire new players.
Director: Bennett Miller | Stars: Brad Pitt, Robin Wright, Jonah Hill, Philip Seymour Hoffman
Votes: 464,832 | Gross: $75.61M
31. Borat (2006)
R | 84 min | Comedy
Kazakh TV talking head Borat is dispatched to the United States to report on the greatest country in the world.
Director: Larry Charles | Stars: Sacha Baron Cohen, Ken Davitian, Luenell, Chester
Votes: 442,291 | Gross: $128.51M
32. I Heart Huckabees (2004)
R | 107 min | Comedy
A husband-and-wife team play detective, but not in the traditional sense. Instead, the happy duo helps others solve their existential issues, the kind that keep you up at night, wondering what it all means.
Director: David O. Russell | Stars: Jason Schwartzman, Jude Law, Naomi Watts, Mark Wahlberg
Votes: 66,282 | Gross: $12.78M
33. Funny People (2009)
R | 146 min | Comedy, Drama
When seasoned comedian George Simmons learns of his terminal, inoperable health condition, his desire to form a genuine friendship causes him to take a relatively green performer under his wing as his opening act.
Director: Judd Apatow | Stars: Adam Sandler, Seth Rogen, Leslie Mann, Eric Bana
Votes: 123,643 | Gross: $51.86M
34. Zoolander (2001)
PG-13 | 90 min | Comedy
At the end of his career, a clueless fashion model is brainwashed to kill the Prime Minister of Malaysia.
Director: Ben Stiller | Stars: Ben Stiller, Owen Wilson, Christine Taylor, Will Ferrell
Votes: 292,002 | Gross: $45.17M
35. Christmas Vacation (1989)
PG-13 | 97 min | Comedy
The Griswold family's plans for a big family Christmas predictably turn into a big disaster.
Director: Jeremiah S. Chechik | Stars: Chevy Chase, Beverly D'Angelo, Juliette Lewis, Johnny Galecki
Votes: 220,164 | Gross: $71.32M
36. This Is 40 (2012)
R | 134 min | Comedy, Drama, Romance
Pete and Debbie are both about to turn 40, their kids hate each other, both of their businesses are failing, they're on the verge of losing their house, and their relationship is threatening to fall apart.
Director: Judd Apatow | Stars: Paul Rudd, Leslie Mann, Maude Apatow, Iris Apatow
Votes: 150,504 | Gross: $67.54M
37. Due Date (2010)
R | 95 min | Comedy, Drama
High-strung father-to-be Peter Highman is forced to hitch a ride with aspiring actor Ethan Tremblay on a road trip in order to make it to his child's birth on time.
Director: Todd Phillips | Stars: Robert Downey Jr., Zach Galifianakis, Michelle Monaghan, Jamie Foxx
Votes: 358,024 | Gross: $100.54M
38. Hot Tub Time Machine (2010)
R | 99 min | Comedy, Sci-Fi
A malfunctioning time machine at a ski resort takes a man back to 1986 with his two friends and nephew, where they must relive a fateful night and not change anything to make sure the nephew is born.
Director: Steve Pink | Stars: John Cusack, Rob Corddry, Craig Robinson, Clark Duke
Votes: 186,553 | Gross: $50.29M
39. Sixteen Candles (1984)
PG | 93 min | Comedy, Romance
A girl's "sweet" sixteenth birthday is anything but special: her family forgets about it, and she suffers from every embarrassment possible.
Director: John Hughes | Stars: Molly Ringwald, Anthony Michael Hall, Justin Henry, Michael Schoeffling
Votes: 126,409 | Gross: $23.69M
40. The Hangover Part II (2011)
R | 102 min | Comedy
Two years after the bachelor party in Las Vegas, Phil, Stu, Alan, and Doug jet to Thailand for Stu's wedding. Stu's plan for a subdued pre-wedding brunch, however, goes seriously awry.
Director: Todd Phillips | Stars: Bradley Cooper, Zach Galifianakis, Ed Helms, Justin Bartha
Votes: 534,901 | Gross: $254.46M
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