The Funniest Movies Over The Past 30 Years

1
1985: Clue
A wacky, macabre farce that manages upbeat energy despite nonstop homicide.
2
1986: Little Shop of Horrors
The first of two musicals on the list, and a rare case of a remake that far surpasses the quality of its source material.
3
1987: Planes, Trains and Automobiles
The best version of Steve Martin (uptight and unfortunate) stuck beside the best version of John Candy (chipper, oblivious, and accident-prone) on one long journey.
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4
1988: The Naked Gun - From the Files of Police Squad!
Just a few steps below the masterpiece that is 1980's 'Airplane!', this screwball Leslie Nielsen comedy is merciless in its devotion to silliness.
5
1989: Crimes and Misdemeanors
Though not as wacky or far out as Woody Allen's early comedies, this entry manages a terrific satiric tone.
6
1990: Home Alone
Kicking off a string of "youthful" comedies that would build the identity of the 1990s is the mother of them all: a slapstick cat and mouse game that charmed a generation.
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7
1991: Barton Fink
The darker of two Coen Bros entries on this list, and probably the weirder... but in no small way just as funny as anything else they've done.
8
1992: My Cousin Vinny
A clash of cultures results in a sweet, wholesome (other than the language) comedic underdog story that does wonders with the Joe Pesci persona.
9
1993: Groundhog Day
Often considered Bill Murray's best role, the introspective 'Twilight Zone' premise is played just as much for laughs as it is for philosophical meanderings.
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10
1994: Dumb & Dumber
It lives up to its title all right, but you can't deny the simple pleasures of idiotic puns or Jim Carrey's physical acumen.
11
1995: Clueless
The very best high school comedy ever put to film (sorry, John Hughes) is clever, sensitive, wry, and one of the most quotable movies of its decade.
12
1996: The Birdcage
Though Robin Williams keeps himself unusually tempered in this film, he and screen partner Nathan Lane still manage some big, vivacious laughter.
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13
1997: Liar Liar
This list's second turn for Carrey would kick off a bad habit of "cursed with a one-note conflict" films ('Bruce Almighty,' 'Yes Man,' 'Mr. Popper's Penguins'), but man was he a riot with that pen.
14
1998: The Big Lebowski
Coen flick No. 2 is for sure the most frequently referenced of their works (especially by those residing in dorm halls), and is likely their "lightest" work... deaths and crime capers aside.
15
1999: South Park: Bigger, Longer & Uncut
Yes, it's a broad, crass, crudely animated TV show spinoff... but the brilliant Sondheim-approved musical is meticulously constructed (and with some of the catchiest tunes imaginable).
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16
2000: Best in Show
Christopher Guest's funniest flick to date gets the best out of every member of his usual team (Eugene Levy, Jane Lynch, Michael McKean, Parker Posey), with the bonus of cute dogs.
17
2001: Wet Hot American Summer
Halfway through watching this would-be '80s throwback, you realize that it actually might be the most ingenious, irreverent, anarchic parody ever created.
18
2002: Orange County
It's silly, snoozy, and drenched in millennial mentalities, but the Colin Hanks/Jack Black flick is loads of good natured, surprisingly clever fun.
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19
2003: School of Rock
Two Jack Black movies in a row might elicit a scoff... but would it help to remind you that this one was directed by 'Boyhood' helmer Richard Linklater?
20
2004: Shaun of the Dead
Edgar Wright crafted something new and wonderful with his zombie movie parody 'Shaun of the Dead,' which he mimicked but never quite reproduced in his Cornetto films to follow.
21
2005: The 40-Year-Old Virgin
Judd Apatow's feature debut lacks the guttural drama of his films to come... and is all the more enchanting because of it. How a film so brazenly about sex managed to stay this sweet is miraculous.
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22
2006: Idiocracy
An unappreciated wonder from Mike Judge (it's superior even to 'Office Space,' if you can believe that) does indeed go blue... but it knows what makes for good satire.
23
2007: Superbad
Teen male friendship was never depicted with such vulnerability, nor with such wackiness, as in Greg Mottola's high school comedy of errors.
24
2008: Role Models
David Wain's second entry on the list is a far more "by the book" film than 'Wet Hot,' but still manages that goofy, often scathing charm.
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25
2009: Inglourious Basterds
Though comedy is not its premiere intent, Tarantino's Nazi hunting flick is a laugh riot thanks to Brad Pitt and Christoph Waltz.
26
2010: Scott Pilgrim vs. the World
Although Wright might not have made the 'Shaun' magic with 'Hot Fuzz' or 'The World's End,' he did something spectacularly enjoyable with 'Scott Pilgrim,' and will remain in fans' favor eternally.
27
2011: Conan O'Brien Can't Stop
The only documentary on the list earns that distinction for good reason. The comic genius that is Conan O'Brien is depicted as such here, but also showcases his harrowing obsession with comedy.
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28
2012: Holy Motors
The weird, little seen, totally surreal picture might come off as "heady," but totally earns laughter with its venturing into the strangest corners of our imaginations.
29
2013: Computer Chess
Perfecting the mockumentary style and the "awkward humor" gambit, 'Computer Chess' delivers hilariously derisible characters and oddball situations.
30
2014 (So Far): The Grand Budapest Hotel
We can't imagine a 2014 movie that would be funnier, flightier, and more filled with whimsy than Wes Anderson's 'Grand Budapest' ... but we're holding out!

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