The Funniest Movies Ever

Picking the chosen few is a fool’s errand, which we suppose is appropriate for April 1

Before you write your congressman because your favorite movie was left out, know that this was a nearly impossible task. Dozens of classics could’ve wound up on this esteemed list, including but not limited to: The Jerk, Pee-Wee’s Big Adventure, The Party, Some Like it Hot, Knocked Up, There’s Something About Mary, A Fish Called Wanda, Trading Places, Modern Times, This Is Spinal Tap, Waiting for Guffman, The Naked Gun!, Step Brothers, Walk Hard, Big, Sleeper, The Odd Couple, The Out of Towners, The Hangover, Office Space, Fast Times at Ridgemont High, Animal House and, of course, Bringing Up Baby. By our count we’ve mentioned about 23 titles in the intro alone, so grab a quarter-ton of popcorn, a few cases of No Doz and get to watchin’!

“It’s just a flesh wound.” Monty Python and The Holy Grail (1975). Controversy will erupt over our snub of The Life of Brian and The Meaning of Life. Still, we’re confident in our selection. From the Knights Who Say Nee, to a French soldier farting “in our general direction,” this is Python wit at its best.

“We got no food. No Jobs. Our pets’ heads are falling off!” Dumb & Dumber (1994). Many would place There’s Something About Mary in this spot. Dumber gets the nod because it’s the Farrellys’ first feature. The Rhode Island brothers would own film comedy for the remainder of the ’90s with their particular brand of exaggerated, gross-out humor. None of it would have been possible without Harry and Lloyd’s cross-country romp.

“I have been touched by your kids … and I’m pretty sure that I’ve touched them.” School of Rock (2003). Jack Black is at his maniacal best in this instant classic, directed by the traditionally “indie” Richard Linklater. Black kills as Dewey Finn, a wannabe rock star who turn his students into a makeshift rock group.

“Know how I know you’re gay?” The 40-Year-Old Virgin (2005). With Judd Apatow’s directorial debut and Steve Carell’s first starring role, magic happened. A simple enough set-up: A nerdy man approaching middle age who has never done the deed gets the help of a single mom and his co-workers (Apatow faves Paul Rudd and Seth Rogen).

“Or perhaps you don’t want to see the second largest ball of twine on the face of the Earth?” Vacation (1983). The exploits of the Griswolds are the stuff of legend. In this road-trip comedy, Chevy Chase was on top of the world, flirting with Christie Brinkley, strapping corpses to the roof of the station wagon, and shooting John Candy in the keister with a pellet gun.

“I was a heroin addict. Now I’m a methadone addict.” Annie Hall (1977). A Best Picture rom-com for The New Yorker subscribers. Woody Allen is a neurotic comedian (more or less himself) trying to date a flighty, free spirit (Diane Keaton, more or less herself). Who can forget Allen sneezing a pile of cocaine across a room? Or Annie’s psychotic brother (a young Christopher Walken) confessing his urge to drive into oncoming traffic?

“A guy like that, you just sit back and say, ‘OK, I’ll never get there.’” – Jim Carrey The General (1926). Buster Keaton starred in and co-directed this funny-as-hell silent-era masterpiece. Buster stars as Johnny Gray, a bumbling Southerner who, despite being shunned by the Confederate Army, winds up single-handedly battling Union saboteurs.

“Candygram for Mongo.” Blazing Saddles (1974). Standing one urinal over from Mel Brooks was one of the highlights of this writer’s life. Brooks swings for the fences in his Western spoof starring Cleavon Little, Gene Wilder and Madeline Kahn. Mel’s secret screenplay weapon? A young Sanford and Son staff writer named Richard Pryor.

“By the way, is there anyone on board who knows how to fly a plane?” Airplane! (1980). The greatest spoof of all time features Leslie Nielsen, Robert Hays and the late Peter Graves. Even Kareem Abdul-Jabaar gets his share of laughs in this madcap tale of a flight in distress. The creative team had previously done The Kentucky Fried Movie and would go on to make Top Secret!, Ruthless People, and The Naked Gun!. But only Airplane! had America speaking Jive for a decade.

“You got a .45 revolver that holds six bullets. I counted at least 20 shots …” I’m Gonna Git You Sucka (1988) This Blaxploitation parody debuted the Wayans brothers. Keenan Ivory Wayans stars as a veteran who returns to his old neighborhood. This film doesn’t miss a gag: from a gold chain overdose to a pimp with fish tanks for shoes.

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