The Best Comedy Movies of the Past 50 Years: 30-21

Rodney Dangerfield, Wayne Campbell, and Ron Burgandy vie for comedy supremacy.
The Best Comedy Movies of the Past 50 Years: 30-21

In our last comedy movie countdown, Adam Sandler, Napoleon Dynamite, and the Dude battled it out for laugh supremacy.  As we get closer to number one, where does your favorite rank?  

Back to School (1986)

It’s another edition of slobs vs. snobs, but in this case, the disrespected Rodney Dangerfield is both -- the uneducated slob who somehow got rich anyway.  When his son threatens to drop out of school, Rodney decides to drop in -- and the stodgy old dean isn’t going to like his party antics!  Dangerfield is one of the oddest success stories in comedy, never really making it big with his “I don’t get no respect” schtick until younger audiences discovered him when he was nearly 60.  Back to School captures that funky dynamic, with Rodney and undergrads whooping it up in the hot tub. Seems like a good way to spend one's golden years.

Wayne’s World (1992)

Still the highest-grossing Saturday Night Live film of all time, Wayne’s World launched the comedy movie career of Mike Myers. While some of his go-to bits became formulaic over the course of too many Austin Powers movies -- the winking asides through the fourth wall, the movie-in-a-movie pop-culture parodies,  and the endless repetition of catchphrases -- it’s all first-time fresh here as Myers throws hundreds of jokes at the screen to see what sticks.  Schwing!  Wayne’s World also gave new life to Queen’s Bohemian Rhapsody, which, depending on how you feel about the song, was a triumph or tragedy.

Naked Gun: From the Files of Police Squad! (1988)

Now here’s something you don’t see every day -- a failed TV sitcom that becomes an iconic comedy movie franchise.  Fresh off the success of Airplane!, creators Zucker, Abrahams, and Zucker took their 100-jokes-a-minute approach to cop shows on the small screen. That show, Police Squad!, was canceled after only four episodes.  Despite its status as a gone-too-soon critical darling, it still seemed an odd candidate for the big-screen treatment.  And yet here we are, with a movie that Empire ranked as the 7th funniest comedy of all time. Laugh for laugh, you could argue that Naked Gun deserves to be even higher -- the film never stops dealing out gags, with way more hits than misses.  There are probably better movies but for sheer gut-busting, Naked Gun is an all-timer.

The Princess Bride (1987)

The Princess Bride works both as a straight-up fairy tale and an out-and-out farce, with its goofy comedy bits livening up an old-fashioned love story. There’s a Monty-Python-meets-Mel-Brooks vibe, no doubt brought about by its killer comedy cast, including Christopher Guest, Billy Crystal, Wallace Shawn, Peter Cook, and Carol Kane. Brooks would have been an interesting directing choice, but Rob Reiner, the son of Mel's old partner Carl, goes for laughs that are more subtle, delivered with a wry smile rather than a shout and a rimshot. Maybe the best comic performance comes from dramatic actor Mandy Patinkin, avenging his father with a line you can probably recite by heart. Finally, a raucous shout out to Andre the Giant, winning the category of All-Time Best Comic Performance by a 7’4” Wrestler.

Booksmart (2019)

It’s tempting to call Booksmart Superbad for girls,” which is both a compliment and a backhanded slap to the face.  It’s true -- both stories feature introverted best friends who are teetering on the verge of adulthood and the potential loss of said friendship.  But Booksmart is far from a cookie-cutter imitation. Set only a decade after Superbad, Booksmart seems to take place in a different world, one where shifting sexual orientations and gender designations are a simple fact of life.  The movie introduces a whole set of high school archetypes who are instantly familiar yet somehow new to the big screen. Did we mention it's hilarious?  We should because that’s the most important part.

Big (1988)

There have been a ton of “switching age” comedies -- 17 Again, 13 Going on 30, Peggy Sue Got Married, heck, even Shazam.   But Big has something the rest of them don’t:  Tom Hanks.  He was already a comedy star before Big, but like his contemporaries Bill Murray and Michael Keaton, he spent his early movie days as a motor-mouthed party animal who thumbed his nose at The Man.  Big took Hanks from comedy actor to actor-actor, garnering his first Academy Award nomination and forever changing the kinds of roles he’d be offered.  If there’s no Big, there’s no League of their Own, no Forrest Gump, and definitely no Saving Private Ryan. But to get those dramatic roles?  He had to prove here that he was really, really funny.

Anchorman: The Legend of Ron Burgandy (2004)

Gather up the world’s funniest actors at the peak of their improvisational powers, sketch out an outline of a story, and let those sons of bitches go to town. That’s Anchorman, a flick that allowed Will Ferrell, Paul Rudd, Steve Carell, Christina Applegate, and David Koechner to goof around until we peed our pants. In fact, Anchorman had so many funny alt-takes in the can that Ferrell and director/co-writer Adam McKay released a second version of the same movie, Wake Up Ron Burgandy: The Lost Movie "He is my favorite character I've played, if I have to choose one,” says Ferrell. “Looking back, that makes it the most satisfying thing I've ever done."  You stay classy, San Diego.

Ghostbusters (1984)

For better or worse, Ghostbusters ushered in the age of the special-effects comedy.  Worse because sometimes you get a Land of the Lost or Adventures of Pluto Nash, which seem to confuse explosions and dinosaurs with, you know, comedy.  Better because when you combine amazing special effects with funny actors and a whipsmart script, you get something spectacular. There has never been a better vehicle for Dan Aykroyd’s wonkish sensibilities, and Rick Moranis shined in one of his first big-screen roles. As for Bill Murray? Well, he jet-propelled the movie -- and his career -- into the stratosphere.  Or to put it in Ghostbusters terms, he came, he saw, and he kicked some ass.

Defending Your Life (1991)

Defending Your Life is Albert Brooks’s most satisfying movie, a gem that delivers the satirical shotgun blasts of Real Life and Lost in America with the genuine emotion of … well, nothing he’d ever done before.  It probably doesn’t hurt to have Meryl Streep along for the ride, in one of the warmest, funniest roles of her career. You might not remember, but Rip Torn shows up as well in full Larry Sanders Artie mode, the smarmy Judgment City lawyer who somehow becomes convinced that the cowardly Brooks deserves a place in the afterlife. Heavenly.

Waiting for Guffman (1996)

Waiting for Guffman was the culmination of a lot of things -- the improvised character shenanigans of the National Lampoon Radio Hour, the satirical promise of This is Spinal Tap, and the gentle show-business satire of SCTV.  And it was also the beginning of the Guest mockumentary movement, generating such gems as Best in Show and A Mighty Wind.  But this is where it all started, sweet and simple, and in that simplicity, it might be the best of the lot. The laughs are plentiful, both from tragically misguided theatrics and awkward silences.  If you haven’t seen it, hitch up your panties and run to the nearest streamer. The people of Blaine, Missouri do indeed have talent. 

For more of the best comedy movies, be sure to check out:

50 Best Comedy Movies of the Past 50 Years, 50-41

50 Best Comedy Movies of the Past 50 Years, 40-31

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