The 50 Best Comedies of the Past 50 Years: 20-11

20 Better Off Dead (1985)

We’re passing over the more obvious John Hughes choices in the 80s teen movie genre and siding with Savage Steve Holland’s Better Off Dead, a tremendously funny coming-of-age flick bursting with dark comic weirdness.  It’s one of John Cusack’s first shots at carrying an entire comedy on his own and he kills it, with the help of 80s uber-buddy Curtis (Risky Business, Revenge of the Nerds) Armstrong and Diane (The Last American Virgin) Franklin. From Savage Steve’s surreal animations to a malevolent paper boy demanding his two dollars, the movie keeps delighting with comedy surprises. One of those “if you love it, you really love it” gems.

19 Pee Wee’s Big Adventure (1985)

Pee Wee’s Big Adventure caught two unique talents just as they were coming into their own comic superpowers.  First is Pee Wee himself, the supremely odd comedy creation of Groundlings veteran Paul Reubens.  He’s part kiddie show host, part giggling man-child, part creepy ventriloquist dummy come to life -- a fully realized eccentric who comes complete with his own candy-colored universe.  The second talent is Tim Burton, pre-Batman, pre-Beetlejuice, pre-Edward Scissorhands. Moviegoers had never seen anything like the work of this animator-turned-auteur, who waved a wand and made dreamlike cartoons come to life.  Pairing the two unknowns was inspired, creating the funniest story either man has ever put to film. 

18 Team America: World Police (2004)

Subjects satirized in Team America: World Police, a movie in which several characters suspiciously sound like the South Park gang:  Ignorant celebrity activism, Jerry Bruckheimer explosion parties, 1960s puppet show Thunderbirds, military excess, musicals about AIDS, patriotic power ballads, mid-movie sex scenes, and post 9/11 America. The fact that it’s all done with marionettes just makes it funnier. Sure, the Kim Jong-Il accent is offensive but so is pretty much every other scene in the movie - so take your pick. We’ll never see another one of these puppetfests -- manipulating all those strung-up dummies took forever and nearly killed Matt Stone and Trey Parker.  Savor this one because it’s all you’re going to get. 

17 Office Space (1999)

Mike Judge joints are slow burns -- King of the Hill, for example, was never outrageous enough to become a sitcom juggernaut but it was just damn good enough to build an incredibly faithful following.  The same can be said of Office Space, a movie that performed poorly at the box office but has slowly gained momentum into all-timer status ever since. The movie acts as a primal scream response to worker-drone asphyxiation -- who among us hasn’t dreamed of murdering malfunctioning printers, which somehow jam just as much today as they did in 1999? Special shout out to the criminally underrated Gary Cole for creating Bill Lumbergh, the droning, passive-aggressive manager we’ve all had to endure at some point in our working lives. Somebody give him the printer treatment.

16 Rushmore (1998)

Wes Anderson comedies aren’t the all-out guffaw-bots we get from, say, Judd Apatow or the Farrelly brothers. But there’s room for gentler laughers and Rushmore stands as one of Anderson’s best.  Jason Schwartzman as Max Fischer and Bill Murray as Herman Blume make an electric pair, with young Max’s unwarranted optimism providing a comic counterweight to Blume’s maniacal despair. In a just world, Murray would have won an Oscar for this one.  The biggest laughs come from Max’s hyper-involvement in Rushmore Academy’s extracurriculars, including calligraphy club president, astronomy society founder, and fencing team captain. And let’s not forget his theatrical staging of Serpico. 

15 Monty Python and the Holy Grail (1975)

It’s a small miracle that Holy Grail has aged as well as it has. Part of that is due to the film’s medieval setting, making the jokes more timeless than other comedies produced in the 1970s. But that’s selling the Python crew short -- Holy Grail is simply full of damn funny scenes. It was the group’s first movie with a cohesive story (And Now For Something Completely Different, also hilarious, was a compilation of Python comedy sketches), and regularly shows up on lists of the funniest movies of all time.  Holy Grail is also the only movie on this list to inspire a Tony Award-winning Broadway musical in Spamalot. Way to leverage the IP, guys.

14 There’s Something About Mary (1998)

Peak Farrelly Brothers!  The sibling filmmakers have always had a flair for the stupid (Dumb and Dumber) and the gleefully offensive (Shallow Hal), but the combination never worked as well in a cohesive story as it does here. It’s not a surprise that Ben Stiller and Chris Elliott are hilarious, but who knew about the untapped comic potential of Cameron Diaz and Matt Dillon? There’s Something About Mary ranks near the top of our list in terms of pure belly-laughs-per-minute, a comic gut punch that doubled over audiences. The film’s biggest scenes are so etched in our comedy brains -- the hair-gel, the zipper -- that shorthand nicknames are all we need to start laughing again.  

13 Borat! Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan (2006)

Sacha Baron Cohen’s ingenious conceit with Borat was creating a foreign character capable of the most offensive behavior imaginable -- but forgivable given his perceived cultural ignorance.  Ironically, the (fictional) strange social practices of Kazakhstan ended up shining a spotlight on the even stranger cultural mores of America. High five to Cohen for remembering to be ridiculously silly amidst all the societal commentary.  Given the omnipresence of Borat after the film’s release, another guerilla endeavor seemed impossible. That Cohen pulled it off again with Borat Subsequent Moviefilm is a stunner.

12 Animal House (1978)

Animal House is the movie that invented the comedy blockbuster, exploding not just as a hit but as an out-and-out phenomenon.  It’s hard to overstate the impact it had on youth culture in 1978--how many other flicks on this list ended up on the cover of Newsweek?  Humor mag The National Lampoon had already made its imprint on television with Saturday Night Live, but network restraints only allowed its shock-humor to go so far.  Animal House, written by several Lampoon alums, took those anarchic sensibilities to an entirely different level. A blueprint for so many slobs-against-snobs movies to come, including The Blues Brothers, Caddyshack, and Stripes.  Oh yeah, it’s also the film that made John Belushi a movie star.  

11 Bridesmaids (2011)

We shouldn’t have had to wait until 2011 to have a killer comedy headlined by an all-female cast but here we are.  That Bridesmaids shows up so high on this list proves that it’s more than a participation trophy for gender representation. Kristen Wiig made good on her SNL promise by playing a lead who was the ‘sane’ center of the action as well as a complete neurotic mess. The entire cast, from Maya Rudolph and Rose Byrne to Ellie Kemper and Wendi McClendon-Covey, knocks it out of the park.  But it was Melissa McCarthy in her Oscar-nominated turn as Megan who kicked the movie into another solar system, becoming a comedy movie superstar in the process. Let’s all sneak off to the airplane restroom and celebrate. 

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

50 Best Comedy Movies of the Past 50 Years, 30-21

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