Steve Kaplan's top 10 comedy films - Raindance

Sometimes at the end of one of my workshops or seminars, I’m asked, “What’s your favourite comedy?” I find that an almost impossible question to answer. How can I select just one? I love comedy, I love comedians, I love great writing—there are literally dozens I can watch and enjoy over and over again.

So I don’t bother saying, “This one’s my favourite,” or “This one’s the funniest.” Because like potato chips, you can’t pick just one. Or even ten. But I can think of a list of great comic artists and ask myself, “Which one’s the best Road movie, or best Woody Allen, or best Python?” And so here’s my list of ‘IF YOU CAN ONLY SEE ONE ___________ MOVIE, THE ONE YOU SHOULD SEE IS________!”

These might not even be the funniest, but they are the ones which I think most epitomise what’s greatest in comedy writing, performance and filmmaking. (Some of you might notice that I still have more than ten. What can I say? Math was never my strong suit.)

In no particular order:

Groundhog Day

A delicious premise, great supporting cast, and the best Bill Murray performance until St. Vincent. And let’s not forget about the late, great Harold Ramis’ brave direction. He helped give the movie heart, and when he refused to cut the “Old Man Dying” sequence, gave it soul as well.

The Grand Budapest Hotel

Some people feel that Wes Anderson is an acquired taste. Well, acquire it, already! This stylish, deceptively thoughtful confection features a star-studded panoply of great comic performances: Ralph Fiennes, Harvey Keitel, Adrian Brody, Willem Defoe, Edward Norton, Jeff Goldblum. What starts as a light, delicious fairy tale evolves into an intricate, multi-layered, bittersweet romance of love lost and found and a world found and lost. And the best score of the year.

Sleeper/Annie Hall/Manhattan

OK, I couldn’t narrow it down to just one Woody Allen, but these three stand out above all the rest. Annie Hall and Manhattan broke new ground and often broke our hearts, while Sleeper just split our sides. Classic moment: Woody and the giant bag of cocaine.


Yes, Bowfinger. Maybe not as funny as The Jerk or as romantic as L.A. Story or Roxanne, but in its own way it was the ultimate romantic comedy: a daffy valentine to actors, writers, directors, producers, and anyone who ever aspired to any of those roles. That being said, an honourable mention has to go to Waiting for Guffman.

The Producers

Forget the film of the musical. This is prime, rude and funny Mel Brooks, with a pitch-perfect performance by Gene Wilder and the gargantuan talent of the late, great Zero Mostel. Best moment: as the chorus belts out, “Springtime for Hitler,” the camera pans an audience full of slack-jawed New Yorkers, frozen in horror and disbelief.

Road to Utopia

Who doesn’t love Bob and Bing and the Road movies? Utopia finds our boys in Alaska (how prescient) and is full talking bears, talking fish, and the best sight gags, ad-libs and asides of the series. That sound you hear is the fourth wall being constantly broken, as our lovable rogues seem to talk to us more than they do the other characters.

Modern Times

Charlie and the age of Industry, as he is literally swallowed by the assembly line and spit out, a bit worse for wear but still full of pluck and hope.

There’s Something About Mary

The Farrellys’ best. In this film, they navigate the line of gross-out humour and bad taste without crossing over (much). Most memorable scene: some say it’s Cameron Diaz’ hair ‘gel,’ but I vote for Ben Stiller in braces, zipping up while the “frank and beans” are still out. In a bathroom that begins to echo the famous Marx Bros. stateroom scene, the Farrellys reached comic heights as most men in the audience reach for their . . . uh . . . And you might say that this film led to…

40 Year Old Virgin

Judd Apatow’s brilliant melding of raunchy humour with heartfelt character comedy. And the film works because we’re always made to care for Steve Carrell’s arrested adolescent adult, as opposed to simply mocking him. And when he and Catherine Keener finally do the deed, what more of a perfect ending could there be then the entire cast singing and dancing to “Aquarius!”

Monty Python and the Life of Brian

More than a brilliant series of sketches, Brian is a brilliant, complete film, with a coda that captures in a song the entire meaning of comedy and meaning of life.

OK, so that’s ten, but already I’m despondent over the exclusion of James Brooks’ masterful, funny and touching Broadcast News; Ben Stiller’s acid love letter to the Industry, Tropic Thunder; Danny Kaye’s The Court Jester: (Kaye: “But did you put the pellet with the poison in the vessel with the pestle?” Mildred Natwick: “No! The pellet with the poison’s in the flagon with the dragon! The vessel with the pestle has the brew that is true!”); Hugh Grant in the best romantic comedy between a grown man and a boy, About a Boy. . . .

And talking about romantic comedies, how the hell could I forget to include When Harry Met Sally? Or Big? Or Tootsie?

So, you see, the list goes on. You probably have a completely different list of 10. And you know what? You’re right too. Let’s watch ‘em all!

Find out more about Steve Kaplan’s Comedy Screenplay Intensive masterclass



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