Moving Write Along: Advice from the Experts – The Top 10 Comedy Movies
by Steve Kaplan,

Sometimes at the end of one of my workshops or seminars, I’m asked, “What’s your favorite 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 favorite,” 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 epitomize what’s greatest in comedy writing, performance and filmmaking. (Some of you might notice that I still have more then 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. Ever. And let’s not forget about 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.

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.

Bowfinger. 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 Honorable 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 Hope and Bing Crosby 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 Chaplin 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 humor 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 …

The 40-Year-Old Virgin. Judd Apatow’s brilliant melding of raunchy humor 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 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. Post your favorites below. And you know what? You’re right too. Let’s watch ‘em all!

For more than 15 years, Steve Kaplan has been the industry’s most sought-after expert on comedy writing and production. In addition to having taught at UCLA, NYU, Yale and other top universities, Steve Kaplan created the HBO Workspace, the HBO New Writers Program,  and was co-founder and Artistic Director of Manhattan’s Punch Line Theatre. His Comedy Intensive seminar has been presented around the world, and Kaplan has served as a consultant to such Screen Australia and the New Zealand Film commission, as well as companies such as Dreamworks, Disney, HBO and others. Follow Steve on Twitter.

LA Writers, join Steve for a Free Comedy Workshop tonight, September 23, from 6:30 – 9 pm at the Showbiz Store and Cafe LA, 500 S. Sepulveda Blvd., Los Angeles, CA 90049. Register here:


Comments are closed.

  1. Me 12 years ago

    I don’t think you should leave Tootsie out. I’d swap all Woody Allen comedies for that one. It’s such a classic, and so brilliant on so many levels. And I’d have chosen The Court Jester over The 40-year Old Virgin, but maybe that’s because I’m a woman. 😉

  2. mitch mcguire 12 years ago

    Steve you forgot Hail The Conquering Hero and Miracle Of Morgan’s Creek, or any of Sturges’ films, but that may be due to your young age, but you did include a Road picture, so you know about the era, you just got it…well not wrong, cause we’re talking personal choices here. But I would not chose any of the Road pix…too corny. No Marx Bros?! No Billy Wilder?! No Jerry Lewis? haha.

  3. […] Today, on Write On! Online, comedy expert Steve Kaplan lists his Top Comedy Films. […]

  4. Greg Vovos 12 years ago

    Great list, Steve.

    I love TOMMYBOY. And not just because I love Chris Farley (RIP), but I love the heart of this movie. And the scene with the paintings of all the companies past presidents on the wall that ends with Tommyboy standing at a dutch door is comedy gold, as are many others in that movie.

    And my first favorite comedy ever…CADDYSHACK. Spalding will have nothing and like it.

  5. Steve Kaplan 12 years ago

    Mitch, the Sturges film that’s my favorite is Sullivan’s Travels. Wilder’s is The Apartment. You’re right–they shouldn’t be left off the list. (Except maybe Jerry Lewis). A real list of best comedies would run 30, 40, 50 or more. They were all great (except maybe Jerry Lewis). 😉

  6. […] Expert Columns: Steve On Screenwriting: Understanding Drama by Steve Kaire Top Comedy Movies by Steve Kaplan, Top Ten Lists by Tony Hastings, The Top Ten […]


We're not around right now. But you can send us an email and we'll get back to you, ASAP. Thanks!


Copyright © 2020 Debra Eckerling, Write On Online, All Rights Reserved.

Log in with your credentials

Forgot your details?