10 Hilarious Comedy Films To Learn From - Raindance

“Dying is easy, comedy is hard.” It’s one of those phrases that have been heard and repeated so many times that there’s really no way of knowing who coined it first. Yet we all know that it holds some truth. For those of us who want to write/direct/produce films, we know that great comedy -or even good comedy- is an incredibly hard feat to achieve. If you’re like me and can’t wait to be on Steve Kaplan’s comedy course here are 10 great comedy films you can/should/must draw inspiration from until then.

10) Wag The Dog

I can hear you screaming already: as political satires go, Kubrick’s “Dr. Strangelove” is the go-to film. Forgive me, film deity, for I have sinned and can’t be drawn into any of Kubrick’s films. (Rest assured that I pray for my film redemption every day.) However, having recently discovered this Barry Levinson film I thought it must find its way into this list.

Starring Robert De Niro and Dustin Hoffman as a spin-doctor hired to divert the public’s attention from the US president’s sex scandal (that was only a few months before Bill Clinton’s own real life sex scandal), and a Hollywood producer enlisted to provide images of a fake new war, this film reaches levels of cynicism that “House of Cards” barely tops. David Mamet’s talky script goes for the laughs, though, and provides them by the sheer outlandishness of the situation, the characters’ knowledge that the only way for their endeavor to work is to go further and further and through Dustin Hoffman’s passionate Hollywood producer character. Robert De Niro’s low-key spin doctor works equally well and watching these two iconic actors play off each other is one of the joys of this film -when you’re not too busy being sucked into the story.

9) Groundhog Day

Do you ever find yourself thinking, a few hours after a given conversation, “I should have said this instead of that!” Given the opportunity, would you do things differently? Bill Murray was given the opportunity to relive the same day again -and again, and again…- and eventually had a perfect day. Now that doesn’t sound so bad, but if you’re a jaded, misanthropic man whose job assignment is tedious enough that you don’t even want to do it once -then you’ve got comedy. Bill Murray’s character gets plenty of time to learn from his mistakes, and eventually has the perfect day by opening up to the world around him, helping people -and he eventually gets the girl (I should have said spoiler alert).

8) Bridesmaids

In a world where “The Hangover”-type films are on top of the box-office, an unexpected antihero came to the rescue. (You’re more than welcome to re-read that sentence with the classic blockbuster trailer voice.) The surprise hit of the summer of 2011 was the brain child of Saturday Night Live alum Kristen Wiig (who’s since made a string of touching indie films). It was high time that women got their raunchy comedy and she provided it.

Wiig’s Annie is the Maid of Honor at her best friend’s wedding, so she’s in charge of putting together the bachelorette party. She already has a hard time holding her life together, and the unexpected list of seemingly unsurmountable tasks puts her on the brink of falling apart. She has to manage her best friend’s friends who are invited to the party -and they’re quite the set of characters.

By subverting expectations of this being a “girly” film, providing laughs from a set of distinctive characters -notably Melissa McCarthy’s, who made her breakout film performance and deservedly got nominated for a Best Supporting Actress Oscar- and going further into outlandishness without it feeling pushy, Wiig’s script, which was helmed by Paul Feig under Judd Apatow’s watchful producing, created a millennial classic.

7) When Harry Met Sally

“I try to write parts for women that are as complicated and interesting as women actually are.” Nora Ephron said. As she asked the age-old question of whether men and women can be platonic friends, she definitely did that.

Gender is a core part of our identity, and the complex playfulness between men and women is an endless well of ideas for writers since the dawn of humanity. Exploring contemporary social mores and finding characters’ strength and flaws in them, she wrote an engaging, fresh and hilarious story about two friends who eventually overcome doubt (about themselves and each other) and end up together.

Oh and that deli scene?


6) Good Morning Vietnam

When Robin Williams tragically passed away, the world was quick to remember the vivid brokenness and humanity he provided to his characters, in such memorable films as “Good Will Hunting” and “Dead Poets Society”. He was also remembered for his infinite ability to be hilarious, as he was when he provided the voice of the Genie in “Aladdin”.

Both sides were shown in one of his earlier films: “Good Morning Vietnam”. As a provocative and irreverent DJ assigned to military radio during the Vietnam War, facing the stern authority of his hierarchy while finding growing popularity with the troops, Williams showed the struggle of hope and lightness in the face of the horrific reality of war. He famously improvised all his character’s lines when he was one the air.

Williams provided the same comic relief for his friend Steven Spielberg during the shooting of “Schindler’s List”: after a day’s shoot they would be on the phone for hours just so that the director could think about something else.

When you get an actor with such an innate ability for comedy, play to their strengths.

5) The Producers

Mel Brooks is one of the funniest people to have walked this earth, and that was apparent even before his directing debut, as half of the comedy duo he formed with Carl Reiner. When “The Producers” landed, no one quite knew what to make of it -no one had thought of doing jokes about Nazis and, to be fair, they don’t come across as the most obvious subject for comedy.

Brooks brought together contrasting characters: the outlandish, down-on-his-luck producer played by Zero Mostel, and the uptight accountant played by Gene Wilder, and had them bound in the scheme to produce a flop as “a producer could make more money with a flop than he could with a hit”.

The odd couple chemistry of the characters paired with the almost caricatural people they encounter makes for a hilarious ride all the way to a touching ending. For instance, the sight of Gene Wilder’s uptight Leo Bloom frozen in fear in the camp dream that is Roger De Bris’ house is comedy gold.

It has since become a classic film, which was remade into a musical, and a film adaptation of said musical -neither of which really distance themselves from the original material (which is both to their credit and to their lack of novelty). Brooks won the Best Writing Oscar (facing staunch competition from Kubrick’s “2001”, and “The Battle of Algiers”).

4) A Fish Called Wanda

This is the only film in history that has actually made someone die laughing, understandably so as it is extremely well-written, directed with enough efficiency to carry the narrative and provide laughs without getting in the way of the story, and cast with brilliant actors.

What are the ingredients, you ask? Virtually every character is riddled with hilarious idiosyncrasies, and everyone seems to set up, double cross or manipulate someone else in some way.

3) Tootsie

Tootsie was Dustin Hoffman’s passion project for years. He plays Michael Dorsey, an actor so stubborn about his character that no one will hire him. So what would anyone do? He can’t get a job as an actor, so maybe he will as an actress. And he does, and he becomes America’s new star of daytime soap.

Many jokes come from the character’s point of view as a man shifting toward that of a woman, and the sexism he endures, as well as the mess he gets in with his friends and his co-worker (Jessica Lange) who is Dorothy’s friend but who Michael falls for.

By getting deeper and deeper into his character, and the situation he has to be growingly inventive to escape awkward situations, thus providing incredible laughs.

2) Annie Hall

Woody Allen is peerless. He’s been writing and directing a film a year for five decades. He’s drawn inspiration from Ingmar Bergman, Federico Fellini and masters of European arthouse cinema, yet his films have become a genre of their own. His landmark 1977 film was both heartfelt and hilarious and marked a turning point in his career, as he shifted from the “early funny ones” to another level of maturity and character exploration.

And characters are where the laughs come from: neurotic people finding each other, equally broken yet in different ways, needing each other yet having to be apart, each with contrasting worldviews: sparks fly.

Jokes fly too, from Woody Allen’s wisecracking comedy writer Alvy Singer as well as from Diane Keaton’s witty, eponymous character. The film was reportedly drawn from their real-life relationship. Despite the criticism that they’re both playing themselves, rarely have too actors played so beautifully, sensitively and hilariously off each other.

1) Some Like It Hot

Billy Wilder is one of the most influential filmmakers of the 20th century. He’s a writer first, knows how to do exposition without giving too much away, and knows how to tie up a story, put a bow around it and deliver it with the fireworks.

This 1959 classic follows two jazz musicians (Tony Curtis and Jack Lemmon) who disguise themselves in drag and enroll in an all-female band to flee mobsters. The setup is simple, there three acts are there (and spiced up), the dialogue is snappy and you can’t stop laughing. The jokes come from the confusion on the character’s gender identities (sometimes even the characters are confused).

As they get entangled deeper into relationships both as males and as their female alter egos, laughs just keep coming all the way to the final line. By exploring the various pairings, Wilder milks his material to the fullest, keeps it under control and brings it home with flying colours.

That’s it?

These are just ten comedy films out of many more that could have made this list? Are there unforgivable ones missing? Let me know in the comments or by tweeting at me!



Baptiste is a writer hailing from the part of France where it is always sunny. After a stint in politics and earning his Master's Degree in Management, he was a marketing intern for the 23rd Raindance Film Festival in 2015, then joined the team permanently in 2016 as the Registrar of the MA in Filmmaking. He is passionate about diversity in film, which he researches and writes about extensively. He is the producer of the hit webseries "Netflix & Kill" and the multi-award-winning short film "Alder", as well as a writer for stage and screen. His short film "U Up?" is currently in pre-production.