Although humor is subjective, some comedy movies are so great that everyone seems to agree they’re hilarious. When they work and the jokes land, comedies can be among the greatest movies of all time. From Mel Brooks to Monty Python to the Zucker brothers, the best comedy filmmakers have mastered both the comedy side and the medium, making sure their movies are well-staged and well-shot in addition to having plenty of laughs.
Comedy is one of the most hit-and-miss genres, but the ones that hit really hit. There are some comedies from more than 50 years ago that still hold up today, like Dr. Strangelove and Some Like It Hot. Some comedies from the 21st century, like Bridesmaids and Shaun of the Dead, are so great that they rank alongside the all-time greats, which include not only the pitch-perfect Back to the Future but also the presciently self-aware Monty Python and the Holy Grail.
20
Step Brothers (2008)
Cruelly under-rated by critics on release, Adam McKay’s delightfully silly comedy Step Brothers is one of Will Ferrell’s funniest movies. Combining with John C Reilly in a partnership that would prove to be surprisingly prolific, Ferrell plays Brennan, a 40-year-old manchild forced to face the prospect of a step-brother (Reilly’s Dale) infringing on his cozy only child set-up when his mother (Mary Steenburgen) remarries.
What follows is a 98-minute war between the two developmentally stunted enemies whose escalation memorably includes scrotal defilement of a drum kit. Infinitely quotable and hugely funny, Step Brothers is easy watching with a slapstick kicker that gets better every time you watch it.
19
American Pie (1999)
This gross-out classic launched an entire subgenre of teen comedies throughout the early 2000s. American Pie follows a group of high schoolers who make a pact to lose their virginities before they graduate. It’s a classic set-up for a raucous comedy about sex and coming of age. However, what makes American Pie stand above the rest is how it injects a clever emotional story between the lines.
The interactions between the characters make this film not just funny, but heartfelt. Oz and Heather in particular have the sweetest storyline leading up to prom. The writing makes this movie one of the more substantial comedies, while also delivering on laugh-out-loud moments such as the infamous apple pie scene.
18
Raising Arizona (1987)
After bursting onto the scene with their grisly neo-noir Blood Simple, the Coen brothers followed it up with a tonal 180-degree turn. Raising Arizona’s story sounds dark on paper – an ex-convict and his wife, desperate to start a family, kidnap one of a local businessman’s octuplets to raise as their own – but the Coens’ execution couldn’t be wackier. Most comedies use standard coverage to keep the audience’s focus on the performances and the dialogue, but Raising Arizona uses a fast-moving camera to enhance the humor.
17
Withnail And I (1987)
As with only the greatest comedy characters, almost everything Richard E. Grant’s Withnail says could be a t-shirt slogan. So beloved is the cult classic British comedy, that its most famous lines are quoted back and forth among fans in an eternal loop, celebrating the unemployed actor and his straighter sidekick (Paul McGann’s “I”). Withnail and I delightfully challenges the idea of British elegance, introducing the pair of debauched, possibly depraved down-and-outers who seek a weekend of respite in a country cottage owned by Withnail’s wealthy, lascivious uncle Monty (the excellent Richard Griffiths). Roaringly funny and desperately sad, Withnail and I gave the world Richard E Grant, thanks to his stunning breakout performance, and should be on every comedy fans’ to-watch list.
16
Popstar: Never Stop Never Stopping (2016)
Taking heavy inspiration from Rob Reiner’s This Is Spinal Tap, Popstar is a hysterical mockumentary that chronicles the career of Connor 4 Real. The film is crafted by the comedy group, The Lonely Island, and their greatest strengths are on full display. There’s plenty of outrageous moments that deliver memorable laughs, including a scene where you hear a violent altercation with a bee while the cameras are off.
What makes Popstar so special, though, is the music. The Lonely Island is known for their comedy songs, and this film features them at their absolute best. Each tune is catchy and hilarious. Plus, at a breezy 87 minutes, this is a quick and easy watch for someone wanting to check out something on the shorter side.
15
Back To The Future (1985)
When Marty McFly is flung 30 years into the past in his inventor friend’s time machine, he accidentally prevents his parents’ first meeting and has to make sure they get together so he won’t be erased from history. Back to the Future is as close to a perfect movie as there’s ever been, with a perfectly crafted script. Everything that gets set up in the present day in the opening act ends up having real significance when Marty goes back in time. What’s truly impressive is that Back to the Future manages to pack so many laughs into its airtight narrative.
14
Team America: World Police (2004)
From the twisted minds of South Park creators Trey Parker and Matt Stone, Team America: World Police did for traditional marionette puppets what The Book Of Mormon did for musicals, making the art form accessible for a new generation by dialing into the same anarchist spirit of the animation its creators are best known for.
Outrageous and provocative in equal measure, Team America skewers the perceived self-importance of actors, positioning their skills as the most valuable asset in the global fight against terrorism to frankly ridiculous results. Featuring a sex scene that needs to be seen to be believed, and a flagrant disregard for conventional offensiveness, it’s actually a far more clever parody than its ever given credit for. And it absolutely sells the idea that almost everything could be possible if the world just opened its arms to puppets more.
13
Game Night (2018)
One of the greatest surprises from the 2010s, Game Night is a hilarious comedy that has a fun premise to boot. It follows a couple named Max and Annie, whom are invited by Max’s to partake in an unusual game night featuring a kidnapping. However, when they realize what’s happening just might be real, they have to work together with their friends to save Max’s brother.
Jason Bateman and Rachel McAdams are the stars of the show for this unexpected comedy. They work incredibly well off each other and deliver some of the film’s best jokes. Plus, they’re joined by other hysterical actors and actresses that all get their time to shine. This is a comedy that’s flown under so many people’s radar, and if you haven’t checked it out yet, now is the best time to see it.
12
Blazing Saddles (1974)
Mel Brooks has made many great parody movies throughout his career, but Blazing Saddles is arguably the greatest. Blazing Saddles doesn’t just poke fun at the western genre’s clichés; it also points out the inherent racism of glorifying that period of American history. It revolves around a corrupt politician who hires a Black sheriff in an attempt to destroy a town, and the sheriff turns out to be so good at his job that he saves the town and takes down the politician and his cronies. The fourth-wall-breaking finale is a meta masterpiece.
11
Dr. Strangelove Or: How I Learned To Stop Worrying And Love The Bomb (1964)
Stanley Kubrick made his political satire Dr. Strangelove to reflect Cold War-era fears of nuclear war in the 1960s. But, since humanity is unfortunately still on the brink of nuclear annihilation, the movie is still just as timely and relevant today. Peter Sellers gives a trio of hysterical performances at the center of a star-studded cast. Dr. Strangelove has a wonderfully zany sense of humor, but its depiction of warfare and mutually assured destruction is startlingly accurate. Kubrick ends with the perfect punchline, using Vera Lynn’s “We’ll Meet Again” to show that World War II-era optimism is moot in the age of nuclear weapons.