The 12 undisputed best comedy movies of all time

“When I invite a woman to dinner I expect her to look at my face. That’s the price she has to pay.” Let’s kick things off with a classic, featuring three undisputed icons of comedy. The Marx Brothers, a real-life family that rose to fame as a vaudeville troupe, took Hollywood by storm with a series of raucous comedy movies. A Night at the Opera is a contender for their very best, thick with rapid-fire wordplay, ingenious insults, and racy innuendo that they only got away with because the film production business hadn’t been regulated yet. In this film, Groucho Marx plays Otis B. Driftwood, the squirrelly business manager for a wealthy opera investor, while brothers Chico and Harpo Marx play the bumbling sidekicks of a humble background singer who is on the other side of a love triangle with a famous tenor. All of them end up on a steamer ship sailing from Italy to New York, where hijinks ensue. The plot isn’t so much the point in this movie as the frenetic pacing that moves the brothers from one gut-busting situation to another. As amazing as the Marx Brothers are in this film, their zany antics wouldn’t be half so hilarious without straight man … excuse me, woman … Margaret Dumont, who finds a hundred different ways to look aghast as the brothers run circles around her hand-wringing image of propriety.

One of the great comedies from Hollywood’s golden era, Some Like It Hot is anchored by three wonderful performances from Tony Curtis, Jack Lemmon, and above all, Marilyn Monroe. Telling the story of two musicians who accidentally witness the St. Valentine’s Day massacre and are forced to dress in drag to join an all-female band, the movie holds up to modern standards far better than you might expect. Marilyn Monroe’s image as a star is often flattened, but in Some Like It Hot, we get to see all that she was capable of. She’s sensitive, vulnerable, strong, and has perfect comic timing. It’s a remarkable performance in one of the all-time great comedies. 

“Gentlemen, you can’t fight in here! This is the war room.” Dr. Strangelove is pretty easily one of the greatest black comedies ever made. Kubrick is not typically thought of as a comedic director, but his style matches perfectly with this movie’s secret weapon: Peter Sellers, Peter Sellers, Peter Sellers. An actual genius who plays three parts in one of the greatest performances in film history. On top of all of that, Strangelove is one of the smartest movies ever made about the nuclear age, comedy or not.

“This is a very complicated case, Maude. You know, a lot of ins, a lot of outs, a lot of what-have-yous.” Loosely based on the detective novels of Raymond Chandler, this Coen brothers comedy follows consummate slacker Jeffrey “The Dude” Lebowski, who is rudely interrupted mid-toke by a pair of thugs who have mistaken him for a wealthy philanthropist with the same last name. When they realize their error, one of them takes a contemptuous piss on The Dude’s rug, sending The Dude on a mission to get a replacement from the rich guy they mistook him for. But the Big Lebowski has a different mission for The Dude — to find his missing trophy wife, Bunny. Against orders, The Dude enlists the help of his bowling buddies, rageaholic Walter and dimwitted Donny. From there, the plot twists and coils in on itself like a riled-up rattlesnake. Aside from the bizarre characters and the labyrinth of red herrings, one of the best things about this comedy is how it demands multiple viewings to fully appreciate it. You’ll know you’ve watched it enough times when you can have an entire conversation just using quotes from the film.