Some Like It Hot & 9 Other Timeless Comedy Masterpieces

Due to the ever-changing nature of humanity’s collective sense of humor, comedies are the quickest movies to age and the most likely to age poorly. Very few comedies have been able to stand the test of time. Whereas the work of Charlie Chaplin, Buster Keaton, and the Marx brothers can be enjoyed a century later, some raunchy, flagrantly offensive comedies from the early 2000s are unwatchable today (and, in some cases, were unwatchable back then, too).

Billy Wilder’s Some Like It Hot, now more than 60 years old, is a prime example of a comedy that has stood the test of time.

10 Some Like It Hot (1959)

Set in Prohibition-era Chicago, Some Like It Hot stars Tony Curtis and Jack Lemmon as a couple of musicians on the run from the mob who disguise themselves as women to join an all-female band touring the country. Marilyn Monroe steals the show as Sugar Kane, the band’s vocalist and ukulele player, who both guys fall for immediately.

The final scene of Some Like It Hot is one of the most iconic endings in the history of comedy movies, concluding the story on the perfect punchline.

9 His Girl Friday (1940)

Directed by Howard Hawks, His Girl Friday is a screwball comedy classic starring the perfectly matched Cary Grant and Rosalind Russell. Adapted from The Front Page, His Girl Friday is an early example of a gender-swapped remake.

Noted for its snappy dialogue, the movie revolves around a newspaper editor’s attempts to win back his reporter ex-wife when she announces her re-marriage to another man.

8 Singin’ In The Rain (1952)

A lighthearted portrayal of Hollywood circa the 1920s, Singin’ in the Rain charts the difficult transition from silent films to “talkies.” Gene Kelly plays a Hollywood star who can hardly stand his studio-appointed co-star, a vain diva played by Jean Hagen.

When her shrill voice holds her back in the talkie era, Kelly sees an opportunity to replace her with a much warmer, more talented performer played by Debbie Reynolds.

7 The Producers (1967)

While its subject matter was a point of controversy on its initial release, the satire of Mel Brooks’ The Producers is timeless. A struggling Broadway producer and an accountant team up to stage the worst play ever put on, hoping that a historically short run will send their investors running for the hills, allowing them to make more money from a flop than a hit.

However, it doesn’t exactly go according to play. They put on a show that’s guaranteed to bomb — Springtime for Hitler, an extravagant musical glorifying the Third Reich — and, much to their surprise, audiences fall in love with it.

6 The Ladykillers (1955)

One of the funniest (and darkest) British comedies ever made, The Ladykillers stars Alec Guinness as a criminal mastermind who rents a few rooms from an old lady for the crew of his latest heist. Little does he know, her favorite hobby is reporting suspicious activity to the police.

Although the heist goes off without a hitch, the woman catches them red-handed during the escape. They agree they have to kill her, but they’re all so inept that they end up killing each other first.

5 When Harry Met Sally (1989)

Chronicling the long, complicated relationship of two platonic friends who need to realize they love each other, When Harry Met Sally just might be the greatest romantic comedy ever made.

Rob Reiner’s sharp direction and Nora Ephron’s perceptive script hilariously capture the ups and downs of modern dating, while Billy Crystal and Meg Ryan’s on-screen chemistry is unparalleled.

4 Jour De Fête (1949)

Jacques Tati is one of the greatest comedy filmmakers who ever lived. All of his films are timeless classics whose gags both hold up today and cross the language barrier.

Tati’s masterfully simplistic feature directorial debut, Jour de fête (The Big Day), stars the director himself as a mailman going about his day and facing constant setbacks in a small French village. The bare-bones production utilized unknown actors for major roles and villagers from the shooting location, Sainte-Sévère-sur-Indre, for smaller parts.

3 Dr. Strangelove (1964)

Stanley Kubrick produced Dr. Strangelove at the height of the Cold War. It involves the threat of a nuclear holocaust as U.S.-Soviet tensions come to a head. Initially, the story was supposed to be told as a straight political drama, but Kubrick found the events of the plot to be so absurd that it would work better as a comedy.

With a trio of hysterical performances by Peter Sellers and an abundance of jokes that still land today, Dr. Strangelove is arguably the greatest political satire movie ever made.

2 Monty Python And The Holy Grail (1975)

When the Monty Python troupe brought their uniquely absurdist comic sensibility to the big screen, it didn’t disappoint. Monty Python and the Holy Grail is a lampoon of the Arthurian legend, a masterpiece of meta, and a deconstruction of the filmic form itself.

The movie’s everything-and-the-kitchen sink approach is held together by Graham Chapman’s exasperated turn as King Arthur and the cohesive, airtight structure of the script.

1 Airplane! (1980)

One night, David Zucker, Jim Abrahams, and Jerry Zucker happened to catch the old black-and-white disaster movie Zero Hour! on TV. The trio copied the ridiculous story and trite characters of this movie so closely in crafting their hysterical debut feature Airplane! that Paramount ended up having to buy the remake rights.

The great thing about Airplane! is that it works as more than a spoof. It plays as a straight comedy for viewers who aren’t familiar with Zero Hour! (which is almost everyone). It’s wall-to-wall jokes and all the jokes land.

About The Author

Ben Sherlock
(3485 Articles Published)

Ben Sherlock is a writer, comedian, independent filmmaker, and Burt Reynolds enthusiast. He writes lists for Screen Rant and features and reviews for Game Rant. He’s currently in pre-production on his first feature (and has been for a while, because filmmaking is expensive). You can catch him performing standup at odd pubs around the UK that will give him stage time. Previously, he wrote for Taste of Cinema, Comic Book Resources, and BabbleTop.

More From Ben Sherlock