1950s Comedies That Work Pretty Well in 2023

5 Harvey

We all love Jimmy Stewart, the legendary star of classics like Rear Window and Mr. Smith Goes to Washington — not to mention the timeless holiday staple It’s a Wonderful Life, in which he played George Bailey, the buzzkill who saves Bedford Falls from the evils of jazz. But Stewart’s favorite film role was Elwood P. Dowd, the lovable eccentric who claims that his best friend is an invisible, six-foot-tall rabbit (or “puca”) named “Harvey.”

Much of Harvey is still delightful today; some have even argued that the story of Harvey, which very nearly finds the pleasant Elwood being committed to a sanatorium (and, quite likely, lobotomized) before ultimately being accepted by his family, is “an unexpectedly progressive view of mental health” for the time. Then again, some have claimed that the movie falsely suggests that mental illness is “a delightful state of mind.”

But Harvey — despite some clunky moments and sexist attitudes — mostly works today, less as a specific story about mental health and more as a broader allegory for how society strives to oppress those who dare to veer from a “traditional” worldview. Hopefully, this movie won’t one day be ruined by Harvey: Origins, starring a CGI bunny voiced by Chris Pratt.

4 The Court Jester

Bing Crosby’s White Christmas co-star Danny Kaye famously starred in The Court Jester, a technicolor spoof of Robin Hood-esque swashbuckling adventures. The 1955 musical comedy finds Kaye playing a medieval rebel named Hubert Hawkins, who disguises himself as a royal comedian while protecting the rightful (infant) heir to the throne.

It’s a fun romp that is, in many ways, very dated (few movies today are filmed in glorious VistaVision), but at the same time, The Court Jester anticipated future period comedies like Monty Python and the Holy Grail and The Princess Bride. But no movies have bested the wordplay genius of the “vessel with the pestle” scene.

Come for the jokes; stay for young Angela Lansbury…

3 The Long, Long Trailer

Lucille Ball is understandably famous for her iconic television career, which included starring in I Love Lucy and producing some show about outer space. But Ball was a major movie star as well, as evidenced by films like Vincent Minelli’s The Long, Long Trailer, which also starred her husband and creative partner Desi Arnaz. 

The Long, Long Trailer is basically just I Love Lucy: The Movie, with Ball and Arnaz playing a newlywed couple not so dissimilar from the Ricardos, but instead of spending most of their time in a colorless apartment, they travel the country in a ginormous, state-of-the-art mobile home.

The movie is both very funny and, occasionally, more nerve-racking than most thrillers.

2 The Trouble With Harry

Legendary director Alfred Hitchcock isn’t really known for his comedy, despite the occasional moment of black humor in his films, some TV appearances, and the time he slipped a crew member some laxative-infused brandy, causing him to shit all over himself. But Hitch once made a legit comedy movie, the hilariously grim The Trouble with Harry.

Ever wonder what would happen if the kid from Leave It to Beaver randomly stumbled upon a dead body? That’s basically the premise of The Trouble with Harry, which finds the residents of a small town struggling to figure out what to do with Harry’s remains after he’s discovered in the woods. While the movie was a major flop back in 1955, its grimly absurd tone was arguably way ahead of its time, laying the foundations for future corpse-based comedies like Weekend at Bernie’s and Daniel Radcliffe’s Swiss Army Man.

1 Some Like It Hot

The rare movie to turn real-life gangland murders into comedy gold, Billy Wilder’s 1959 Marilyn Monroe vehicle Some Like It Hot, about two jazz musicians hiding from mobsters amongst an all-female band, has become a classic.

You might think that a 64-year-old comedy about two cisgender men donning women’s clothes would, today, be relegated to the ash heaps of movie history, but that’s not really the case. For one thing, Some Like It Hot was extremely progressive for its time; its non-traditional gender roles irked Hollywood’s self-censorship system, The Hays Code, leading Wilder to controversially release the film without their certificate of approval. The movie was banned in Kansas and condemned by the Catholic League of Decency for being “seriously offensive to Christian and traditional standards of morality and decency.” 

Much of the movie is still dated, and the very premise of men using dresses as a means of disguise “plays into the man-in-a-dress transphobic trope.” But looking back at the film now, it is nevertheless admirable that the movie affords so much space to the idea of exploring gender fluidity, at a time when most male movie stars were grizzled slabs of meat with slicked-back hair. Jack Lemmon’s character Jerry genuinely comes to enjoy his life as “Daphne” and even gets engaged to another man.

When Daphne’s fiancé learns about Jerry, he just casually accepts them, uttering one of the most famous final lines in movie history.

Of course, all of this was still ultimately played for laughs back in 1959, but it didn’t take too much narrative tweaking for the recent Broadway musical adaptation to turn Daphne’s story into a more explicit arc of self-discovery.

As Out Magazine pointed out, most of the movie’s humor doesn’t come from mocking the idea of dudes wearing dresses but rather “their earnest attempts to be women.” Although the movie’s pros probably don’t outweigh the big con: that it eventually led to White Chicks.

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