25 Twentieth Century Comedies That Have Aged Perfectly

25 Twentieth Century Comedies That Have Aged Perfectly

There are two competing narratives when it comes to discussing the movie comedies of yesteryear. One is “Man, they don’t make ‘em like this anymore!” The other is “Man, you couldn’t make this today!” The idea is that, somewhere along the way, Hollywood lost the ability to make really great comedies — and yet, at the same time, those movies contained a lot of inappropriate jokes that wouldn’t fly in modern society. So which is it?

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Humor is subjective, as is the idea of what constitutes a great film, but what’s especially fascinating about comedies is that, in some ways, they’re not necessarily built to last. What’s funny today may not be funny, say, a decade from now — and I’m not even talking about political correctness. (Lots of topical jokes age poorly — having one-liners about Ronald Reagan in your 2023 movie probably isn’t the best idea.) For all these reasons, a comedy that stands the test of time is a remarkable feat. 

With that in mind, I decided to undertake a difficult task, selecting 25 comedies from the 20th century (in chronological order) that I think have aged, for lack of a better word, “perfectly.” What does that mean? That their humor hasn’t been dulled by time — and that it doesn’t contain a lot of cringe-y bits that are racist, sexist, homophobic or in any other way “problematic.” There are few things worse than revisiting a beloved comedy and realizing, oh god, that part doesn’t hold up at all. It’s not that a particular movie is “canceled,” but it’s sure harder to laugh at certain moments now that you know better. (For example, I adore Airplane! — it’s one of the finest comedies ever — but it definitely has a couple rough spots.)

However, I didn’t make this list to tsk-tsk certain comedic masterpieces — really, my eye was more toward highlighting funny films that have remained incredibly fresh and hilarious, no matter how old they are. (Also, I gave myself one rule: only one movie per director.) Quite astonishingly, six of the 25 films are from before 1940, and each of them would entertain a reasonable person today. I don’t consider my list to be the 25 best comedies of the 20th century, but I do think it’s a generous sampling of the different kinds of terrific comedies that still inspire filmmakers and continue to make audiences laugh. 

What’s funny is different for everybody, but I humbly suggest that if you wanted to provide an overview of the comedic peaks from the last century, these movies would be among them.

Safety Last! (1923)

Long before Tom Cruise dangled outside the Burj Khalifa in Mission: Impossible - Ghost Protocol, Harold Lloyd risked life and limb in Safety Last!, the most acclaimed of his silent comedies. Lloyd’s legacy has never matched the stature of Charlie Chaplin’s or Buster Keaton’s, but here he demonstrated his genius at physical comedy, playing a young man from the sticks who moves to the big city, hoping to make his name. Inevitably, his plan goes pear-shaped, culminating in the movie’s iconic sequence in which he climbs the side of a building. Mission accomplished, in hilarious fashion.

Sherlock Jr. (1924)

Buster Keaton wasn’t just one of cinema’s first showmen — he was an entertainer since just about birth. “My parents were already in vaudeville,” he said. “When I was four years old I became a regular.” His movies are a century old now, and not only do they hold up, they still feel innovative. Take Sherlock Jr., in which he plays a projectionist who really wants to be detective: Framed for stealing from his girlfriend’s (Kathryn McGuire) family, he tries to ascertain if his romantic rival (Ward Crane) is responsible for the crime. 

The film is best known for its second half involving the projectionist falling asleep at work, dreaming that he’s inside the film he’s showing, but at 45 minutes, Sherlock Jr. is a marvel of highly choreographed slapstick, hysterical action sequences and incredible technical skill. This silent-cinema gem is where The Purple Rose of Cairo and Last Action Hero got the big ideas for their films, but Keaton’s is still superior.  

The Gold Rush (1925)

Charlie Chaplin would make weightier films afterward, like City Lights and Modern Times, but I find myself gravitating to his third feature, which has a simple premise and a murderers’ row of great sequences. In The Gold Rush, he plays a variation on his Little Tramp persona, who’s up in Alaska prospecting for gold around some burly, intimidating-looking individuals. Things go from bad to worse when he gets snowed in with two such men (Mack Swain and Tom Murray), leading to some choice bits, including a starving Chaplin forced to eat a shoe. This is his straight-up funniest film — and for those who accuse Chaplin of being sentimental, it’s also among his least mawkish.

Trouble in Paradise (1932)

In Trouble in Paradise, Herbert Marshall and Miriam Hopkins play Gaston and Lily, master thieves who decide to team up, falling in love in the process. But when he starts to develop feelings for their new mark, played by Kay Francis, how will Lily respond? Directed by influential comedy director Ernst Lubitsch — Billy Wilder worshiped the man’s films — Trouble in Paradise is essentially the template for every “Two sexy rival spies/con artists/thieves have to work together” rom-com thriller that has hit the big screen since, but none have come close to matching this movie’s sex appeal and sparkling dialogue. Comedies are really as sophisticated as this one, and the plot is still a clockwork-like marvel of twists and turns.

Duck Soup (1933)

“If you think this country’s bad off now, just wait ‘til I get through with it.” This is but one of approximately a million zingers in this Marx Brothers gem, which was directed by Leo McCarey and featuring Groucho as Rufus T. Firefly, who’s talked into becoming the new leader of Freedonia, an impoverished nation that will eventually go to war with its neighbor Sylvania. Duck Soup is silly and sexy and then silly again, the laughs tumbling one after another as Groucho and his mates, alongside top-notch performances from Margaret Dumont and Raquel Torres, go for jokes wherever they can find them. Bad puns, goofy wordplay, balletic physical comedy, irreverent musical numbers: Here’s everything that made the Marx brothers great in just 68 minutes.

It Happened One Night (1934)

There have been plenty of racier movies over the ensuing decades, but Frank Capra’s Oscar-winning screwball comedy is still incredibly sexy. There’s no nudity or sex in It Happened One Night, but it’s the interactions between hard-drinking journalist Clark Gable and socialite-on-the-run Claudette Colbert that makes this film such a turn-on, the innuendo, romantic tension and the occasional flash of spectacular thigh so incredibly titillating. The characters don’t initially hit it off, but you sense their attraction from the start, and Robert Riskin’s screenplay (based on a Samuel Hopkins Adams short story) makes their sharp, funny banter feel like foreplay. 

His Girl Friday (1940)

You won’t find a bigger fan of His Girl Friday than Gillian Jacobs. “Cary Grant was my first big crush in life,” she told Cracked this year. “I wish I could be in one of those movies. I aspire to Rosalind Russell level of fast repartee and that back and forth — that (verbal) tennis match between her and Cary Grant, I would kill for that.” 

Howard Hawks’ masterful screwball comedy paired the two stars as a hard-driving newspaper editor (Grant) who doesn’t want his ex-wife (Russell), a former journalist, to remarry, tempting her with one last juicy story. What follows are twists, turns, suspense and the fastest rat-a-tat-tat dialogue the movies may have ever seen, with the onetime lovers jarring and flirting all at once. His Girl Friday ought to be exhausting — and lord knows modern movies that try to mimic its style usually are — but the effect is pure exhilaration. 

The Philadelphia Story (1940)

I have no sympathy for the “They don’t make movie stars like they used to!” argument, but it’s hard to think of a film blessed with more genuine silver-screen talents than The Philadelphia Story, which is a romantic comedy involving Cary Grant and James Stewart dueling for the affections of Katharine Hepburn. (Amazingly, this was the second of two classic rom-coms both Grant and Stewart would make in 1940 — alongside, respectively, His Girl Friday and The Shop Around the Corner.) The plot: Hepburn is about to remarry, but her ex-husband Grant attends the wedding (along with reporter Stewart, who’s there to write a story), the two dashing men making her wonder if she’s made a mistake. This swoon-worthy film hasn’t lost a bit of its wit, with all three leads delivering some ace one-liners as they duke it out to secure their own happy ending. 

Sullivan’s Travels (1941)

Comedy is often viewed as not as worthy as drama — the idea being that true art comes from depicting serious subject matter. Preston Sturges, one of Hollywood’s greatest comedic filmmakers, took issue with that notion, never more succinctly than in Sullivan’s Travels, which is about the very notion that laughter is just as important as any other reaction to art. The movie stars Joel McCrea as a successful comedy director who wants to make something more “meaningful,” deciding to disguise himself as a pauper so that he can understand what life is like for “real” Americans. 

Co-starring Veronica Lake, Sullivan’s Travels has its moments of searing drama, but it’s largely a satire of the sort of self-important thinking that still infects Hollywood during Oscar season. Fun fact: The Coen Brothers’ got the title for their period comedy O Brother, Where Art Thou? from the super-somber drama McCrea’s character is aiming to film to prove he’s an artist.

Miracle on 34th Street (1947)

Released during the summer of 1947, which back then was a far bigger time for movie attendance than Christmastime, Miracle on 34th Street has since been rightly recognized as one of the greatest of all holiday films. Part love story, part anti-capitalist takedown, the Oscar-winning heartwarmer is also really funny, chronicling a quirky fellow man named Kris Kringle (Edmund Gwenn) who arrives in Manhattan, telling anyone who will listen that — no, really — he’s Santa Claus. Lessons about the true meaning of Christmas are intermingled with the charming romance between sweet single mom Maureen O’Hara and chivalrous lawyer John Payne. But this classic’s success hinges on Gwenn, who nabbed the Academy Award for Best Supporting Actor as Kris, a jolly soul who finds New York both endlessly delightful and seriously screwed-up. For generations to come, he was viewers’ idealized picture of Santa Claus — a witty grandfatherly figure who had no problem being slightly naughty if someone was acting like a jerk. 

Sunset Blvd. (1950)

The initial reactions to Billy Wilder’s dark skewering of Tinseltown weren’t unanimously glowing. As the Oscar-winning filmmaker later recalled, “(MGM head) Louis B. Mayer (was) shaking his fist saying, ‘We should horsewhip this Wilder, we should throw him out of this town, he has brought disgrace on the town that is feeding him!’ I don’t know what he was talking about, I don’t know what the hell was so anti-Hollywood in that picture.” Anyone who’s seen Sunset Blvd. could explain it to Wilder: In this story of a cynical, struggling screenwriter (William Holden) who gets mixed up with a vain, has-been movie star (Gloria Swanson), he created the definitive portrait of a soulless showbiz community that will sleep with (or murder) anyone in order to get ahead. The blackhearted characters are monstrously funny, and every zinger draws blood.   

Singin’ in the Rain (1952)

A loving send-up of the end of the silent era, Singin’ in the Rain features as many memorable set pieces as any Hollywood musical. It’s also the funniest, with Gene Kelly and Donald O’Connor endlessly delightful as best buds navigating the weirdness of these newfangled talking pictures. Debbie Reynolds was far more than the stereotypical romantic interest, proving to be a perfect comedic foil to Kelly’s self-important matinee idol. (She could sing and dance pretty damn well, too.) And then there’s Jean Hagen, whose temperamental, ego-driven, delusional actress Lina Lamont was an enjoyable villain — the kind of star who, because of her screechy voice, was about to be pushed aside by sound cinema. No matter how many times you’ve seen Singin’ in the Rain, you’ve never seen it enough. It’s wonderful, every single time.  

Dr. Strangelove (1964)

Only Stanley Kubrick would find the idea of the world ending in nuclear annihilation funny. Adapting the tense doomsday novel Red Alert for the big screen, the filmmaker started seeing the potential for humor. “My idea of doing it as a nightmare comedy came in the early weeks of working on the screenplay,” he explained, later adding, “I found that in trying to put meat on the bones and to imagine the scenes fully, one had to keep leaving out of it things which were either absurd or paradoxical, in order to keep it from being funny; and these things seemed to be close to the heart of the scenes in question.” 

The result was Dr. Strangelove, which is as chilling as it is comedic, depicting the warmongering generals, evil scientists and ineffectual politicians who will probably bring about our destruction. Nuclear war isn’t as big a fear now as it was during the Cold War when the film came out, but the underlying anxiety remains — you laugh at Dr. Strangelove because you don’t want to freak out. 

The Producers (1967)

No filmmaker is more at the center of the “Could this movie be made today?” debate than Mel Brooks. The man who once described comedy as “the lecherous little elf whispering in the king’s ear, always telling the truth about human behavior” has unapologetically pushed the boundaries of tastefulness in his films to make points about racism and fascism, provoking shock and laughs in equal measure. Of all his movies, though, the one I like best is his first, which won him an Oscar for screenwriting. The Producers paired Zero Mostel’s shameless huckster and Gene Wilder’s anxious accountant, who together decide to produce a sure-to-be-a-flop musical… except it turns out to be the hit Springtime for Hitler. The stupidity of the general public and the sleaziness of the entertainment industry are just two of this film’s many targets. Adolf Hitler has never been funnier. 

Playtime (1967)

Like the silent auteurs who came before him, writer-director-star Jacques Tati didn’t need dialogue to make audiences laugh. Over a series of films, he played Monsieur Hulot, an ordinary Frenchman who finds himself in one overwhelming situation after another, leading to droll physical comedy. Tati’s peak was Playtime, which sends Hulot into a futuristic Paris where technology is starting to dehumanize society. And yet, this film doesn’t feel dour because Hulot’s bizarre interactions with big-city life are always funny and visually arresting. (Tati built an entire world for Playtime, his camera often making Hulot small in the frame, the character literally dwarfed by modern life.) The meticulously mapped out comedy set pieces are incredible, and the brilliant production design has been an inspiration for everything from The Terminal to The French Dispatch to Barbie.   

The Heartbreak Kid (1972)

Working from Neil Simon’s script, itself based on a Bruce Jay Friedman short story, director Elaine May crafted a comedic nightmare scenario: On his honeymoon, Lenny (Charles Grodin) falls in love with Kelly (Cybill Shepherd), suddenly realizing he made a mistake marrying unexciting Lila (Jeannie Berlin). The Heartbreak Kid is an impeccable dark comedy that walks a delicate line, illustrating what a jerk the scheming Lenny is while, somehow, making us actually feel somewhat for the guy. Outside of Midnight Run, this may be Grodin’s finest performance, playing a restless young man who abandons one woman in the desperate pursuit of another. Decades later, the Farrelly Brothers tried remaking the movie with Ben Stiller — they failed miserably. 

Annie Hall (1977)

Long before he was accused of childhood sexual abuse, Woody Allen was the preeminent American comedy filmmaker of the 1970s and 1980s. Annie Hall won Best Picture, following insecure stand-up Alvy (Allen) as he sifts through the pieces of his failed relationship with rising singer Annie (Diane Keaton, who took home Best Actress). Rethinking the romantic comedy as a neurotic character study and an existential exploration of what makes life worth living, Allen made falling in (and out of) love endlessly bittersweet without skimping on the one-liners and sight gags. 

The King of Comedy (1982)

Inevitably, Martin Scorsese’s disturbing examination of celebrity and fandom inspires the question, “So, wait, is this actually a comedy?” My response: Yes, but a very, very dark one. Released in the wake of John Lennon’s murder, The King of Comedy spoke to a new era in which the famous lived in fear that some unstable supporter would come after them, with Robert De Niro’s Rupert Pupkin a talentless stand-up obsessed with befriending Jerry Langford (Jerry Lewis), America’s biggest talk-show host. Although there are great jokes in the film, you don’t so much laugh at The King of Comedy as recoil at its implications, wondering just how sick certain elements of our society have become in their quest to get in the spotlight. Reality TV would soon be on its way — not to mention the rise of unhealthy parasocial relationships with celebrities thanks to social media. The movie is funny, but it’s also scary.

This Is Spinal Tap (1984)

“What’s wrong with being sexy?” The mockumentary that skewered the pretentiousness of rock bands remains both astoundingly funny and a trenchant takedown of the sexism and stupidity that still dominate aspects of the music industry. This Is Spinal Tap grimly chronicled bandmates Derek Smalls (Harry Shearer), David St. Hubbins (Michael McKean) and Nigel Tufnel (Christopher Guest) as their once-sorta-popular heavy metal group fades into obscurity, an immutable fact that even these dummies finally catch wind of. Their belief in their artistry, matched by their utter incompetence, remains both hilarious and oddly moving.

Stranger Than Paradise (1984)

“There’s something very American about the film and yet formally, it’s not traditional at all, it’s very untraditional,” Jim Jarmusch said about his breakthrough comedy. “That comes from the way I write, which is backwards: Rather than finding a story that I want to tell and then adding the details, I collect the details and then try to construct a puzzle or story.” Stranger Than Paradise is a wonderfully droll look at three eccentric individuals — a couple of buddies (John Lurie and Richard Edson) and one of the men’s cousin (Eszter Balint) — as they hang out, ponder life and, eventually, make their way from New York to Cleveland. Jarmusch’s low-key, deadpan style allows the humor to emerge from the blankness of these very ordinary people who seem thrown by life itself. Not just funny but very hip, Stranger Than Paradise helped launch the American independent cinema movement of the 1980s, which found the comedy in the offbeat. 

Raising Arizona (1987)

Early in their career, Joel and Ethan Coen often set their movies in specific genres that they’d subvert or upend. But when they approached the writing of the screwball comedy Raising Arizona, Ethan said, “(W)e did not start off thinking about working with a genre. We intended, in a general way, to make a comedy with two principal characters. Our concentration was on them, rather than on what the film would be in terms of type.” And so began the wacky saga of ex-con Hi (Nicolas Cage) and ex-cop Ed (Holly Hunter), who get married but discover they can’t conceive, deciding instead to steal somebody else’s. The Coen Brothers’ comedies can be hit (Burn After Reading) or miss (Intolerable Cruelty), but Raising Arizona is all madcap hilarity, with Cage’s none-too-bright protagonist the calm, off-kilter center of this increasingly surreal extravaganza.  

Broadcast News (1987)

A few years earlier, James L. Brooks’ Terms of Endearment won multiple Oscars, including Best Picture. But his follow-up is the superior picture. The grown-up romantic comedy Broadcast News is a virtuoso portrait of personal ethics and the struggle to strike a balance between one’s personal and professional life, following news producer Jane (Holly Hunter) as she struggles with her network’s desire to move away from hard-hitting journalism. She’s joined in her fight by loyal coworker Aaron (Albert Brooks), who’s quietly in love with her, but despite herself, she falls for shallow new anchor Tom (William Hurt). A workplace comedy that’s often hysterical — poor Aaron and his disastrous on-camera anchor spot — Broadcast News has only grown in stature over the years as the media keeps finding new and even more depressing ways to dumb down.

Babe (1995)

Comedies don’t get nominated for Best Picture very often — neither do kids’ films. And yet, Babe pulled off that feat, telling the story of an adorable pig (voiced by Christine Cavanaugh) who proves to be an expert sheepherder. This touching fable was groundbreaking at the time for how it managed to make it seem like its animal characters could talk, but the film has endured as a bighearted comedy about fitting in. (Plus, James Cromwell is endlessly endearing as the crusty farmer who comes to love Babe.) Turns out, Babe isn’t just a good movie for children — its playful spirit and winning sense of humor make it a pretty universal film. 

Toy Story (1995)

There have been plenty of iconic mismatched comedy duos. Laurel and Hardy. Oscar and Felix. But don’t forget about Woody (Tom Hanks) and Buzz (Tim Allen): Pixar’s first feature-length film introduced us to the toy cowboy and space-ranger action figure, who initially can’t stand one another. (Woody is jealous of this fancy new toy, while Buzz is irritated that this cowboy keeps insisting he’s not a real interplanetary explorer.) Toy Story did more than launch the Pixar narrative model — it showed how animation could craft hysterical stories whose comedy was sharp without being cruel, wholesome without being lame. Just about everybody in Toy Story has at least one great line — Don Rickles as Mr. Potato Head has several — and the film’s heartwarming message about friendship and accepting change is still plenty potent.  

Election (1999)

What if all of life was just like high school? Alexander Payne’s second feature, an adaptation of the Tom Perrotta novel, was a devastating satire about a likable but discontented teacher (Matthew Broderick) who resents overachieving teenager Tracy Flick (Reese Witherspoon), determined to do whatever he can to make sure she doesn’t win the school’s presidential election. Skewering politics, popularity and the insidiousness of middle-aged men who feel like life has shafted them, Election is a brilliantly bitter comedy about winners and losers, setting the stage for Payne’s Oscar-winning career and Witherspoon’s superstardom. 

The century’s great comedies often feel timeless — this portrait of ruthless ambition still seems prescient decades later.

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