All 94 Best Picture Winners, Ranked by How Funny They Are
On Sunday, we’ll learn which of 10 movies will walk away with the most coveted prize in all of Hollywood: Best Picture. Plenty of listicles will be published this week ranking the movies that are part of that elite club. But those rankings usually focus on how good or bad the films are. Rarely do they use only one criterion to make their determination: How funny are they?
Humor is subjective — what you think is amusing might not make me laugh, and vice versa. Nonetheless, I decided to take on the daunting task of trying to figure out which Best Picture winners are the most hilarious. And I don’t mean unintentionally funny. I’m talking about actual, legitimate chuckles and guffaws.
While putting together these rankings, what became clear pretty quickly is that many winners actively didn’t try for humor at all — mostly because their subject matter is utterly unconducive to comedy. (You could argue that’s what helped them win — after all, Academy voters are notorious for valuing seriousness over silliness.) And yet, there are a few out-and-out comedies that have taken home the big prize. Somewhere in between those two poles is a wide swath of motion pictures, usually dramas, that can also have some really funny elements to them. The same is true of this year’s nominees: Depending on your perspective, The Banshees of Inisherin is either a bleak tragedy or one incredibly dark comedy.
So with that in mind, let’s jump into the rankings. Are you ready to laugh? Well, too bad: You’ll have to wait for a bit while you scroll down until you find a legitimately funny film.
Schindler’s List (1993)
One of two Best Picture winners Seinfeld lampooned because of its serious tone, the toweringly somber Schindler’s List is barely, briefly funny because of Ralph Fiennes’ utterly pathetic Nazi commander. But that’s it.
12 Years a Slave (2013)
If there is one Best Picture winner this century that is the least seen — not because it’s bad, but because it’s so, so hard to watch — it’s Steve McQueen’s harrowing depiction of slavery. Maybe there’s a random bit of gallows humor to be found amidst 12 Years a Slave’s anger and pain, but who could possibly laugh in the face of such horror?
The goings-on of a well-to-do British family are chronicled over several decades in this clunky drama from Hollywood’s early days. Cavalcade won Best Picture and was rarely discussed afterward.
All Quiet on the Western Front (1930)
Director Lewis Milestone crafted one of the definitive anti-war films, adapting Erich Maria Remarque’s novel. That same material was the source material for this year’s Netflix Best Picture nominee. A startling experience, All Quiet is all serious.
The Broadway Melody (1929)
In the late 1920s, Hollywood was gingerly pivoting to talking pictures. As The Broadway Melody demonstrates, they hadn’t yet figured out how to translate humor to this new format.
Oliver Stone turned his Vietnam experiences into this sobering war drama. Platoon wanted you to know there was definitely nothing funny about a conflict that had needlessly destroyed so many lives.
The Last Emperor (1987)
Humor wasn’t on director Bernardo Bertolucci’s mind when he crafted this sweeping, decade-spanning epic about Pu Yi, China’s last emperor. You won’t laugh when you watch The Last Emperor, but you will be transported.
Westerns can be funny — and, no, I don’t mean Blazing Saddles. But this derided, dated dud sure isn’t.
The Life of Emile Zola (1937)
A portrait of the French author (Paul Muni), who was instrumental in freeing an officer wrongly accused of treason, this biopic is powerful. Not surprisingly, though, it’s not exactly mirthful.
Kramer vs. Kramer (1979)
Turns out, a movie about the rise in divorce in America had very few hilarious moments.
The epitome of the tasteful, slightly staid biopics that sometimes win Best Picture, Gandhi pays tribute to the greatness of Mahatma Gandhi. An irreverent comedy, it is not.
Mrs. Miniver (1942)
A film unequivocally designed to rally viewers to the worthy cause of defeating Germany, Mrs. Miniver stars Greer Garson and Walter Pidgeon as a British married couple who find themselves both getting involved in World War II. (He goes in his boat to help rescue soldiers trapped at Dunkirk; she squares off with a Nazi pilot who’s shown up at her home.) There wasn’t much place for humor in a movie meant to be well-made propaganda.
The very first Best Picture winner, which back then was called Outstanding Picture. (That same Oscars, Sunrise won the prize for “Unique and Artistic Production.”) Featuring innovative aerial combat sequences, especially for its time, Wings is a romantic drama set against the backdrop of World War I. Charles Chaplin, Buster Keaton and Harold Lloyd demonstrated silent film’s comedic potential, while Wings’ epic scope suggested how the art form could create big-screen spectacle.
William Shakespeare’s grand tragedy has comedic elements, but director-producer-star Laurence Olivier removed them for his adaptation, giving us a treatment of the melancholy prince that’s widely regarded as the best movie Hamlet. Just don’t expect any comic relief: Funnier characters like Rosencrantz and Guildenstern aren’t here.
How Green Was My Valley (1941)
Everybody has that one friend who loves pointing out that this is the movie that beat Citizen Kane for Best Picture. Well, tell that friend that this John Ford drama, about a working-class Welsh family, has plenty of fans — and that, for our purposes, isn’t all that funny because of what these people have to endure.
The Best Years of Our Lives (1946)
When people think of war movies, their mind tends to go to films set in the midst of battle. But this William Wyler character drama is the other kind, chronicling a few soldiers who have returned home from World War II, as well as the people who welcome them back after being gone so long. The Best Years of Our Lives is an intimate stunner: It runs nearly three hours long and calmly documents the challenges troops face after the fighting stops. This was long before conditions like PTSD were widely discussed, making The Best Years of Our Lives even more of a groundbreaker. I love Best Years, but don’t go looking for lots of laughs.
Ordinary People (1980)
For his directorial debut, Robert Redford made an austere drama about a family riven by the death of its eldest son. Comedy was in short supply in Ordinary People’s study of guilt and forgiveness, although I think it speaks to how much Redford would grow as a filmmaker that, more than a decade later, he delivered the even-better Quiz Show, which was also bitingly funny.
Mel Gibson, what a card.
Charlton Heston, what a card.
A beautifully told story of a young man over the course of three crucial periods in his life, Moonlight is heartbreaking but not especially hilarious. No one who adores this movie has ever complained.
Gentleman’s Agreement (1947)
It’s depressing that the themes of this Elia Kazan drama remain relevant: Gregory Peck plays a Gentile journalist writing a story about anti-Semitism in New York, in the process having his eyes opened about the alarming amount of bigotry and hatred around him. Gentleman’s Agreement is very much a Message Movie, but the message is still pretty pertinent. Clearly, there’s nothing funny about this film.
The Greatest Show on Earth (1952)
This forgotten Cecil B. DeMille production has recently enjoyed a bit of a second life thanks to The Fabelmans. (This is the movie young Sammy sees in the theater, sparking his lifelong love of cinema.) But that hasn’t improved its reputation as one of the worst of all Best Picture winners. It’s pretty low on this list, too, but that’s only because DeMille’s salute to the circus doesn’t have many laughs in it.
All the King’s Men (1949)
Some films about politics are bruising satires. All the King’s Men is not one of those: Inspired by crooked Louisiana governor Huey Long, this angry drama stars Broderick Crawford as Willie Stark, a seemingly conscientious politician who wants to change the system — it’s only after he’s elected that he reveals his true malicious streak. Writer-director Robert Rossen, adapting Robert Penn Warren’s novel, doesn’t have time for jokes. He’s too busy seething.
Mutiny on the Bounty (1935)
A battle of wills between Charles Laughton’s villainous Captain Bligh and Clark Gable’s noble Fletcher Christian, Mutiny on the Bounty wowed Oscar voters because of its seering treatment of the 1932 novel. Chuckles are few and far between.
The Deer Hunter (1978)
The first great (but also controversial) film about the Vietnam War, The Deer Hunter doesn’t offer many lighthearted moments. Even when Robert De Niro and his buddies are enjoying time together before they’re shipped overseas, you can feel the tension in their sinking sense that something terrible could happen — which it eventually does.
A Man for All Seasons (1966)
A film about staying true to your beliefs — no matter what — A Man for All Seasons stars Paul Scofield as Sir Thomas More, who refuses to go along with King Henry VIII’s (Robert Shaw) request to have his marriage to Catherine of Aragon annulled. More than a little dry, the film is literate and important, and not very funny.
A Beautiful Mind (2001)
It’s hard to find many jokes in this sappy, blandly inspirational drama about tortured mathematician John Nash. A Beautiful Mind won Best Picture over Gosford Park, a better (and funnier) film.
Funny just isn’t Russell Crowe’s thing, as demonstrated by his back-to-back Oscar-winning dramas. At his peak, he portrayed a rugged nobility that wasn’t meant to be especially humorous. That said, Joaquin Phoenix is fun as the spoiled, illegitimate rule.
Not held in as high regard as other musicals of the period, Gigi can’t help but feel cringey by modern standards. (This movie is about a young woman, Leslie Caron, who’s being groomed to be a courtesan for rich men.) But if you can get past what’s problematic, this remains a fairly charming film.
The only Alfred Hitchcock movie to win Best Picture doesn’t feel like the director’s in several regards. And one of them is that Rebecca lacks the dark humor that films like North by Northwest and even Vertigo and Psycho have. Not that Hitchcock didn’t try to bring some levity to the proceedings, although his comedic ideas were nixed by powerful producer David O. Selznick. If you’re looking for Funny Hitch, though, several of his classics are filled with deft little moments of black comedy.
In the Heat of the Night (1967)
An issue-driven film, as well as a tense mystery, In the Heat of the Night paired Sidney Poitier’s sharp Philadelphia detective and Rod Steiger’s mistrustful Mississippi police chief. America’s racial divide was the movie’s subtext, with comedy understandably not part of the equation.
Out of Africa (1985)
A few years earlier, Sydney Pollack made a classic comedy, Tootsie. Out of Africa was not that. This was an epic romance starring Robert Redford and Meryl Streep, which is the sort of thing Academy voters gravitate to.
You probably wouldn’t expect a lot of chuckles from an adaptation of Oliver Twist, even if Oliver! is a musical. Nonetheless, this is a sturdy big-screen entertainment from director Carol Reed, who will always be better remembered for 1949’s The Third Man, an all-time noir starring Joseph Cotten and Orson Welles.
Often cited as the worst Best Picture winner of the last 20 years, Crash is mildly funny, mostly for the scene in which two crooks (Chris “Ludacris” Bridges and Larenz Tate) try to carjack a Hollywood director (Terrence Howard), the burglary going spectacularly wrong. But that’s about it in terms of laughs for a film that mostly wants to remind people that racism is bad.
Chariots of Fire (1981)
The 1924 Olympics serve as the backdrop for this surprise Oscar-winner, with director Hugh Hudson more concerned with celebrating his dedicated runners (Ben Cross, Ian Charleson) than trying to crack jokes. As a result, Chariots of Fire remains among the most inspiring of all sports movies. And the theme music you know by heart.
The Sound of Music (1965)
Christopher Plummer was famously dismissive of one of his most beloved films. “It was so awful and sentimental and gooey,” he once said of The Sound of Music. “You had to work terribly hard to try and infuse some minuscule bit of humor into it.” To be sure, this musical’s dated aspects often generate unintended laughs, although with Julie Andrews around, the movie is hardly a dire affair.
Gone With the Wind (1939)
The king of problematic Hollywood classics, Gone With the Wind is the spectacle to end all spectacles: a sprawling, sentimental, swooning Civil War romance that has plenty about it that hasn’t held up. That also applies to the film’s humor, which tends toward the musty and corny.
No one expects a lot of humor from subject matter so somber. And yet, director Tom McCarthy managed to create a few wry laughs from his team of dogged investigative reporters, whose don’t-give-a-shit attitude in the face of such unimaginable evil could be bleakly funny.
The Hurt Locker (2009)
Jeremy Renner made his breakthrough with this Iraq War drama, playing a bomb defuser whose nonchalance about his dangerous work startles and unnerves everyone around him. The Hurt Locker generates its occasional laughs from the audacity of the man’s worldview, but the dark humor quickly gives way to heartbreak once it’s clear how much he needs the battlefield — ironically, nowhere else in the world feels as safe to him.
From Here to Eternity (1953)
Based on the popular James Jones novel, From Here to Eternity chronicles the buildup to the Pearl Harbor attack, looking at a group of soldiers and others in Hawaii going through their own personal dramas. Who would expect comedy from such a film? But then again, Michael Bay’s Pearl Harbor was unintentionally hilarious.
On the Waterfront (1954)
Marlon Brando electrified as Terry, the tortured dock worker who could have been a contender, in this stark drama. On the Waterfront is powerful and devastating — and not really trying to be that funny.
Midnight Cowboy (1969)
This movie’s most famous line — Dustin Hoffman’s Ratso yelling “I’m walkin’ here!” — has become so imitated and parodied that it may give the unsuspecting the impression that Midnight Cowboy is some kind of dark comedy. Far from it: This is a sad study of two men trying to survive in New York City. (Jon Voight plays would-be gigolo Joe Buck.) These guys will break your heart.
Clint Eastwood’s revisionist Western is an often bleak look at the desperate men who ruled the frontier with guns and cruelty. Anybody who tries to laugh at Unforgiven would catch a bullet from these nasty varmints.
This intimate drama, starring Ernest Borgnine as a lovelorn butcher who falls for a kindhearted teacher (Betsy Blair), captures the poetry of everyday lives. Written by Paddy Chayefsky, Marty doesn’t go for much humor — if you’re looking for caustic laughs from him, try his media satire Network.
Lawrence of Arabia (1962)
One of the great historical dramas, David Lean’s portrait of the enigmatic T.E. Lawrence was galvanized by Peter O’Toole’s stunning performance, which follows Lawrence as he goes from callow young man to disillusioned leader. There are pockets of humor in Lawrence of Arabia, but it’s but one texture in a film that remains an arresting examination of destiny and power.
World-class filmmaker that he is, James Cameron has never been the funniest guy. That’s especially true with Titanic, an epic, tragic love story that grinds to a halt when the characters try to crack jokes. Not that anybody minds: Everyone’s too busy being blown away by the sheer scope of this Oscar-winning juggernaut.
Rain Man (1988)
It’s hard to judge the humor of this Dustin Hoffman/Tom Cruise road picture today. At the time, Rain Man was a heartfelt comedy-drama about an autistic savant and his cynical, opportunistic brother, with Hoffman praised for his “transformation.” This odd-couple pairing has amusing moments, even if the whole film feels fairly cringey today.
Million Dollar Baby (2004)
This stripped-down boxing drama has the occasional funny moment as a scrappy upstart boxer (Hilary Swank) mixes it up with her cranky old trainer (director Clint Eastwood). But Million Dollar Baby is mostly going for tears during a third-act twist that found even Eastwood, one of Hollywood’s most stoic actors, getting blubbery by the end.
Grand Hotel (1932)
Directed by Edmund Goulding, Grand Hotel is part of a grand tradition of works of fiction in which a bunch of disparate characters are all in the same location at the same time, each of them dealing with their own little ordeals. The film takes place at the titular Berlin hotel, with a cast that includes Greta Garbo, John Barrymore, Joan Crawford and Lionel Barrymore. Grand Hotel doesn’t have a great reputation, although there is humor mixed in with the soap-opera-ish theatrics.
Dances With Wolves (1990)
An earnest tribute to Indigenous people, Dances With Wolves is a well-meaning, fairly toothless Western. Not surprisingly, it’s only mildly funny, too. Perhaps the best line comes not from the film, but from critic Pauline Kael’s pan: “(Kevin) Costner has feathers in his hair and feathers in his head.”
West Side Story (1961)
Neither the Sharks nor the Jets were very funny.
The Great Ziegfeld (1936)
William Powell plays Florenz Ziegfeld Jr., who made his name as a theater producer. The Great Ziegfeld isn’t considered so great, but this lavish three-hour biopic has its occasional comedic moments.
The Shape of Water (2017)
Guillermo del Toro’s Cold War romantic drama is most famous for its fantastical element — which was quickly reduced to “Wait, Sally Hawkins has sex with a fish?” But this opposites-attract love story generated laughs from its unlikely scenario.
The French Connection (1971)
Maybe not the most ha-ha hilarious movie, The French Connection’s no-bullshit characters are nonetheless funny in their own way. Plus, the film’s indelible car chase is so great you might catch yourself laughing at its sheer audacious brilliance.
The English Patient (1996)
Seinfeld mocked it mercilessly, partly because this doomed love story does take itself a bit seriously. Still, The English Patient is a sumptuous old-school drama that harks back to Hollywood’s golden age, even if its humor tends to be of the stiff-upper-lip variety.
The Lost Weekend (1945)
A story about a desperate alcoholic (Ray Milland) doesn’t sound all that humorous, but while The Lost Weekend is mostly despairing, director and co-writer Billy Wilder still managed to wring some dark humor out of this drunk’s dilemma.
As Fern, the stoic widow in director Chloé Zhao’s adaptation of Jessica Bruder’s book, Frances McDormand has some wry one-liners about her nomadic lifestyle. But Nomadland’s principal mood is that of wistful melancholy as we meet a series of rugged individualists charting their own course. The laughs are rough-hewed.
Driving Miss Daisy (1989)
Morgan Freeman drives snooty Jessica Tandy around, and the sparks fly! Driving Miss Daisy is often ridiculed for its simplistic portrayal of race relations, but these two superb actors do have some amusing moments together.
Green Book (2018)
Hey, Viggo Mortensen folds a pizza in half and eats it. That’s pretty funny, right?
Slumdog Millionaire (2008)
A plucky underdog story, Danny Boyle’s drama about a poor Indian kid (Dev Patel) courting his true love (Freida Pinto) was elevated by its vivid cinematography and buoyant soundtrack. But there’s humor in it, too, with the kid’s appearance on Who Wants to Be a Millionaire? inexplicably thematically linked to different chapters in his life, each question an aspect of his upbringing.
The King’s Speech (2010)
You think you’ve got problems? Imagine being the new King of England just as Germany is starting to cause problems on the world stage in 1939. Oh, and you have a stammer and have to address a fearful nation. Colin Firth made for an endearingly modest King George VI, with Geoffrey Rush as his tough-love speech therapist. Seen from a certain perspective, The King’s Speech is an unlikely buddy comedy between those two men — except the stakes are the fate of the free world.
The Lord of the Rings: The Return of the King (2003)
Look, there are whole posts dedicated to chronicling the funny parts of the final installment of the acclaimed trilogy. That said, what most people remember about The Return of the King is its epic grandeur, not necessarily its side-splitting moments.
An imposing biopic, Patton is a film that both celebrates its subject, General George S. Patton, and questions this country’s penchant for romanticizing war heroes. It’s not an outright satire, but George C. Scott cannily embodies the duality of this rah-rah figure, constantly asking us if this man is inspiring or merely out for himself. As a result, Patton is slyly satirical while simultaneously being undeniably rousing. All of that is embodied in its iconic opening scene.
Was Sylvester Stallone ever more charming than he was here? Soon to be better known for action spectacle, he first broke through with this disarming story of a local loser who gets a shot at the title. Stallone played Rocky as an unassuming sweetheart, a guy who was just naturally funny without trying to be. Rocky was corny, but it was a good kind of corny.
The Godfather Part II (1974)
This second chapter in the Godfather trilogy explores the Corleone family even more deeply than the first, with Francis Ford Coppola flashing back to Vito’s (Robert De Niro) youth while chronicling Michael’s (Al Pacino) ascension. There’s humor here in how these mobsters represent a twisted take on the American dream, but you wouldn’t want to risk laughing at these dangerous men.
The Godfather (1972)
A notch better, and also funnier, than its decorated sequel, The Godfather gets its laughs from bitter ironies. No, this is not a “respectable” family — they’re really just a bunch of killers. As for Michael’s potentially inspirational coming-of-age story, it only results in him becoming evil and shut off from the rest of the world. The film inspired a million parodies, but the original is absolutely no joke.
American Beauty (1999)
Director Sam Mendes and writer Alan Ball won Oscars satirizing the suburbs. Sure, some of American Beauty felt trenchant, but it also seemed fairly obvious, taking aim at easy targets. Kevin Spacey trying to get buff remains amusing, though.
Around the World in 80 Days (1956)
If we were ranking these movies by most comedy, Around the World in 80 Days would probably be No. 1. A globe-trotting adventure, based on the Jules Verne novel, the film was hailed at the time for its ambitious location shooting and its ridiculous amount of star-studded cameos. (Edward R. Murrow! Noël Coward! Frank Sinatra! Buster Keaton!) It’s also fairly zany in its “Let’s give ‘em a spectacle!” ebullience. But perhaps 80 Days’ most lasting contribution was its platform for Mexican funnyman Cantinflas, whom Charles Chaplin reportedly called the “greatest comedian alive.”
The Artist (2011)
Look, I like silent comedies, too, Michel Hazanavicius. But you don’t see me making a whole movie about it.
Going My Way (1944)
Bing Crosby plays a young progressive priest. Barry Fitzgerald plays a more traditional priest who’s not happy with this irreverent newcomer coming to his church and trying to change things. Going My Way was a crowd-pleaser that generated plenty of laughs from these two characters’ bumping of heads. Plus, it showcased Crosby’s star power: He didn’t sing as much as he did in his previous hits, but his inherent likability was undeniable.
Forrest Gump (1994)
A not-very-bright young man inexplicably finds himself again and again intersecting with the most important moments in history: That’s Forrest Gump’s central joke, which is repeated over and over to mostly successful effect, resulting in a commercial blockbuster that also won a slew of Oscars. Whether you sneer at the Boomer humor is up to you, but this ironic retelling of the history of the 1960s and 1970s is joke-laden, even if not all of them land.
Writer-director Sian Heder’s comedy-drama is focused on a Massachusetts family in which the parents and one of the two siblings is Deaf, but it’s a testament to CODA that the film never treats its characters in a precious, patronizing way. Instead, Marlee Matlin and Troy Kotsur are hilariously bawdy as the horny, messy mom and dad.
Ben Affleck’s Oscar-winner had a killer true-life premise: In the midst of the Iran hostage crisis, the U.S. government rescued its countrymen and women by sending in Americans posing as filmmakers working on a sci-fi flick. With great supporting performances from Alan Arkin and John Goodman, Argo’s truth-is-stranger-than-fiction tale generated numerous laughs from the absurdity of the CIA’s plan — which was even funnier because it actually worked.
The Sting (1973)
A lighthearted caper, The Sting reunited Butch Cassidy and the Sundance Kid stars Paul Newman and Robert Redford for a Great Depression-era film in which they play conmen out to get revenge on a malicious gangster (Robert Shaw). Although sometimes too cutesy for its own good, the film delivers plenty of laidback laughs as Newman and Redford flex their effortless charm.
Tom Jones (1963)
Madcap and hip, Tom Jones took a 214-year-old novel, starring Albert Finney as the libidinous young man seeking adventure, and made it feel utterly modern. “I have shot it all as if it were happening today,” director Tony Richardson once said, which might explain why this period comedy still feels so witty, sexy and fresh.
The Silence of the Lambs (1991)
Like many villains, Hannibal Lecter spikes his menace with dark humor. It’s one of the reasons Anthony Hopkins won Best Actor for The Silence of the Lambs, letting the character lord his intellectual superiority over everyone around him. You loathed Lecter, but you also had to admit the guy had a devilish comedic streak — when he wasn’t murdering people, of course.
The movie that resurrected the Hollywood musical, Chicago features funny performances from Renée Zellweger, Catherine Zeta-Jones and Richard Gere, each of whom is playing a schemer of one kind or another. Even the musical numbers are often pretty witty, combining electric choreography with smart visual humor.
No Country for Old Men (2007)
Even the darkest of the Coen brothers’ movies are funny, so although No Country for Old Men is about a savage assassin (Javier Bardem) hunting down a luckless cowboy (Josh Brolin) who’s made off with stolen money, there’s plenty of shocking laughs along the way. Whether it’s Bardem’s creepy, inexplicable accent or the quirky side characters we meet along the journey, this movie finds its humor in the strangest places.
Shakespeare in Love (1998)
In this delightful romantic comedy, William Shakespeare (Joseph Fiennes) falls in love with Viola de Lesseps (Gwyneth Paltrow), a free spirit who gives him the creative fuel to write his masterpiece, Romeo and Juliet. Shakespeare in Love has a blast imagining this fictional scenario, but the film’s best joke remains the aborted original title for Bill’s play. Then again, maybe Romeo and Ethel, the Pirate’s Daughter might have been great?
Birdman or (The Unexpected Virtue of Ignorance) (2014)
Those who hated director Alejandro González Iñárritu’s portrait of a washed-up actor (Michael Keaton) trying to regain his artistic credibility by starring in a Broadway play thought it was too self-aggrandizing. Me, I enjoyed Birdman’s skewering of pretensions, which is amplified by Keaton’s superb performance full of wit and sarcasm. He never lets us forget that he knows this has-been is grasping at straws, making his delusions of grandeur both pathetic and hilarious.
The Bridge on the River Kwai (1957)
Not just a great war film, The Bridge on the River Kwai is consistently sardonically funny, starting with Alec Guinness’ stubborn Lt. Colonel Nicholson squaring off with Sessue Hayakawa’s equally hardheaded Colonel Saito. Carl Foreman and Michael Wilson’s screenplay populates the story with sharp characters, including William Holden, who’s great as an American POW with a sarcastic remark for every occasion. Of course, The Bridge on the River Kwai ultimately builds to a moment of great suspense and sustained action, but before then the movie can be read as a wry commentary on the ego and delusion that go into war.
You Can’t Take It With You (1938)
One of the few true-blue comedies on this list, You Can’t Take It With You was adapted from the hit Broadway play, casting James Stewart as a member of a rich, stuck-up family who falls for a gal (Jean Arthur) from a more modest clan that’s super-quirky. When these two mismatched clans meet, hilarity does in fact ensue. Now considered a bit square and sentimental — its message is “Hey, it takes all kinds to make this crazy world go ‘round” — the film has retained plenty of its charm.
Terms of Endearment (1983)
Writer-director James L. Brooks’ feature debut is sometimes maligned for being a sappy tearjerker. But that only happens later in the film: Before then, Terms of Endearment is quite often a funny portrait of a mother (Shirley MacLaine) and daughter (Debra Winger) who are constantly at war with one another. Brooks, the man behind Taxi and (later) The Simpsons, made a big-screen comedy that didn’t feel sitcom-y, only to then waylay you with tragedy in the movie’s second half. That all said, yes, his follow-up film, the Oscar-nominated Broadcast News, is his comedic masterpiece.
One Flew Over the Cuckoo’s Nest (1975)
A film that captured the anarchic spirit of the times, One Flew Over the Cuckoo’s Nest helped establish Jack Nicholson as one of the New Hollywood’s most charismatic rebels. His Randle McMurphy was a classic antihero, gleefully standing up to mean old Nurse Ratched (Louise Fletcher), who’s trying to keep order in this mental institution. Flipping the bird to the establishment, Cuckoo’s Nest is a wicked delight — that is, until McMurphy finds out what happens to rebels.
An American in Paris (1951)
A year later, Gene Kelly would top himself with Singin’ in the Rain, one of the funniest movies ever made — not to mention a stone-cold classic. But unlike Singin’, An American in Paris won Best Picture, starring Kelly as an aspiring painter finding love and inspiration in the City of Lights. Kelly’s mega-watt charm is evident throughout, as are his underrated gifts as an ace comic actor.
My Fair Lady (1964)
One of four musicals to win Best Picture in the 1960s, My Fair Lady is the funniest, a lighthearted and sumptuous big-screen redo of the hit Broadway show, which itself was adapted from George Bernard Shaw’s Pygmalion. Audrey Hepburn is a perfect Eliza Doolittle, Rex Harrison is a dashing Henry Higgins, and the laughs are as numerous as the indelible songs.
Anyone who accuses this movie of being stuffy has clearly never seen it. Amadeus may possess all the trappings of a turgid period drama, but in fact it’s a biting satire about ambition and fate starring F. Murray Abraham as Antonio Salieri, an acclaimed composer in his day destined to be forgotten because he’s living at the same time as the mighty upstart Wolfgang Amadeus Mozart (Tom Hulce). Quickly realizing that the kid’s a genius, Salieri does everything in his power to undermine him, resulting in plenty of darkly funny scenes. To be sure, Amadeus is principally a drama, but Peter Shaffer’s screenplay (based on his acclaimed play) draws blood in its portrayal of a little man who can’t bear being usurped by a brilliant newcomer.
The Departed (2006)
Martin Scorsese’s only film to win Best Picture, The Departed often gets dinged because it’s not as great as classics like Raging Bull and Goodfellas. But here’s the thing: It’s still pretty great, and it’s really funny. This epic crime saga is filled with characters talking shit to one another, with Jack Nicholson, Matt Damon, Leonardo DiCaprio, Mark Wahlberg and Alec Baldwin engaging in the greatest dick-measuring competition of all time. The profane one-liners never stop, and even the death scenes are grimly hilarious.
Greatest cinematic love story? Best Humphrey Bogart movie ever? Most quotable film of all time? Wherever you rank Casablanca, don’t forget to throw in that it’s also damn funny. (If you ever get the chance to see it on the big screen, do it: You’ll be amazed how well it plays with a crowd, the one-liners practically bouncing off the walls.) Writers Julius J. Epstein, Philip G. Epstein and Howard Koch make Rick’s journey from bitter cynic to brave member of the resistance stirring, but they also supplied Bogie with plenty of great wisecracks — as they did with co-stars Claude Rains and Sydney Greenstreet. Every quip is delivered with tough-guy bravado. Casablanca’s wondrously wry sense of humor is another reason this movie is just plain wonderful.
It Happened One Night (1934)
Perhaps the greatest of all screwball comedies, It Happened One Night was scandalously sexy for its time, with Clark Gable and Claudette Colbert’s chemistry undeniable. Witty and clever, and filled with sparkling dialogue, this sophisticated love story masterminded a simple idea, which is that pairing a roguish journalist with a spoiled heiress can be really funny if the two leads are both beautiful and sharp. For decades since, romantic comedies have chased after what It Happened One Night made seem so effortless.
Director Bong Joon Ho decided to make a story about an impoverished family in South Korea that weasels its way into the lives of a rich family. Even better, he decided to do it as a dark comedy. Bong has often been able to weave humor into his tense, serious dramas, but with Parasite he crafted an ace satire that doubled as a moving portrait of how money (or lack of it) can destroy people. Of all the fuck-the-wealthy films of the 21st century, this one is the funniest — and also the best.
Annie Hall (1977)
Long considered the highwater mark of sophisticated romantic comedies, Annie Hall may not be as funny line-for-line as earlier Woody Allen films. Nonetheless, it’s stacked with great jokes. The subtitles reflecting what the characters are thinking while making chitchat. The snide knocks on Los Angeles’ vacuous culture. “Jew eat?” It’s all here, plus Diane Keaton’s all-timer performance as Annie Hall, who’s just as funny as her co-star.
All About Eve (1950)
No movie on this list better illustrates the principle that dramas can still be incredibly funny. The story of an aspiring theater actress who deviously attaches herself to an aging star to further her own ambitions, Joseph L. Mankiewicz’s All About Eve is a serious look at ego and art, filled with terrific performances from the likes of Anne Baxter, Bette Davis and George Sanders. And on top of all that, it’s remarkably, stunningly hilarious, the snide characters tearing into each other one quip at a time. Fasten your seatbelts for one of the all-time best Broadway takedowns.
The Apartment (1960)
Is this Billy Wilder’s funniest film? Probably not: Some Like It Hot probably bests it. But The Apartment is a wry, wise, just straight-up terrific comedy-drama in which insurance employee Bud (Jack Lemmon) agrees to lend his apartment to his male bosses so they can use it to have dalliances with their mistresses. One of those women is Fran (Shirley MacLaine), who operates the elevator in Bud’s office building and ends up bonding with this melancholy soul. (Heck, she’s a melancholy soul, too.) Lemmon and MacLaine are both terrifically funny, although it would be limiting to call The Apartment “just” a comedy. It’s one of the great movies, period — albeit one with a ton of laughs.