Buzz
"Funny like how? How am I funny… like I’m a clown to you?"
Just like Joe Pesci and Ray Liotta once did, we could all use a good laugh right now – an escape from the everyday grind. Now might be the perfect time to settle in and revisit some classic comedy films. Even if not everyone agrees with all of these choices, I hope you’ll enjoy reading it as much as I enjoyed putting it together.
Here are ten of the funniest films in cinema history, listed chronologically, with one so-bad-it’s-good surprise at the end.
10. Monty Python and the Holy Grail (1975)
No, this isn’t just a flesh wound. It’s a stroke of comedic genius, making it an obvious choice for this list.
No one does the ‘morons on a mission’ bit better than Monty Python. Picture half a dozen knights hiding behind a boulder, nervously watching ‘the beast,’ which turns out to be a bunny (“That’s the most foul, cruel and bad-tempered rodent you ever set eyes on!”). Their attempts to defeat the troublesome rabbit involve using the Holy Hand Grenade of Antioch.
When the group reaches the Bridge of Death, they must answer three questions from a troll to pass. The troll starts gently with the first knight but ramps up the absurdity with questions like “What’s the capital of Assyria?” and “What is the airspeed velocity of a laden swallow?” Meanwhile, an attempt to besiege a castle is humorously thwarted with a barrage of catapulted livestock.
One reason Holy Grail is often regarded as its funniest film is that, unlike many comedies, its humor doesn’t age poorly. Set in the Middle Ages, it’s free from time-specific references that would otherwise lose their charm over the years.
9. Airplane! (1980)
Surely you didn’t think I’d leave Airplane! off this list. With a budget of just $ million – a modest sum even 40 years ago – this ensemble comedy earns my pick for the funniest film ever made.
If comedy were a boxing match, Airplane! would be a fast-flying bantamweight, landing rapid-fire jabs left and right. It’s like throwing spaghetti at a wall while shooting with a machine gun: the laughs come so quickly that you barely finish laughing before the next joke hits.
Of course, that approach only works if the jokes are sharp. From the main character’s battle with a drinking problem to an old woman helping a stewardess interpret jive, Airplane! delivers punchline after punchline so fast that you’re left breathless from all the laughter.
Airplane! also shines with its clever wordplay. When a flight attendant tells former fighter pilot Ted Striker, “there’s a problem in the cockpit,” he asks, “The cockpit? What is it?” She responds, “It’s a little room in the front of the plane, where the pilot sits.”
This technique, along with recurring gags like “I picked the wrong week to stop…,” lets Airplane! stretch a simple 15-minute plot – “Plane in danger, hijinks ensue” – into 90 minutes of nonstop comedic brilliance, putting the plot on autopilot (in more ways than one) and leaving room for the laughs.
8. Caddyshack (1980)
Any movie that pokes fun at golf – an “arrogant, elitist game which takes up entirely too much room in this country,” according to George Carlin – gets my approval. Riding the wave of Rodney Dangerfield’s crude humor, Caddyshack (1980) does so with a style that practically knocks the smarm off a country club member’s face.
As the brash, obnoxious nouveau riche character Al Czervik, Dangerfield is both a fish out of water and a bull in a china shop. After yelling “Fore!” and nailing one of his rivals in the groin with a tee shot, Dangerfield smugly quips, “I shoulda yelled two!” Later, at a stuffy party full of snooty elderly guests, he calls it “The dance of the living dead.”
The film also features two early Saturday Night Live stars. Chevy Chase excels at delivering deadpan humor as the quirky straight man. “Do you take drugs, Danny?” he asks the caddy. When Danny answers yes, Chase responds, “Good... so what’s the problem?” Meanwhile, Bill Murray takes a break from his groundskeeping duties to score a horticultural hole-in-one, teeing off on flowers while mimicking a calm TV announcer (“He got all of that one!”).
As a bonus, Caddyshack 2 (1988) turned out to be one of those rare sequels worth making. Not quite as funny as the original, but still in the same ballpark… I mean, on the same fairway.
7. The Naked Gun (1988)
No, that’s not Enrico Palazzo. It’s Leslie Nielsen again, rightfully making his second appearance on this list.
The Naked Gun, a hilarious big-screen continuation of the Police Squad! comedy series, is the finest TV-to-movie adaptation ever. The eclectic cast, including Nielsen, Ed Williams, Priscilla Presley, and a pre-alleged-double-homicide OJ Simpson, left audiences in stitches—and questioning why Police Squad! got canceled after just six episodes.
Much like Airplane!, The Naked Gun employs a rapid-fire, spaghetti-at-the-wall approach where deadpan humor, outrageous slapstick, and pure absurdity relentlessly hit the audience. Nielsen excels as the bumbling investigator, drawing parallels to Maxwell Smart.
Interestingly, while many comedies falter in their conclusion, as tying up the plot often slows down the humor, The Naked Gun delivers its finest moments at the end. The film culminates in a chaotic rendition of the Star-Spangled Banner (“And the rockets’ red glare/buncha bombs in the air”), a pregame blooper reel featuring a decapitated outfielder (“How about that?”), and Nielsen as a breakdancing umpire. The baseball game finale ranks among the funniest fifteen minutes in cinematic history.
6. National Lampoon’s Christmas Vacation (1989)
The real question wasn’t whether National Lampoon’s would make the list, but which one. I chose Christmas Vacation, which holds the title of the funniest holiday movie of all time (with a shout-out to Will Ferrell’s wild classic, Elf).
This film is loaded with so many iconic lines that it’s impossible to pick a favorite, but let’s start with Randy Quaid, who plays Ellen’s redneck cousin-in-law, dumping an RV sewage tank into a street grate while cheerfully greeting Clark’s uptight neighbor: “Merry Christmas! Shitter was full!”
Christmas Vacation might just be the most uproarious chain-reaction disaster movie ever. Clark’s elderly uncle sets the tree on fire with a cigar, a tipping point that sends Clark into a frenzy, grabbing a chainsaw and chopping down the tree in his front yard, which crashes through his neighbor’s window. He drags it inside... and a squirrel leaps out, sending Eddie’s dog, the appropriately named Snot, on a wild chase, wrecking the house. The solution? Clark opens the door, and both the squirrel and dog take a flying leap... into the arms of Julia Louis-Dreyfus, who had come over to confront Clark about the tree smashing through her window.
Christmas Vacation is one of those rare films that, even after over 30 years, never feels out of place. It remains a timeless holiday tradition, offering comfort in the face of relentless in-laws. Be grateful for it – and don’t forget to say grace. (“Grace? She passed away 30 years ago!”)
5. Austin Powers: International Man of Mystery (1997)
Yeah, baby. Mike Myers’ parody of James Bond stands out as the funniest live-action film of the 1990s (though Tommy Boy, starring the late, great Chris Farley, deserves an honorable mention).
This movie hits on so many levels – from poking fun at cheesy spy movie fight scenes (“Judo CHOP!”) to Myers’ flawless comedic character creation. But the real highlight is the “double fish out of water” concept. Myers portrays both the hero Austin Powers and his arch-nemesis, Dr. Evil, both of whom have been revived after being frozen for 30 years.
This setup adds an extra layer of cluelessness, allowing Myers’ ability to create awkwardly funny moments to shine. For instance, Dr. Evil demands a ransom of… “one MILLION dollars!” – a surprisingly low figure to stop a madman from using liquid hot magma to destroy civilization.
Practically every move Myers makes in this film is a hit. From pairing Dr. Evil with a miniature clone (“I shall call him… Mini-Me”) to introducing his right-hand woman, Frau Farbissina (“head of the militant wing of the Salvation Army”), to Austin punching an elderly woman in the face out of suspicion that she was secretly a “man, baby!”—the film consistently lands every joke. One of the funniest moments might be Dr. Evil’s frenzied rant during a father-son therapy session, recalling his childhood (“Summers in Rangoon, luge lessons… quite standard really.”)
4. South Park: Bigger, Longer & Uncut (1999)
Without a doubt, the funniest animated film ever is Trey Parker and Matt Stone’s adaptation of their boundary-pushing cartoon series, South Park. At a time when musicians like Eminem and Marilyn Manson were stirring up parental outrage, Parker and Stone decided to poke fun at both their audience and society with one of the most subversive comedies ever made.
I was in college when the film premiered, and I remember being surprised to see parents with young children in the theater, especially since it was rated R. Then it dawned on me: Parker and Stone had done this intentionally, tricking unsuspecting parents into bringing their kids. After all, how inappropriate could a cartoon possibly be?
About ten minutes into the movie, “Uncle F*cker,” the second musical number (yes, it’s a musical—a brilliantly profane one), answers that question decisively. (“Shut your f*cking face unclef*cker, you’re a c*cksucking asslicking unclef*cker…”) From that point on, a full album’s worth of riotous songs, including the Grammy-nominated “Blame Canada,” make up the funniest soundtrack in cinematic history.
The film’s plot – the South Park kids must rescue two scapegoated comedians who are about to be executed for telling fart jokes – cleverly mirrors the reaction Parker and Stone anticipated for the film. In a way, the movie both sparks controversy and addresses it head-on. And if you’re not a fan, well, Cartman has something to say to you.
3. Superbad (2007)
When considering the most recent wave of big-screen comedians, we can’t leave out Seth Rogen. While The 40-Year-Old Virgin certainly earns its place (with Paul Rudd, who’s universally adored), 2007’s Superbad edges it out, aided by an obsessively drawn penis from a young Jonah Hill.
Superbad stands out as one of the rare comedies that effortlessly juggles multiple plot twists without sacrificing its humor. The film combines storylines like trying to score alcohol for a high school graduation party, the tension between the two leads as they go their separate ways for college, adolescent crushes, and the overbearing antics of bumbling cops – all of which blend together to create a film that is both heartwarming and laugh-out-loud funny, a rare feat for R-rated comedies.
The physical humor in Superbad is especially impressive. Fogel’s obvious unease as an underage liquor store customer, paired with his awkward attempt at small talk (“Been drinking this stuff for years… I hear they’ve recently added more -twitch- hops”), is cut short by one of the most iconic face-punches ever seen on screen.
When the police arrive to question witnesses, Fogel’s fake ID with a single name raises suspicion and later sympathy, thus cementing the legendary status of McLovin’ in the annals of comedy history.
2. Borat (2006)
Officially named 'Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan,' Sacha Baron Cohen’s razor-sharp and offensive portrayal of a foreigner navigating American life stands as the most uproarious mockumentary ever (with a special shout-out to 2000’s Best in Show). Like his pioneering TV series Da Ali G Show, the brilliance of the film lies in the fact that the people being pranked have no idea they’re the butt of the joke.
In the role of Borat Sagdiyev, Cohen expertly wields America’s faux-tolerance and racial issues, making a pointed yet hilarious statement. During a dinner party, Borat hilariously displays his ignorance, not just of American culture but even basic indoor plumbing, as he hands his host a bag of his feces after using the bathroom. At a rodeo, he stirs the crowd by supporting the Iraq War with the absurd declaration, 'we support your war of terror' and hopes that 'George W. Bush drinks the blood of every man, woman and child of Iraq!'
At a honky-tonk bar, Borat delivers a song called 'In My Country There is Problem,' managing to get a group of cowboy-hat-wearing simpletons to enthusiastically sing along with the chant 'Throw the Jew Down the Well, so my country can be free!' Later, when he meets a kind Jewish couple renting out a room in their home, Cohen masterfully flips the mockery, highlighting the Middle East’s pervasive anti-Semitism by throwing money at cockroaches, which Borat believes are the shape-shifted hosts ('You could barely see their horns').
1. Anchorman: The Legend of Ron Burgundy (2004)
“I’m Ron Burgundy?”
Will Ferrell’s 2004 portrayal of a hilariously clueless and misogynistic 1970s newscaster is the crowning achievement of his comedic career – and that’s no small accomplishment. Much like Austin Powers before it, Anchorman quickly establishes itself as a ridiculous movie, but in the best possible way. It’s absurdity perfected, and that’s entirely due to Ferrell’s comedic genius. From the outrageous banter in the closing credits ('You’re a real hooker, and I’m gonna slap you in public') to Burgundy’s hilarious belief that the name of his hometown, San Diego, translates to 'whale’s vagina,' Ferrell’s delivery is nothing less than brilliant.
The film’s infamous newscaster showdown is what truly secures Anchorman’s spot among the greatest comedies. Featuring Tim Robbins as a public access newsman ('No commercials… no mercy!'), the wild street brawl is nothing short of mayhem – Luke Wilson gets his arm severed by a machete while Brick Tamland (Steve Carell), the lovable but dim-witted weatherman, defeats an opponent on horseback with a trident. 'Boy,' Burgundy comments the next day to his team, 'that escalated quickly.'
Still not convinced Anchorman deserves its place on this list? Well, then go f*ck yourself, San Diego.
+ The Room (2003)
“It’s ‘The Room’ bad.”
This was the reaction from a film industry friend to the 2019 movie Cats, which earned a reputation as one of the worst movies ever made.
2003’s The Room – a film that was written, directed by, and starred the eccentric, often hard-to-understand Tommy Wiseau, who poured millions of his own money into making it – became infamous for being so bad (and so weird) that it developed a massive cult following (complete with a talking bobblehead) and even inspired a successful movie about its creation, 2017’s The Disaster Artist.
It’s gloriously awful. The dialogue features some truly bizarre moments, such as a character announcing she has cancer, only for it to never be mentioned again, and it feels like it was written by an AI that studied human behavior... poorly. There are also two painfully long love scenes that make you question whether Wiseau has any knowledge of basic human anatomy. And for some reason, there are pictures of spoons in the background – leading to the tradition of throwing silverware during midnight showings.
“So what?,” you might think. “A lot of movies are terrible.” That’s true, but The Room wasn’t just mocked by Hollywood – it was absolutely destroyed by the cast of Mystery Science Theater 3000. Now called RiffTrax, the trio made a career out of roasting bad movies. Watching RiffTrax take on The Room is one of the funniest movie experiences I’ve ever had. I highly recommend it.
