“Funny like how? How am I funny… like I’m a clown to you?”
Like Joe Pesci and Ray Liotta before us, we could all use a good laugh lately – a welcome escape from our current housebound humdrums. There may never be a better time to curl up on the couch and revisit some legendary comedy films. And whether or not you agree with every entry, I hope you’ll have as many chuckles reading it as I did putting it together.
Here are ten of the funniest films in movie history, presented in chronological order with a so-bad-it’s-good wildcard at the end.
10 Monty Python and the Holy Grail (1975)
No, it’s not just a flesh wound. It’s comedic genius and a no-brainer addition to this list.
No comedy group does “morons on a mission” better than Monty Python. Half a dozen knights crouching dutifully behind a boulder, cautiously peering out at “the beast” that ends up being a bunny (“That’s the most foul, cruel and bad-tempered rodent you ever set eyes on!”). Efforts to vanquish the rascally rabbit include the Holy Hand Grenade of Antioch.
When the gang comes across the Bridge of Death, they must answer three questions from a troll to gain crossing privileges. The troll goes easy on the first knight before asking the second two easy questions followed by “What’s the capital of Assyria?” The questions get more ridiculous from there (“What is the air speed velocity of a laden swallow?”). And of course, an attempt to lay siege to a castle is viciously repelled via catapulted livestock.
One of the reasons Holy Grail is widely considered its funniest film, I believe, is that comedy often doesn’t age well. This gives an advantage to something set in the Middle Ages, eliminating decade-specific references that grow stale with time.
9 Airplane! (1980)
Surely you didn’t think I’d leave Airplane! off this list. Produced for what even 40 years ago was the astoundingly low budget of $3.5 million, the ensemble-cast laugh-fest gets my vote for funniest film ever.
If comedy were boxing, Airplane! is a lightning-fast bantamweight that peppers rapid-fire jabs. Airplane! is spaghetti at a wall shot with a machine gun: the comedy comes so fast that the audience isn’t done laughing before the next joke lands.
Of course, that recipe can only work if enough of the jokes are good. And from the main character’s drinking problem to an old lady who helps the stewardess translate jive, Airplane! is so fast and laugh-out-loud funny that it’s hard to catch your breath.
Of note, Airplane! excels at comedy welded with wordplay. When a flight attendant tells passenger and disgraced fighter pilot Ted Striker that “there’s a problem in the cockpit,” he replies “The cockpit? What is it?”, prompting her to explain that “It’s a little room in the front of the plane, where the pilot sits.”
This device, in addition to recurring jokes like “I picked the wrong week to stop…”, allows Airplane! to fill 90 minutes with a plot that could have been told in 15. “Plane in danger, hijinks ensue” is a simple way to put the plot on (a sexually satisfied) autopilot and clear the path for undistracted comedy brilliance.
8 Caddyshack (1980)
Any movie that ridicules golf – per George Carlin, an “arrogant, elitist game which takes up entirely too much room in this country” – is OK in my book. Riding Rodney Dangerfield’s boorish irreverence, 1980’s Caddyshack does so with a style that smacks the smarm right off a country club member’s face.
As brash, obnoxious nouveau riche protagonist Al Czervik, Dangerfield is both fish out of water and bull in a china shop. After yelling “Fore!” and hitting one of his antagonist’s square in the nuts with a tee shot, a self-satisfied Dangerfield declares “I shoulda yelled two!”. Later, at a posh party chock full of snooty septuagenarians, Dangerfield deems the shindig “The dance of the living dead.”
The movie also showcased two early Saturday Night Live cast members. Chevy Chase showcases his unsurpassed ability to deliver deadpan lines as an offbeat straight man. “Do you take drugs, Danny?” he asked the caddy. When Danny answers in the affirmative, Chase replies “Good.. so what’s the problem?” Meanwhile, Bill Murray takes a break from his groundskeeping duties for a horticulture hole in one, teeing off on flowers while mimicking a subdued TV announcer (“He got all of that one!”)
As a bonus, 1988’s Caddyshack 2 was one of the rare sequels worth making. Not as funny as the original, but in the same ballp… I mean, on the same fairway.
7 The Naked Gun (1988)
No, that’s not Enrico Palazzo. It’s Leslie Nielsen again, deservedly making his second appearance on this list.
A side-splitting big screen follow-up to the comedy series Police Squad!, The Naked Gun is the funniest TV-to-movie adaptation ever. The highly unorthodox foursome of Nielsen, Ed Williams, Priscilla Presley and a pre-alleged-double-homicide OJ Simpson left audiences laughing—and wondering why Police Squad! was canceled after just six episodes.
Like Airplane!, The Naked Gun has a spaghetti-at-the-wall, rapid-fire style where deadpan one liners, silly slapstick and general stupidity fly full-speed at the audience. Nielsen plays the perfect idiot protagonist—a bumbling investigator drawing parallels to Maxwell Smart.
Notably, while many comedies struggle to close a film, because the need to sew up the plot tends to pump the comedy brakes, The Naked Gun’s saves its best for last. Punctuated by a mangled Star-Spangled Banner (“And the rockets’ red glare/buncha bombs in the air”), a pregame bloopers reel featuring a decapitated outfielder (“How about that?”), and Nielsen as a breakdancing umpire, the baseball game at the film’s finale is among the funniest fifteen minutes in cinema history.
6 National Lampoon’s Christmas Vacation (1989)
The question wasn’t whether National Lampoon’s would make the cut, it was which movie. I went with Christmas Vacation, which holds the distinction of funniest holiday movie ever (honorable mention to Will Ferrell’s deranged classic, Elf).
This movie has so many quotable lines it’s impossible to know where to start, but how about Randy Quaid, playing Ellen’s white trash cousin-in-law, emptying an RV sewage tank into the street grate while waving to Clark’s uptight neighbor: “Merry Christmas! Shitter was full!”
Christmas Vacation might be the most hilarious cascading-disaster movie ever made. Clark’s elderly uncle burns down his tree with a “stogie”, a last straw that causes Clark to go berserk with a chainsaw and cut down the evergreen on his front lawn, which smashes his neighbors window as it falls. He drags it in… and a squirrel jumps out, prompting Eddie’s dog, the aptly named Snot, to chase the rodent and wreck the rest of the house. The solution? Clark opens the door and both squirrel and dog leap out… into the arms of Julia Louis-Dreyfus, who’d come over to confront Clark over the tree that has smashed through her window.
Christmas Vacation is one of those movies that, more than 30 years later, can and never will feel dated. It will be there year after year, comforting us amid a sea of annoying in-laws. Be thankful for it – and say grace. (“Grace? She passed away 30 years ago!”)
5 Austin Powers: International Man of Mystery (1997)
Yeah baby. Mike Myers’ James Bond parody was the funniest live-action movie of the 1990s (an honorable mention to Tommy Boy, starring the late great Chris Farley).
The film works on so many levels – the bad spy movie-mocking fight scenes (“Judo CHOP!”) and Myers’ impeccable comedic character development, to name just two. But perhaps the most successful element is the “double fish out of water” element. Myers plays both the protagonist Austin Powers and his archnemesis, Dr. Evil, each of whom have been reanimated after having been frozen for 30 years.
The result is an extra layer of cluelessness that allows Myers’ knack for awkward-moment hilarity to really pop; for example, Dr. Evil attempts to hold the world ransom for… “one MILLION dollars!” – a paltry price to prevent a lunatic from incinerating civilization with liquid hot magma.
Practically nothing Myers tries in this film falls flat. From pairing Dr. Evil with a clone 1/8 his size (“I shall call him… Mini-Me”) to his right-hand woman, Frau Farbissina (“head of the militant wing of the Salvation Army”) to Austin punching an old woman in the face out of suspicion she was really a “man, baby!,” the movie swings wildly and lands every punchline it throws. Its funniest scene might be Dr. Evil’s maniacal rant during a father-son therapy session, where he describes his childhood (“Summers in Rangoon, luge lessons… quite standard really.”)
4 South Park: Bigger, Longer & Uncut (1999)
By far, the funniest animated movie ever is Trey Parker and Matt Stone’s adaptation of their envelope-pushing cartoon series, South Park. At a time when musical acts like Eminem and Marilyn Manson were causing parental uproar, Parker and Stone decided to troll the audience and society at large with one of the most subversive comedies ever.
I was in college when the movie came out. Sitting in the theater, I was surprised to see parents there with little kids; after all, the movie was rated R. Then it hit me: Parker and Stone had done this on purpose, luring unsuspecting parents to take their kids. After all, how raunchy could a cartoon really be?
At about ten minutes in, “Uncle F*cker,” the movie’s second musical number (yes, it’s a musical—a brilliant, foul-mouthed musical), answers this question with authority. (“Shut your f*cking face unclef*cker, you’re a c*cksucking asslicking unclef*cker…”) From there, a full album’s worth of uproarious songs, including the Grammy-nominated “Blame Canada,” amount to the funniest soundtrack in film history.
The movie’s plot – the South Park kids must rescue a pair of scapegoated comedians from being executed for telling fart jokes – ingeniously mirrors the reception Parker and Stone knew the movie would receive. The movie, then, both causes controversy and responds to it. And if you don’t like it, well, Cartman has a message for you.
3 Anchorman: The Legend of Ron Burgundy (2004)
“I’m Ron Burgundy?”
His 2004 portrayal of a cluelessly misogynistic 1970s newscaster is the highlight of Will Ferrell’s comedic career – and that’s saying a lot. Like Austin Powers before it, you get the feeling ten minutes in that Anchorman is going to be a really stupid movie. And it is – it’s just stupidly terrific, a feat only pulled off with a fearsomely funny front man. From cheery-faced vulgar banter over the newscast’s closing credits (“You’re a real hooker, and I’m gonna slap you in public”) to wistfully musing that the name of his hometown San Diego translates to “whale’s vagina,” Ferrell’s delivery is sheer genius.
It’s the famous newscaster royal rumble, however, that puts Anchorman into the all-time top ten. Including Tim Robbins as a public access newsman (“No commercials… no mercy!”), the weapons-laden street brawl features Luke Wilson getting his arm chopped off with a machete while Brick Tamland (Steve Carell), a mentally-challenged weatherman, kills a horse-riding combatant with a trident. “Boy,” Burgundy says the next day to his team, “that escalated quickly.”
Still don’t think Anchorman belongs on this list? Then go f*ck yourself, San Diego.
2 Borat (2006)
Officially titled “Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan,” Sacha Baron Cohen’s brilliantly offensive depiction of a foreigner exploring American society is the most side-splitting mockumentary ever (honorable mention to 2000’s Best in Show). Like his groundbreaking TV series Da Ali G Show, the movie’s greatest asset is that its subjects aren’t in on the joke.
As Kazakhstan native Borat Sagdiyev, Cohen uses America’s faux-inclusion and racism against it in a way that is revealing and revolting, yet hysterical. At a dinner party, Borat pleads ignorance of not only American customs but American indoor plumbing, graciously handing the host a bag with his feces after using the restroom. At a rodeo, he declares his support for America’s controversial Iraq War by declaring – to a ravenously applauding crowd of rednecks – “we support your war of terror” and hoping “George W. Bush drinks the blood of every man, woman and child of Iraq!”
At a honky tonk, Borat performs a song called “In My Country There is Problem,” eventually getting the crowd of cowboy hat-wearing dimwits to clap and sing along to the refrain “Throw the Jew Down the Well, so my country can be free!” When he meets an actual Jewish couple – a kindly old man and wife renting a room in their home to overnight guests – Cohen flips his mockery to the Middle East’s rampant hatred of Jews by throwing money at cockroaches, whom Borat believes are his shape-shifted hosts (“You could barely see their horns”).
1 Superbad (2007)
Moving into the most recent set of big-screen comedians, we’d be remiss not to include Seth Rogan somewhere on this list. And while The 40-Year-Old Virgin gets due consideration (and has Paul Rudd – whom everyone loves), 2007’s Superbad beats it out by the tip of an obsessively-drawn penis from a grade-school Jonah Hill.
Superbad is one of the rare comedies that manages to incorporate and resolve a variety of plot twists without sacrificing the humor. Difficulty getting alcohol for a high school graduation party, tension between the two main characters as each goes to different colleges, teen get-the-girl ambitions and insecure police dickishness are A, B, C and even D stories that combine to make the film both heartwarming and side-splitting – a rarity for R-rated comedies.
Superbad’s physical humor is particularly outstanding. Fogel’s nervousness as an obviously underage liquor store customer, including his ridiculous attempt to small-talk the cashier (“Been drinking the stuff for years… I hear they’ve recently added more -twitch- hops”) is interrupted by one of the best movie face-punches ever.
When the cops show up to interview the witnesses, his single-named fake ID draws suspicion and then pity, and the legend of McLovin’ is born.
+ The Room (2003)
“It’s ‘The Room’ bad.”
That was a film industry friend of mine reacting to the 2019 movie Cats, roundly mocked as among the worst movies ever made.
2003’s The Room – written, directed by and starring the eccentric, marble-mouthed Tommy Wiseau, who invested millions of his own money to produce and release it – was so bad (and so ridiculously weird) that it sparked a cult following (including a talking bobblehead) and even a hit movie about its making, 2017’s The Disaster Artist.
It’s awesomely awful. The dialogue, whose foibles include a prominent character announcing she has cancer, then never referencing it again, seems written by a bot that studied human behavior, albeit poorly. Two awkward, waaaaay too long love scenes leave the audience wondering whether Wiseau is familiar with basic human anatomy, and for some odd reason there are pictures of spoons in the background – prompting cult followers to fling silverware during indie theater screenings.
“So what?,” you may be thinking. “Lots of movies are awful.” True, but The Room wasn’t just parodied by mainstream Hollywood: it was torn a new one by the cast of Mystery Science Theater 3000. Now called RiffTrax, the trio makes a killing from killing bad movies. Watching RiffTrax roast The Room is the funniest cinematic experience I’ve ever had. I highly recommend it.