These are the silliest movies we’ve ever seen — and we mean that as a compliment.
If you’re having a bad day and need to clear your head — or you’re having a great day and want to make it even better — look no further than this list right here. Sometimes the silliest movies are the best movies.
Master of Disguise (2002)
“Am I not turtley enough for the turtle club?”
This hilariously absurd Dana Carvey comedy is basically just a bunch of different sketches rolled into one movie about a strange little man who has the ability to transform (almost) seamlessly into anyone by putting on disguises.
Master of Disguise may have been received quite critically when it came out, but this reporter still finds it absolutely hilarious. The ones who get it, get it, and the ones who don’t, don’t.
Keanu (2016)
Jordan Peele and Keegan-Michael Key play a pair of cousins who infiltrate a gang as part of a mission to retrieve a stolen kitten.
The buddy comedy was Key and Peele’s line movie together after their brilliant sketch comedy show Key & Peele. The rest of the cast includes Tiffany Haddish, Will Forte, Method Man and Nia Long.
There’s also a surprise cameo and we bet you can guess who it is. Whoa.
Dumb and Dumber (1994)
Jim Carrey and Jeff Daniels are unforgettably hilarious as the bumbling duo Lloyd Christmas and Harry Dunne, who go on a quest to return a suitcase full of money that they don’t realize will get them embroiled in a kidnapping.
One of the funniest, silliest lines comes when Lloyd and Harry encounter a police office on the road who tells them to “pull over.”
Harry replies: “No, it’s a cardigan, but that’s for noticing!”
Top Secret! (1984)
How silly can you get? This, one of the silliest movies of all, asks that question again and again —including in a song called “How Silly Can You Get?” sung by the great Val Kilmer as his goofy best.
Kilmer plays American rock and roll singer Nick Rivers, who gets caught up in an underground resistance movement when he falls for a beautiful woman while on tour in Germany.
Parodying both Elvis movie musicals and WWII spy films, it was the movie that David Zucker, Jim Abrahams and David Zucker made after Airplane!
Shrek (2001)
This animated comedy classic stars Mike Myers and Eddie Murphy in voice roles as Shrek the ogre and Donkey the, well, Donkey.
The peace of Shrek’s swamp is interrupted when a bunch of fairy tale folk infiltrate it after being banished by Lord Farquaad (John Lithgow). So Shrek makes a deal to rescue Princess Fiona (Cameron Diaz), who is set to be Farquaad’s bride.
There are so many hilariously quotable lines from this, so we’ll just go with a classic: “Get out of my swamp!”
Caddyshack (1980)
This hilarious and iconic golf comedy stars Chevy Chase, Rodney Dangerfield, Ted Knight, Michael O’Keefe and Bill Murray.
Caddyshack follows O’Keefe as Danny Noonan, a high school teenager working as a golf caddy at a snobby country club and trying to raise money for college.
“You’re not being the ball, Danny.”
School of Rock (2003)
This movie is so sickeningly funny that it might make you come down with a case of Stickittothemaneosis.
Following Jack Black as a washed-up rocker who steals his roommate’s identity to make some extra cash as a substitute teacher at a fancy prep school, we’d definitely consider it one of the silliest movies ever, just for Jack Black’s school teacher antics alone.
But honestly, some of the movie’s best and funniest lines come from the kids who play his students, like the iconic line spoken by Brian Falduto as Billy “Fancy Pants”: “You’re tacky and I hate you.”
I’m Gonna Git You Sucka (1988)
This blaxploitation parody movie was Keenen Ivory Wayans’ directorial debut.
Wayans stars in the film as Jack Spade, who returns home to Any Ghetto, U.S.A. after his brother tragically overdoses on gold chains. After seeing what gold chains have done to his neighbhorhood, he decides to dismantle the empire of Mr. Big (no, not that one).
We’ll never not laugh at the aquarium shoes or a very young Chris Rock negotiating for one rib.
Monty Python and the Holy Grail (1975)
Who could forget all the iconic moments in Monty Python and the Holy Grail, one of the all-time silliest movies we know?
From the Knights Who Say “Ni!” to the killer bunny, there’s no shortage of iconic moments in the 1975 classic. It starred all the members of the famous British comedy troupe: John Cleese, Terry Jones, Eric Idle, Terry Gilliam, Graham Chapman, and Michael Palin.
When in doubt, remember: “It’s just a flesh wound!”
Billy Madison (1995)
If this movie doesn’t make you smile, we don’t know what will.
Among the silliest movies ever is Billy Madison. It stars Adam Sandler as Billy, a man-child whose father challenges him to go back to grade school and pass all his classes on his own — or risk being booted from the family business.
This movie is such a gem. “For the love of God, cherish it!”
Beetlejuice (1988)
“It’s showtime!”
What movie is weirder or sillier than Beetlejuice?
Starring Michael Keaton as a trickster spirit who tries to trick Winona Ryder’s teenage Lydia into marrying him, this movie is hysterical and it just never gets old.
Now is a great time to rewatch it, considering that the sequel, Beetlejuice Beetlejuice, is set to come out in September.
White Chicks (2004)
This hysterical and iconic comedy stars Marlon Wayans and Shawn Wayans as a pair of FBI agent brothers who pose as two white women in order to lure a kidnapper they’re trying to catch.
Iconically, they dress up as the titular white chicks in full drag, resulting in one of the funniest and silliest movies we’ve ever seen.
The comedy also stars Terry Crews and Busy Philipps.
Ace Ventura: Pet Detective (1994)
Who doesn’t love Ace Ventura?
This mystery comedy stars Jim Carrey as the titular pet detective, who is tasked with tracking down a missing dolphin.
Along the way, he gets into all kinds of hysterical shenanigans, as only Jim Carrey can. Don’t be a “lew-who, za-her” — give this one a rewatch.
Anchorman: The Legend of Ron Burgundy (2004)
Will Ferrell’s iconic Anchorman character Ron Burgundy recently made an appearance at Netflix’s The Roast of Tom Brady. In full costume and character as Burgundy, Ferrell dropped some of the funniest jokes of the night.
If you need a refresher on why Anchorman is so funny, we encourage you to watch it again. And if you’ve never seen it, you’re in for a treat. Also starring Paul Rudd, Steve Carrell and Christina Applegate, it’s truly one of the silliest movies we’ve ever seen.
Bottoms (2023)
“Could the ugly, untalented gays please report to the principal’s office?”
Bringing it back to the modern day, here’s a hilarious new film that will likely be remembered for many years on.
Starring Rachel Sennott and Ayo Edebiri as a pair of high school best friends, they start a fight club in order to meet girls in the hopes of losing their virginities. But things take a turn when the popular kids take the fight club a little too seriously.
Liked This List of 15 Silliest Movies We’ve Ever Seen?
You might also like this list of the 12 Best Sitcom Casts of All Time or this list of the 18 Best Comedy Movies on Max Right Now.
Editor’s Note: Corrects main image and formatting.
Share: