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The 20 Funniest Movies of the Past 50 Years
Belly laughs, guaranteed. From 1980s classics like ‘Airplane!’ and ‘Tootsie’ to more recent gems like the new ‘Naked Gun,’ here are 20 movies that prove funny never goes out of style
Get your LOL on with these comedies, including "Barb & Star Go to Vista Del Mar," "Coming to America," "The Naked Gun" and more.
Lionsgate/Entertainment Pictures/Alamy Stock Photo; AJ Pics/Alamy Stock Photo; Moviestore Collection Ltd/Alamy Stock Photo; Pictorial Press Ltd/Alamy Stock Photo; RGR Collection/Alamy Stock Photo
When was the last time a movie made you laugh? Really laugh. We’re not talking about a tiny little chuckle or a stealthy tee-hee, but an all-out, grab-your-belly giggle fit. It’s probably been a while, right? Well, we’ve got just the cure for that. Every film on this list is guaranteed to get you rolling in the aisles. Because sometimes we all just need a good laugh.
The Naked Gun (2025, PG-13)
Who knew Liam Neeson could do slapstick this well? The Irish star took a break from a string of violent vengeance thrillers to let loose and play Frank Drebin Jr. in this gag-filled remake of the wonderfully lowbrow comedy franchise originally starring Leslie Nielsen. Just like in its predecessor, the sight gags and throwaway one-liners come at a fast and furious clip, and Neeson sells them like a pro. The plot — about a tech mogul with a nefarious scheme — is totally beside the point. The main attraction here is watching Neeson and a supremely game Pamela Anderson leave a trail of giddy mayhem in their wake.
Peak LOL moment: Neeson’s Drebin having gastrointestinal distress in his car without knowing that he’s on camera
Watch it: The Naked Gun
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Barb & Star Go to Vista Del Mar (2021, PG-13)
Get out your tropical-print caftans and capri pants, the gals are headed on a holiday! Kristen Wiig and Annie Mumolo play two middle-aged besties from small-town Nebraska who lace up their sensible shoes, pack their resort wear and head to Florida for their first-ever vacation after losing their jobs. But they’re so overwhelmed by the sunny newness of their surroundings that they fail to notice they’ve just wandered into the plot of a spy movie. A good-natured laugh riot.
Peak LOL moment: An absurd narrating crab voiced by Morgan Freeman
Watch it: Barb & Star Go to Vista Del Mar
In Bruges (2008, R)
This is a darker comedy than the other titles on this list. Which makes sense, since it’s about two Irish hit men (Colin Farrell and Brendan Gleeson) hiding out in the picturesque, medieval Belgian town of the title awaiting orders from their hot-headed crime boss (Ralph Fiennes) after an assignment goes wrong. The dialogue is razor sharp and the two leads are hilariously mismatched. The humor in this underseen gem is of a more absurd, life-is-strange variety, but somehow that makes it land with more power.
Peak LOL moment: Anytime Fiennes launches into one of his short-fused, obscenity-fueled outbursts
Watch it: In Bruges
Anchorman: The Legend of Ron Burgundy (2004, PG-13)
Will Ferrell’s career consists of playing a menagerie of clueless blowhards who are funny because they’re not aware that they’re clueless or blowhards. Still, ’70s San Diego newsreader Ron Burgundy is the best of the breed. He’s like Ted Baxter crossed with Burt Reynolds, but he thinks he’s Hugh Hefner. The Me Decade setting lends itself to fashion sight gags, Neanderthal chauvinism and cringey quips. Thanks to costars Paul Rudd, Steve Carell, David Koechner, Christina Applegate and Fred Willard, Anchorman feels like the kind of film that was a blast to make — and is even more fun to watch over and over again.
Peak LOL moment: The rival news teams’ West Side Story–esque rumble sequence
Watch it: Anchorman: The Legend of Ron Burgundy
Best in Show (2000, PG-13)
We all know how ridiculous dog owners can be. Or at least we thought we did until Christopher Guest came along with his most inspired (and delirious) mockumentary to date. Chronicling a sprawling group of eccentric, canine-loving contestants (and their purebred dogs) competing in the fictional annual Mayflower Kennel Club Dog Show, the movie is a who’s who of improv giants at the top of their game: Eugene Levy, Catherine O’Hara, Fred Willard, Jane Lynch, Michael McKean and Jennifer Coolidge. Watch in awe as these actors just make it up on the fly and let the gags rip.
Peak LOL moment: Willard as the oblivious contest announcer, Buck Laughlin
Watch it: Best in Show
The Big Lebowski (1998, R)
“Sometimes there’s a man — well, he’s the man for his time and place. ” And in this 7-10 split of a comedy from the Coen brothers, that man is Jeff Lebowski, a.k.a. the Dude. Or El Duderino, if you’re not into the whole brevity thing. A dazed and confused Jeff Bridges plays the caper’s aging hippie hero, who divides his aimless days between bowling with his pals — short-fused Vietnam vet Walter (John Goodman) and dim bulb Donny (Steve Buscemi) — and tracking down the thugs who urinated on his rug (don’t ask, but it really tied the room together). The Coens lead these oddball characters down a series of switchbacks and dead ends, and the journey is a blast.
Peak LOL moment: John Turturro as the Dude’s purple-jumpsuited bowling rival, Jesus
Watch it: The Big Lebowski
Austin Powers: International Man of Mystery (1997, R)
Mike Myers was one of the standouts on Saturday Night Live during his tenure, and his hit comedy Wayne’s World was a solid step toward marquee stardom. But nothing on his résumé hinted at the Everest heights of surreal insanity that he reached with this send-up of swinging ’60s spy movies. As the out-of-time, “shagadelic” titular secret agent, Myers is a whirling dervish of self-delusional machismo, out to stop his longtime nemesis, Dr. Evil, who’s holding the world hostage for — wait for it — “one million dollars!”
Peak LOL moment: Dr. Evil’s speech recounting his most unusual childhood: “Summers in Rangoon, luge lessons …”
Watch it: Austin Powers: International Man of Mystery
Friday (1995, R)
Pitched somewhere between Cheech and Chong and Bill and Ted, the proudly profane Friday stars Ice Cube and Chris Tucker as a pair of best pals who spend way too much time on a porch watching the world go by. All of which may sound tedious, but it’s anything but, thanks to Tucker’s motormouthed riffing and Cube’s stone-faced straight-man routine. A medium-size success when it was first released in theaters, F. Gary Gray’s breezy, slice-of-inner-city-life comedy quickly snowballed into a cult classic for anyone into toking and talking.
Peak LOL moment: Any moment Tucker opens his mouth, but this quote will suffice: “I’m gonna get you high today, ’cause it’s Friday, you ain’t got no job … and you ain’t got s--- to do.”
Watch it: Friday
Clueless (1995, PG-13)
Jane Austen’s Emma as filtered through the coming-of-age story of a consumerist mall rat. If that sounds a bit high-minded, fear not. Writer-director Amy Heckerling’s scalpel-sharp satiric rom-com is as effortlessly put together as one of star Alicia Silverstone’s haute couture outfits. It zips along like an expensive sports car. As the seemingly ditzy heroine Cher Horowitz, Silverstone gives a tour de force performance with unexpected layers of innocence and humanity beneath all the bubbles.
Peak LOL moment: Cher’s class debate about Haitian refugees, whose situation she compares to the time she threw her father a birthday party and guests arrived without RSVP’ing
Watch it: Clueless
Groundhog Day (1993, PG)
Beneath the simple, high-concept setup of Harold Ramis’ cosmic-recurrence comedy lies a deep meditation on repeating our mistakes until we get it right and in the process becoming better versions of ourselves. Then again, you could just sit back and enjoy one of Bill Murray’s smarmiest smart-aleck performances. His misanthropic weatherman, Phil Connors, heads to Punxsutawney, Pennsylvania, to cover the titular holiday and gets ensnarled in an infinite time loop full of folksy small talk.
Peak LOL moment: Phil’s street-corner run-ins with Stephen Tobolowsky’s cloying insurance agent, Ned Ryerson. Bing!
Watch it: Groundhog Day
White Men Can’t Jump (1992, R)
Ron Shelton has given us some classic sports movies (Bull Durham, Tin Cup), but none are funnier than this odd-couple comedy about a pair of ego-driven basketball hustlers (Woody Harrelson and Wesley Snipes) who team up to fleece suckers on the court. The chemistry between Harrelson and Snipes is electric — a crackling combination of street smarts, swagger and a barrage of rat-a-tat put-downs. The punch lines hit nothing but net!
Peak LOL moment: Any time Rosie Perez (as Harrelson’s chatty girlfriend) is on screen
Watch it: White Men Can’t Jump
Defending Your Life (1991, PG)
I have no clue what the afterlife will bring, but I do hope it’s half as funny as this deliciously clever Albert Brooks comedy about a guy who dies in a car accident and wakes up in an Epcot-like limbo where he not only falls in love with Meryl Streep (who wouldn’t?), but also has to rationalize a lifetime of questionable decisions in a purgatorial courtroom. Rip Torn is gruff perfection as Brooks’ defense attorney.
Peak LOL moment: The Past Lives Pavilion, where Brooks sees himself being chased by a lion in a former life
Watch it: Defending Your Life
Midnight Run (1988, R)
Buddy action-comedies don’t come better than this odd-couple road movie starring Robert De Niro as a prickly but principled bounty hunter and Charles Grodin as the mob accountant he needs to bring cross-country on a tight deadline while eluding Mafia goons. Even with his gruff exterior, De Niro has never been looser or funnier than he is here. And Grodin, with his sour string of complaints and phobias, manages to be winning while whining.
Peak LOL moment: De Niro and Grodin impersonate FBI agents to inspect a shopkeeper’s cash register and run an improvised con called “the Litmus Configuration”
Watch it: Midnight Run
Coming to America (1988, R)
Eddie Murphy is like a kid playing dress-up in his bedroom in John Landis’ delirious fish-out-of-water comedy about a pampered African royal who travels to the inaptly named Queens to find a regal bride. With Arsenio Hall as his loyal wingman, Murphy is allowed to go wherever his genius takes him, playing a handful of hysterical alter egos under layers of makeup and wigs.
Peak LOL moment: A barely recognizable Murphy as singer Randy Watson, whose band Sexual Chocolate does an interesting cover of Whitney Houston’s “Greatest Love of All”
Watch it: Coming to America
Ferris Bueller’s Day Off (1986, PG-13)
After Sixteen Candles, The Breakfast Club and Weird Science, John Hughes hit his high point as a director with this escapist, perfectly engineered teenage fantasy about an irresistible wiseass (Matthew Broderick) who plays hooky with his best buddy, Cameron (Alan Ruck), and his sweetheart (Mia Sara) while getting to drive a Ferrari, impersonate “Sausage King of Chicago” Abe Froman and sing “Twist and Shout” on a parade float.
Peak LOL moment: Ferris and Cameron ad-libbing and bickering during a phone call to their archnemesis, Dean of Students Ed Rooney
Watch it: Ferris Bueller’s Day Off
Fletch (1985, PG)
Based on Gregory Mcdonald’s hard-boiled novel, Fletch lets Chevy Chase unleash his wicked brand of condescending charisma better than any of his other movies from his peak, ’75–’85 era. He plays a gonzo investigative reporter who gets roped into a twisty murder-for-hire plot that allows him to solve a mystery, try on a dozen loopy aliases and fire off snappy one-liners like a comedy howitzer.
Peak LOL moment: Fletch crashing a ritzy country club as a “guest” of the Underhills
Watch it: Fletch
This Is Spinal Tap (1984, R)
Rob Reiner’s arch mockumentary about a band of British heavy metal idiots could have been as broad as the side of a barn and still been funny. Instead, stars Christopher Guest, Harry Shearer and Michael McKean go for something more, nailing the smallest details, which is what turns it into a brilliant satire — right down to the song titles “Big Bottom,” “Tonight I’m Gonna Rock You Tonight” and the classical ballad “Lick My Love Pump.”
Peak LOL moment: Obviously, the amp that goes to 11
Watch it: This Is Spinal Tap
Tootsie (1982, PG)
Dustin Hoffman stars as an out-of-work New York actor who makes himself over into a sassy Southern belle named Dorothy Michaels to land a part on a hit daytime soap — and in the process stands up for women’s rights in the workplace, falls in love with Jessica Lange and fends off the advances of her smitten father (the late, great Charles Durning).
Peak LOL moment: Hoffman asking his roommate (Bill Murray) which dress looks better on him before going out. Murray’s response: “We’re getting into a weird area.”
Watch it: Tootsie
Diner (1982, R)
Writer-director Barry Levinson’s love letter to coming of age in 1950s Baltimore puts together a note-perfect ensemble of then up-and-coming actors (Daniel Stern, Steve Guttenberg, Mickey Rourke, Kevin Bacon, Timothy Daly, Paul Reiser and Ellen Barkin) and brilliantly allows them to shift between laugh-out-loud comic vignettes and poignant, unspoken truths about the fear of becoming a grownup.
Peak LOL moment: Guttenberg’s football quiz for his bride-to-be that he secretly wants her to fail
Watch it: Diner
Airplane! (1980, PG)
Shooting off the screen with a dizzying jokes-per-minute ratio, this Zucker-Abrahams-Zucker spoof of Hollywood disaster epics belongs in the Guinness Book of World Records for its sheer number of sight gags, silly puns and straight-faced one-liners. Airplane! is so dense with jokes you can watch it over and over again and still notice new bits of comic anarchy in every corner of the frame.
Peak LOL moment: Leslie Nielsen’s deadpan delivery of “I am serious … and don’t call me Shirley”
Watch it: Airplane!
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