The 20 Funniest Movies of the Last 50 Years

National Lampoon's Vacation (1983)

Chevy Chase is perfection as the tightly wound suburban dad Clark Griswold — a put-upon boob who takes his wife, two cheerless kids and dotty Aunt Edna on a cross-country road trip to visit Walleyworld, a Disney-like theme park that turns out to be closed. By that point, though, Clark has been put through the existential wringer so thoroughly that he snaps. A nonstop exercise in gut-busting humiliation.

Peak LOL moment: The barbecue at Uncle Eddie's, where Randy Quaid declares, “I don't know why they call this stuff Hamburger Helper, it does just fine by itself … “

Watch it: National Lampoon's Vacation, on Amazon Prime, Google Play, HBO Max, iTunes, Vudu, YouTube

This Is Spinal Tap (1984)

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, on Amazon Prime, iTunes, Vudu, YouTube

Fletch (1985)

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. Here 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, on Amazon Prime, Google Play, iTunes, Vudu, YouTube

Ferris Bueller's Day Off (1986)

After Sixteen Candles, The Breakfast Club and Weird Science, John Hughes reached his peak 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 high school 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 their phone call to archnemesis Principal Rooney.

Watch it: Ferris Bueller's Day Off, on Amazon Prime, Google Play, iTunes, Netflix, Vudu, YouTube

Coming to America (1988)

Eddie Murphy is like a kid playing dress-up in his bedroom on a rainy day in John Landis’ delirious fish-out-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, on Amazon Prime, Google Play, iTunes, Vudu, YouTube

Midnight Run (1988)

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, on Amazon Prime, Google Play, iTunes, Netflix, Vudu, YouTube

Groundhog Day (1993)

Beneath the simple, high-concept setup of Harold Ramis’ cosmic recurrence comedy lies a deep meditation on repeating our mistakes until we get them right, and in the process, become better versions of ourselves. Then again, you could just sit back and watch it as one of Bill Murray's smarmiest smart-aleck performances, where his misanthropic weatherman Phil Connors heads to Punxsutawney, Pa., 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, on Amazon Prime, Google Play, iTunes, Vudu, YouTube

The Adventures of Priscilla, Queen of the Desert (1994)

Sequined dresses and lacquered nails can disguise a lot, but not the heart and generosity at the center of writer-director Stephan Elliott's LGBTQ fantasia about a pair of young drag queens (Hugo Weaving and Guy Pearce) and an aging trans woman (Terence Stamp) who travel in a silver bus into Australia's outback to vamp, lip-sync and fiercely perform for the glam-uninitiated. Best of all is Stamp, whose delicate, emotional turn anchors the giddy film.

Peak LOL moment: The trio's deliciously campy rendition of Gloria Gaynor's “I Will Survive” staged in the desert for an audience of Aborigines.

Watch it: The Adventures of Priscilla, Queen of the Desert, on Amazon Prime, Google Play, iTunes, Vudu, YouTube

Clueless (1995)

A consumerist, mall-rat coming-of-age story as filtered through Jane Austen's Emma. 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 Alicia Silverstone's haute couture outfits. It zips along like an expensive sports car. As the seemingly ditzy heroine Cher, Silverstone gives a tour de force performance with unexpected layers of innocence, altruism and humanity beneath all the bubbles.

Peak LOL moment: Cher's class presentation about Haitian refugees which she compares to the time she threw her father a birthday party and no one RSVP'd.

Watch it: Clueless, on Amazon Prime, Google Play, HBO Max, iTunes, Vudu, YouTube

Friday (1995)

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 is 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: Frankly, 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, on Amazon Prime, Google Play, iTunes, Vudu, YouTube

Austin Powers: International Man of Mystery (1997)

Mike Myers was one of the standouts during his tenure on Saturday Night Live, 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 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!” It's hard to choose which of those two brilliantly crazy performances is more inspired and blissfully strange. Yeah, baby, yeahhhh!

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, on Amazon Prime, Google Play, HBO Max, iTunes, Netflix, Vudu, YouTube

The Big Lebowski (1998)

"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, aka The Dude … or El Duderino if you're not into the whole brevity thing. Jeff Bridges is dazed-and-confused perfection as this caper's aging hippie hero, dividing 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, on Amazon Prime, Google Play, iTunes, Netflix, Vudu, YouTube

Anchorman: The Legend of Ron Burgundy (2004)

Will Ferrell's career is more or less composed of playing a menagerie of clueless blowhards who are funny because they're not aware that they're clueless or blowhards. Seventies San Diego anchorman Ron Burgundy is the pinnacle of that archetype. He's like Ted Baxter crossed with Burt Reynolds and someone who thinks he's Hugh Hefner. The Me Decade setting lends itself to fashion sight gags, Neanderthal chauvinism and the sort of unenlightened quips that feel ad-libbed under the cover of being self-aware. 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’ rumble sequence.

Watch it: Anchorman: The Legend of Ron Burgundy, on Amazon Prime, Google Play, iTunes, Vudu, YouTube

Bridesmaids (2011)

Kristin Wiig heads up a cast of comic actresses as on their game as the ‘27 Yankees in this comedy about 21st-century sisterhood and its discontents. Wiig plays Annie, a single woman in her mid-30s who dies a little inside when her best friend (Maya Rudolph) gets engaged and starts to plan her big day. Full of sly satire and broad slapstick, the film hums along thanks to the chemistry between Wiig and Rudolph (not to mention costars Rose Byrne, Wendi McLendon-Covey, Ellie Kemper and Melissa McCarthy in her breakout role). Bridesmaids is pure laughing gas. It's what happens when bad taste meets good humor on the way to the altar.

Peak LOL moment: Let's just say never go wedding-dress shopping while suffering from food poisoning.

Watch it: Bridesmaids, on Amazon Prime, iTunes, Peacock, Vudu, YouTube