Throughout the selection process to find the funniest comedies, we kept echoing the same mantra: “Is this movie really that good?” The answer was consistent: shouts of “it’s hilarious!” were parried just as assuredly by “it sucks!” Comedy, we quickly discovered, is just as diverse and polarizing as drama. Really the two aren’t so different. The best of both make us think and elicit a strong emotional response; the worst of both make us reach for our Hollywood-producer-window-breakin’-brick. Both are near and dear to our hearts because we identify with them. After an irrational amount of hemming and hawing we came up with our fifty favorite funny movies, ranging from slapstick to black-as-they-come to downright strange. Regardless of their tone, each of our picks bring just the right amount of levity to keep us smiling.
Now, without further ado, grab some popcorn, queue up the comedy flick, sit back, and dim the lights. The show’s about to start.
Methodology: like our books piece, the selections for our Definitive Men’s Movie Collection represent our favorites, “considered in the light of how much they changed our lives, and might change yours.” If it makes you feel any better that your favorite flick didn’t make the cut, consider that one of our auditors, in a moment of weakness, tried to get Nick Cage’s Ghostrider on the docket. Taste is subjective, so take this for what it’s worth.
When two rival con-men, played by Steve Martin and Michael Caine, realize that the French riviera isn’t big enough for the both of them, they engage in a friendly competition: the first one to con an American soap heiress out of $50,000 gets to stay.
Amazon DVDPlanes, Trains and Automobiles
Travel companions can suck. How much? Steve Martin finds out with the help of a clueless boob played beautifully by John Candy.
Amazon DVD / Amazon Download / Netflix / iTunesAustin Powers: International Man of Mystery
Mike Meyers is at his best in the genius foil of 007. Stupid humor? Absolutely. But it hits the mark. This sort of thing is our bag, baby.
Amazon DVD / Amazon Download / iTunesThe Big Lebowski
A movie that is, in hindsight, about a whole lot of nothing…and bowling. There are a lot of ins, outs, what-have-yous, though. See what the obsessive quoting is all about.
Amazon DVD / Amazon Download / iTunesSwingers
Vince Vaughn teaches Jon Favreau (both in significantly skinnier forms) how to be cool as they peruse the LA lounge scene. So Money.
Amazon DVD / Amazon Download / iTunesThe Graduate
A classic coming of age film featuring Ann Bancroft, Katherine Ross and an Alfa Spider. Win, Win and Win.
Amazon DVD / Amazon Download / iTunesTrading Places
Eddie Murphy is a beggar and Dan Akroid is a slightly snobbish banker; they swap roles at the whim of two stodgy old dudes. Both Akroid and Murphy at their absolute best. For bonus points, watch it around Christmas time.
Amazon DVD / Amazon Download / Netflix / iTunesCaddyshack
The goings-on at an exclusive Country Club in the 80’s. The main plot centers around Chevy Chase as Danny, a caddy trying to save up for college. The movie also focuses on the club’s eccentric members, pesky rodents, and general Chase-, Murray- and Dangerfield-induced antics.
Amazon DVD / Amazon Download / iTunesDeath at a Funeral
The funeral of an eccentric, dysfunctional family’s patriarch spirals out of control as his purported gay lover makes an appearance. Prepare yourself for quality British humor.
Amazon DVD / Amazon Download / Netflix / iTunesThe Hangover
Guys being guys.
Amazon DVD / Amazon Download/ iTunesNational Lampoon’s Animal House
Belushi, Bacon, Sutherland, that cute girl from Raiders of the Lost Ark; the “College” sweatshirt, Germans bombing Pearl Harbor, and food fights. If you haven’t seen it, do so immediately.
Amazon DVD / Amazon Download / iTunesHappy Gilmore
Before Adam Sandler did the actor equivalent of panhandling on a street corner by making Grown Ups (and Grown Ups 2), he played a hockey player-turned-golfer in this mid-90’s classic. The game of golf has never been the same…don’t act like you haven’t tried to drive the ball like him at the range.
Amazon DVD / Amazon Download / Netflix / iTunesAirplane!
“Joey, do you like movies about gladiators?”
Amazon DVD / Amazon Download / iTunesFerris Bueller’s Day Off
A fast-thinking student decides to take the day off. Hijinks ensue. We wish we had been this cool in high school.
Amazon DVD / Amazon Download / Netflix / iTunes This Is Spinal Tap
So big that it defined its own genre, this rockumentary about Spinal Tap, the world’s loudest band, is still one of the funniest movies ever made.
Amazon DVD / Amazon Download / iTunes
The infamous Dr. Frankenstein’s grandson returns to Transylvania as the sole heir to his family estate, where he becomes obsessed with reviving the dead. A black and white spoof-style send up of the original Mary Shelley story; Gene Wilder helms a monster cast in a genius masterpiece.
Amazon DVDBlazing Saddles
In a dastardly plot to demolish the sleepy Wild West town of Rock Ridge in order to build a profitable railway, a new sheriff is installed in the hopes that he, a black man (!), will offend residents enough to drive them away. Classic, madcap, star-studded satire.
Amazon DVD / Amazon Download / iTunesGhostbusters
When Gozer the Gozerian tries to stage an unholy comeback via possessed persons, a crew of NYC-based parapsychologists are forced to battle evil itself (and a huge marshmallow man), all while covered in funky ectoplasm and spouting wit at every turn.
Amazon DVD / Amazon Download / Netflix / iTunesThe Blues Brothers
The Blues Brothers are on a mission from God to save the orphanage that saved them years before. To raise funds, they’ll have to get the band back together while evading capture from an increasing hoard of pissed-off people left in their wake. With more cameos than you can shake a tambourine at, this film is rife with quotable lines, timeless performances and incredible music.
Amazon DVD / Amazon Download / iTunesDuck Soup
In perhaps the most original, zany and classic comedy ever made, The Marx Brothers — fresh off the vaudeville circuit — are at their finest. Rufus T. Firefly (Groucho) steps in as leader of Freedonia, a bankrupt country, to lead them to financial stability…though perhaps he wasn’t the best choice.
Amazon DVD / Amazon Download / Netflix / iTunesArmy of Darkness
The third installment in the Evil Dead trilogy, Army of Darkness is over the top cranked up to 11. Bruce Campbell is truly at his finest by Raimi’s side. The name’s Ash. Housewares.
Amazon DVD / Amazon Download / iTunesDazed and Confused
All right, all right, all right…watch it, if only to see why everyone loves Matthew McConaughey.
Amazon DVD / Amazon Download / iTunesFletch
A quick-witted L.A. journalist and die hard Lakers fan snoops around a little too much when tapped for a favor, and calamity ensues, in typical mid-80s fashion. Chevy Chase in arguably one of his best roles.
Amazon DVD / Amazon Download / iTunesBeverly Hills Cop
The movie that taught every man how to lose a tail — the old banana in the tailpipe trick.
Amazon DVD / Amazon Download / iTunesAnchorman: The Legend of Ron Burgundy
Outrageous. Completely over the top. And yet, it set the bar for all comedies that came out in the past decade. The mustache never looked so awesome, and the 1970s never looked so funny. Prepare yourself for Anchorman 2, coming out in December.
Amazon DVD / Amazon Download / iTunes
A nearly prepubescent version of Val Kilmer is an American pop star who gets involved with the French resistance during WWII. The physical comedy and sight gags rise/fall to new levels during a rather stiff ballet scene.
Amazon DVD / Amazon Download / iTunesThe Pink Panther Strikes Again
The debonair and sophisticated Inspector Clouseau foils his new nemesis, former inspector Dreyfuss, who has been driven to criminal insanity by Clouseau. Using disguise technology slightly shy of Mission Impossible-level, Clouseau works his accidental magic. The highlight of the movie takes place in a gut-busting hand-to-hand combat session between Clouseau and his trusty assistant, Cato. Judo chop.
Amazon DVDMidnight Run
Robert De Niro’s role as an efficient and hard-edged bounty hunter is priceless as he pursues an embezzler, played by the dry Charles Grodin, whom the mob is trying to eradicate. With odd-couple-like antics they make their way from NY to LA. Watching FBI Agent Alonso Mosley get pissed off is especially entertaining.
Amazon DVD / Amazon Download / iTunesShaun of the Dead
Shaun and his equally under-achieving buddy, Ed, step out of their morass of an existence to combat zombies attempting to overtake the world. Wading their way through the undead, as well as family and relational drama, the daring duo wreak havoc and humor throughout and make the most of ’80s LPs and garden tools.
Amazon DVD / Amazon Download / iTunesThe Jerk
A dim-witted white man raised by a black family leaves his home and makes his way in the world, falls in love, and becomes a millionaire via the positively magnetic Opti-Grab invention. Never has a paddle ball been so desirable.
Amazon DVD / Amazon Download / iTunes
Not only one of the best comedies of all time, but one of the best movies of all time. Watch in awe as the brilliant Peter Sellers flawlessly portrays Group Capt. Lionel Mandrake, President Merkin Muffley, and the unforgettable Dr. Strangelove.
Amazon DVD / Amazon Download / iTunesOld School
Because when was the last time you went streaking without yelling, “We’re going up the quad and to the gymnasium!” or invited Snoop Dogg to your party without saying, “You can bring your green hat!” Exactly.
Amazon DVD / Amazon Download / iTunesWho Framed Roger Rabbit
Not the first movie to combine cartoons with live actors, but still the best by far. When Roger Rabbit is framed for the murder of Marvin Acme, it’s up to Eddie Valiant, a cartoon-hating detective, to save him.
Amazon DVD / Amazon Download / Netflix / iTunesMonty Python and the Holy Grail
Many of Monty Python’s movies could have made this list, though we picked the most quotable. Watch as several incredibly silly knights quest for the Holy Grail.
Amazon DVD / Amazon Download / iTunesA Night at the Opera
America’s greatest family comedy act, the Marx brothers, star in this film about two star-crossed, Opera-singing lovers. Classic. As a side note, did you know that Groucho Marx once won third place in a Groucho Marx look-alike contest?
Amazon DVD / Amazon Download / iTunesIn Bruges
This dark comedy about the aftermath of a botched assassination attempt takes place in fuckin’ Bruges. It has the distinction of being the only Colin Farrell movie that also stars a little person.
Amazon DVD / Amazon Download / iTunes / iTunesBorat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan
Jagshemash! With Da Ali G Show, Sacha Baron Cohen ushered in a new wave of comedy, one in which his (often unwilling) audience played the actors. This film, about faux-Kazakh documentarian Borat’s quest to find Pamela Anderson, mocks many of America’s idiosyncrasies and stereotypes. Warning: you will cringe.
Amazon DVD / Amazon Download / iTunesFriday
Turns out Ice Cube can do more than rap. Watch as he (and a young Chris Tucker) try to raise $200 — but mostly just smoke a lot of weed.
Amazon DVD / Amazon Download / iTunesWet Hot American Summer
There are two types of people in the world: those who went to summer camp, and those that didn’t. If you fall into the first category, you’ll enjoy this film. If not, you’ll at least have fun trying to pick out young Paul Rudd, Michael Ian Black, Bradley Cooper, Elizabeth Banks and Amy Poehler.
Amazon DVD / Amazon Download / iTunesNational Lampoon’s Vacation
The Griswolds’s epic road trip to Wally World rolls up all the epic fails of road trips. Watch it with your loved ones and feel slightly better about your relatively innocuous miseries.
Amazon DVD / Amazon Download / iTunes Stripes
When two friends decide the solution to all their problems is to enlist in the Army, insanity ensues. In the course of their follies, they completely re-vamp Army Basic Training and subsequently save the world.
Amazon DVD / Amazon Download / iTunes Slapshot
I went to a fight movie and a hockey game broke out. Paul Newman plays an aging coach/player trying to save his team and his marriage from folding. Slapshot showcases everything hockey fans love about the game, along with a comeback underdog story wrapped in raunch and laughs and enough innuendo to engage a thinking man.
Amazon DVD / Amazon Download / iTunesWedding Crashers
Two buddies crash weddings (and funerals, the dogs), hoping to score babes. Business is good until they take on the wedding of weddings and one of the buddies falls for Claire Cleary. Look for a primo cameo from Will Ferrell in one of his scumbaggiest roles.
Amazon DVD / Amazon Download / iTunes Tommy Boy
As if we’re going to make a funniest movies of all time list without including something by Chris Farley. In this classic, the lovable big man plays Tommy Callahan Junior, the dimwitted heir to a massive auto parts factory. When Tommy’s father, Big Tom, dies, it’s up to Tommy and Richard, a company executive, to keep the factory from going under.
Amazon DVD / Amazon Download / Netflix / iTunes The 40-Year-Old-Virgin
Judd Apatow (who was once Adam Sandler’s roommate, by the way) is responsible for many of the past decade’s greatest comedies, and this is no exception. The formula is simple: Andy, a forty-year-old employee at Best Buy, has never had sex, so his buddies try to get him laid. Crazy fact: Shelley Malil, who plays Andy’s hilarious Indian friend, is currently in prison for stabbing his girlfriend 20 times. Woah. Still damn funny in the movie, though.
Amazon DVD / Amazon Download / iTunes Bananas
A neurotic, effete New Yorker named Fielding Mellish tries to impress a girl by becoming involved with a revolution in a tiny Latin American nation called San Marcos. He ends up joining the revolutionaries and unwittingly becoming their leader. Howard Cosell provides play-by-play, twice.
Amazon DVD / Amazon Download / iTunesDumb and Dumber
This is a classic buddy comedy in which the wonderfully named morons Lloyd Christmas and Harry Dunne head halfway across the country to return a beautiful woman’s briefcase, not realizing that it contains ransom money. Kidnappers and a trucker named Sea Bass mean them harm. Co-starring Jim Carrey’s haircut and a chipped tooth.
Amazon DVD / Amazon Download / iTunesPCU
One of the greatest college movies ever made follows a naive pre-frosh visiting the fictional Port Chester University (based on Wesleyan University). While there, he pisses off most of the student body, gets involved with warring houses (“The Pit” and “The Order of the Balls and Shaft”), and tosses beef on some protestors. Jeremy Piven at his finest.
Amazon DVDOffice Space
Ever spent an extended amount of time in an uncaring corporate hellhole? This one’s for you. It won’t make up for years of soul-sucking toil, but it’s pretty darn funny.
Amazon DVD / Amazon Download / iTunesGrosse Pointe Blank
Professional hitman Martin Blank (John Cusack) reluctantly returns home to Grosse Pointe, Michigan, at the behest of his shrink for his 10-year high school reunion, where he rekindles the only romance that ever mattered to him, seeks to complete his latest contract and avoids his archrival Grocer (Dan Akroyd) the only way he knows how.
Amazon DVD / iTunes