Compiling a list of the funniest movies of all time is a bit like coming up with a list of the best pizza toppings of all time. Humor is so subjective, and a joke that would have one person rolling on the floor in a helpless fit of giggles might not even elicit so much as a smile from a different person. The same comparison could be made for pizza toppings. We all have vastly different tastes, so one person's mouthwatering delight might be another's vomit-inducing culinary nightmare. Pepperoni is the notable exception to this rule, of course. Everyone knows it is number one!
That said, it is always a fun exercise to write a list like this just to see what sort of friendly (or heated) debate it will cause. I fully expect readers of this article to rake me over the coals for the selections I've made, or omitted from this list. Bring on the debate!
20 - Planes, Trains & Automobiles
Two of the biggest heavyweights of comedy in the 80s were Steve Martin and John Candy, and the two make an awesome team in this 1987 Thanksgiving classic from director John Hughes. Neal Page (Steve Martin) wants nothing more than to get home to his family in Chicago, but when he is seated next to shower curtain ring salesman Del Griffith (Candy) his plans go right out the window. The friendly, but overbearing Griffith is the polar opposite of the buttoned-down, uptight Page and tension rises between the two as one disaster after another befalls them on his hilarious journey. Those aren't pillows!
19 - The Hangover
Though a pair of uninspired sequels has really watered down the franchise, this surprise hit had audiences howling with laughter when it hit theaters back in 2009. The film made Bradley Cooper, Ed Helms and Zach Galifianakis household names, and even showed that ex-boxer Mike Tyson had some comedic chops. The movie really didn't break new ground plot-wise, but the dialogue and the interaction between the members of "The Wolfpack" really set it apart from other similar buddy movies.
18 - The Party
Though a lot of people will probably argue that Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb was the funniest Peter Sellers movie in my opinion this underrated gem is the best comedic work of the late English funnyman. Sellers is at his bumbling best as Indian film star, Hrundi V. Bakshi who screws up royally on set and instead of getting fired is accidentally invited to an exclusive Hollywood party. As he makes his way through the posh affair chaos just seems to naturally follow in his wake, and every attempt to rectify things just make things worse.
17 - Animal House
College fraternity movies are a dime a dozen in Hollywood, and while once in a while a classic like Old School comes along to challenge for the throne this 1978 film by director John Landis remains the gold standard in this popular sub-genre. Dean Wormer tries his best to expel Otter (Tim Matheson), Bluto (John Belushi) and the rest of the trouble-making fraternity, Delta Tau Chi, but his efforts are consistently foiled by the toga-wearing gang.
16 - There's Something About Mary
This wasn't Cameron Diaz's first movie role, but it was surely the one that launched her to stardom. The blonde beauty becomes the object of affection for every man she encounters. Ben Stiller's character Ted has his work cut out for him as he not only tries to punch above his weight class to win the hand of the gorgeous Mary, but has to compete with four other rivals, including Brett Favre! Like other Farrelly brothers movies there is definitely some gross humor, but it hits all the right notes and will have you laughing and gagging all at the same time.
15 - Groundhog Day
While Steve Martin and John Candy were among the biggest comedy film stars of the 80s there can be little argument that Bill Murray was the undisputed king of laughs during that era. Though his star started to fade a bit in the 1990s, he saved one of his best performances for 1993 with the Harold Ramis-directed classic Groundhog Day. Murray is awesome as Phil the weatherman, who finds himself trapped in a time warp, living the same day over and over, after getting caught in a blizzard he didn't predict. Though the movie sounds like it would be (and admittedly is) repetitive, it never gets dull as everybody's favorite Ghostbuster somehow manages to keep things fresh despite going through the same routine day after day.
14 - The 40 Year Old Virgin
Though Steve Carell has since become a household name, starring in the American version of the hit sitcom The Office and a multitude of feature films over the last dozen years he really launched into the public eye with this 2005 laugh-fest. Carell plays Andy, a 40 year old action-figure-collecting, bicycle-riding nerd who has never "done the deed". When his buddies at work discover this fact they force him out on the dating scene to rectify this untenable situation. He goes on a series of bizarre dates, looking to stamp his V card, but in the end true romance wins out.
13 - Life of Brian
I'm sure that those across the pond are going to complain that this list is a bit too heavy on North American film content, but I am not just throwing them a bone by including this 1979 classic by Britain's funniest comedy troupe. John Cleese, Graham Chapman and the rest of the Monty Python gang poke not-so-gentle fun at Christianity and while the bible thumpers in the crowd will probably give it a resounding thumbs-down everyone else is in for a good laugh.
12 - Office Space
Much like the television show The Office this peek into cubicle culture will definitely ring true with a whole lot of people who've experienced the drudgery of 9-5 under the fluorescent lights. Ron Livingston gives a career performance as Peter Gibbons, a disenchanted employee at Initech who, after a hypnotherapy session gone awry removes his inhibitions, hatches a plan to get what's his from the company by setting up a software program to embezzle a fraction of a penny at a time.
The movie has become a cult classic and almost 20 years after its release remains relevant and quotable, and Gary Gole's character Bill Lumbergh has earned a place in cinematic history as one of the best movie "villains" of all time.
11 - Duck Soup
Yes, I realize that there were funny movies before the 1970s, and that this list is heavily skewed toward modern films, but our sense of humor tends to mirror our environment, and it is often hard to identify with the comedy of an era decades before we were born. However, there are some actors that manage to transcend that barrier and the legendary Groucho Marx is certainly chief among them.
Groucho, along with Harpo, Chico and Zeppo are at their goofy best in this 1933 classic set in the fictional country of Freedonia. Groucho's physical comedy is so good that you could probably turn the sound off and still find yourself cracking up.
10 - Dumb and Dumber
Though Something About Mary was a hilarious film, without a doubt the best of the Farrelly brothers' movies was 1994's Dumb and Dumber. Jim Carrey and Jeff Daniels make a superbly stupid team in this cross-country adventure of two intellectually challenged friends who inadvertently manage to foil a gang of criminals. Daniels, more known for dramatic roles, proves to be surprisingly funny as Harry Dunne, and Carrey, known for roles such as Ace Ventura and The Mask is arguably at his absolute laugh-inducing best as Lloyd Christmas.
9 - Anchorman: The Legend of Ron Burgundy
Will Ferrell's film career has had been a bit of a roller coaster ride, with a few peaks and probably a lot more valleys. However, he definitely found the right recipe, and created an iconic character in 2004 when he introduced the world to Ron Burgundy. In the role he was born to play Ferrell is utterly convincing as a mustache-sporting, Sex Panther cologne-wearing, misogynist 1970s television anchorman. Paul Rudd, David Koechner and Steve Carell are all fantastic in support, and Christina Applegate gives the performance of her career as Veronica Corningstone, an up-and-coming anchorwoman determined to turn the industry on its ear and the object of Ron's affection.
Often ridiculous, even downright goofy, Anchorman won't be for everyone, but if you are a fan of lowbrow humor it doesn't get much better than this.
8 - Annie Hall
While most of the films on this list received no critical acclaim at all, the same can't be say of Woody Allen's 1977 masterpiece. The semi-biographical Annie Hall cleaned up at the Oscar's the following year, earning awards for Best Actress (Diane Keaton), Woody Allen (Best Director) to go along with the big prizes of Best Screenplay and Best Picture, defeating a little film by the name of Star Wars along the way. Like most of Allen's films there is plenty of wit and definitely far more depth than your average comedy and the viewers get a peek into the souls of Keaton and Allen and their real life relationship.
7 - Some Like it Hot
While I'm not going as far back in the film annals as I did with Duck Soup, I am definitely well and truly out of the modern era of comedy with this 1959 selection. For once comedy legend is without his usual partner Walter Matthau, instead teaming up with Tony Curtis in this groundbreaking film about two musicians who have to dress in drag to save their own skins after witnessing a mob hit. Gender barriers start to get confusing as Joe/Josephine (Tony Curtis) starts to woo Sugar Kane Kowalcyk (Marilyn Monroe) and Jerry/Daphne (Jack Lemmon) becomes the object of affection of another man.
6 - Caddyshack
Bill Murray makes another appearance on the list, though this time in a supporting role, in 1980's Caddyshack. Murray is hardly alone in carrying the comedic load in every golfer's favorite movie. Chevy Chase, Rodney Dangerfield and Ted Knight keep the laughs coming. There was actually an ill-conceived sequel released in 1988, but featured none of the big stars of the original and was a flop.
5 - Blazing Saddles
No list of the funniest movies of all time would be complete without at least one entry from Mel Brooks. Though my personal favorite Mel Brooks movie is Spaceballs, Blazing Saddles is a close second, and is, I think, universally acknowledged as his funniest movie. Anyone watching it should know that the film is about as far from politically correct as it gets, and definitely contains some situations that will definitely shock first-time viewers. Brooks has been known to push the boundaries throughout his career and has acknowledged that the film probably wouldn't get made today.
4 - Airplane!
Perhaps the most quotable comedy of all time, Airplane! was a parody of the slew of airline disaster movies that hit screens in the 1970s. Comedy legends Lloyd Bridges and Leslie Nielsen are at their funniest, and the rest of the cast - even Kareem Abdul-Jabbar - keep the laughs coming nonstop in this very literal comedy in the spirit of Police Squad!, The Naked Gun and Hot Shots.
3 - The Big Lebowski
If I'd included this film on a list of funniest movies shortly after its 1998 release people would have scoffed in derision. However, over the last couple of decades this Coen brothers' masterpiece has gained an ever-growing cult following of devoted fans of The Dude. With a convoluted plot featuring a lot of "ins and outs and what-have-yous" The Big Lebowski is a film that can only be appreciated by multiple viewings. The dialogue between The Dude (Jeff Bridges), Walter (John Goodman) and Donny (Steve Buscemi) is gut-busting, particularly in the bowling alley scenes. John Turturro nearly steals the film in his turn as Jesus Quintana, a rival bowler and a known pederast. If you haven't seen the film, or only watched it once and dismissed, do yourself a favor and watch it again (and again).
2 - This is Spinal Tap
Anyone who is a fan of parodies or mockumentaries has almost certainly already seen this film, but if you've somehow missed it, then stop reading this article and rectify the situation immediately. Rob Reiner directs and stars in the film as a documentary filmmaker who chronicles the life and times of the British heavy metal group, Spinal Tap. The mockumentary is so well done that a casual viewer tuning in might be fooled into thinking they were watching a genuine story of a real group.
1 - Monty Python and the Holy Grail
It should come as little surprise to anyone that this Monty Python masterpiece heads up the list of the funniest movies ever made. As good as Life of Brian was, this film is not only the pinnacle of British comedies, but of all comedy films in general. The film is very loosely based on the story of King Arthur and his Knights of the Round Table, in which Arthur and his knights set out on a quest to for the grail and are beset by increasingly silly obstacles along the way, including an extremely rude Frenchman, a black knight that refuses to give up, a carnivorous rabbit and a powerful wizard that some call Tim.
Well, there you have it - my picks for the funniest movies ever made. Disagree with my selections? I look forward to your comments and criticisms. Thanks for reading.