Top 50 Funniest Films Counted Down
50 - Wedding Crashers - Vince Vaughn and Owen Wilson team up to deliver the laughs about two bachelors who charge up their sex lives by crashing weddings on weekends. Christopher Walken is also great in a supporting role, delivering one of his signature monologues.
49 - Van Wilder - Ryan Reynolds shows his penchant for comedic timing in this college campus comedy that pays some homage to the ultimate college fraternity flick Animal House. The film was also the coming out party for Kal Penn, who went on to make a name for himself in Harold and Kumar Go To Whitecastle.
48 - Austin Powers: International Man of Mystery - Canadian funnyman Mike Myers stars as a British secret agent in this spoof of the James Bond movies. He works double time, also filling the role of Dr. Evil, Austin Powers' nemesis. Elizabeth Hurley plays Austin's love interest, the indescribably hot Vanessa Kensington. Sorry, no Mini Me in this one.
47 - Dumb & Dumber - Jim Carrey and Lloyd Bridges star as Lloyd Christmas and Harry Dunne, two unbelievable morons who somehow manage to outwit a gang of criminals.
46 - Christmas Vacation - Chevy Chase is back as Clark Griswold, the well-meaning, but bumbling family man who wants nothing more than to give his family the best Christmas ever. Unfortunately, things just don't work out.
45 - Slapshot - This one is for all the Canadians out there. Slapshot is the best hockey movie ever made, hands down, and Paul Newman is surprisingly good in the role of player coach Reg Dunlop. However, as any fan of the movie will tell you it is the Hanson brothers who really steal the show.
44 - American Pie - A bunch of high school seniors make a pact to lose their virginity. By the end of the film it is mission accomplished, but not without some hilarious failures along the way. Seann William Scott turns in one of the iconic performances of the 90s with his turn as Steve Stifler.
43 - Monty Python's: Life of Brian - If this were a list of the top 10 British comedy movies of all time this legendary troupe would be all over it. Graham Chapman stars as Brian, who is mistaken for the Messiah. Michael Palin, Eric Idle, John Cleese and the rest of the crew are in top form in this religious spoof.
42 - Meet the Parents - Ben Stiller and Robert De Niro are at odds when Stiller's character, male nurse Gaylord Focker, proposes marriage to Jack Byrnes' (Robert De Niro) daughter. Focker makes a bad first impression and then compounds it by making a 2nd, 3rd and 4th bad impression. De Niro is surprisingly hilarious, and Stiller is at his goofy best.
41 - The Princess Bride - Cary Elwes, Robin Wright Penn, Mandy Patinkin and Andre the Giant all star in this very clever fable/ romantic comedy about true love. Plenty of great quotes, lots of action, and a hilarious cameo from Billy Crystal make this one of the best comedy movies of all time.
40 - When Harry Met Sally - This time Billy Crystal is in the lead role, starring alongside cute as a button Meg Ryan in this 80s romantic comedy about two longtime friends who resist the urge to take their relationship to a sexual level for fear it might ruin their friendship.
39 - Napoleon Dynamite - Not only one of the funniest movies of all time, but certainly one of the weirdest, Jon Heder stars as Napoleon, who tries to help his friend Pedro win the class presidency while dealing with all sorts of weirdness at home with his brother Kip and his Uncle Rico.
38 - The Pink Panther - Peter Sellers is at the top of his game as the iconic Inspector Jacques Clouseau in this classic comedy film about a jewel heist. Sorry Cato fans, no martial arts battle in this one.
37 - Ghostbusters - SNL alum Bill Murray and Dan Akroyd team up to fight a paranormal menace that is threatening New York. Along the way they fight a 300 foot Stay Puft marshmallow man, demon dogs, a hotdog gobbling ghoul named Slimer, and a god who wants to gain entry into the world. Sigourney Weaver, Harold Ramis and SCTV star Rick Moranis are fantastic in support.
36 - Father of the Bride - Not the 1991 Steve Martin version, but the original comedy classic starring film legends Spencer Tracy and Elizabeth Taylor about a man who must deal with his daughter's impending wedding.
35 - The Naked Gun: From the Files of Police Squad - Another Canadian comedian tickles our funny bones in this cop movie spoof. Leslie Nielsen of Airplane! fame stars as Lt. Frank Drebin, a bumbling cop who must somehow foil an assassination plot against Queen Elizabeth II. OJ Simpson, Ricardo Montalban and Priscilla Presley co-star.
34 - Old School - Luke Wilson, Vince Vaughn and Will Ferrell star as three middle aged guys who relive their glory days by starting up a college frat house. Ferrell is especially funny as Frank the Tank, and Jeremy Piven who is so excellent as Ari Gold on Entourage plays their nemesis, Dean Pritchard. One of the best recent comedy movies to hit theaters.
33 - Young Frankenstein - Director Mel Brooks and comedian Gene Wilder team up to deliver one of the funniest horror movies ever made. Plenty of monster movie hijinx from this legendary comedic pair.
32 - Vacation - Though Christmas Vacation may get the sentimental vote for a higher spot on the list of the top 50 funniest movies of all time it is my contention that the original still stands above. In Vacation we are introduced to Clark Griswold and we can't help but laugh at his hapless efforts to get his family across the country to visit the theme park Wally World. Another film featuring some great cameos as both Christie Brinkley and John Candy get in on the action.
31 - Clerks - This little indie movie by director Kevin Smith about two convenience store clerks has gone on to become one of the biggest cult movie hits of all time. It is shot in black and white but that only adds to its charm. Smith himself appears as Silent Bob, sidekick to Jay (Jason Mewes). Though some might prefer films like Dogma, Mallrats or Zack and Miri Make a Porno I still think this highly original comedy is Smith's best work.
30 - The Incredibles - This could make a list of the top 10 animated films of all time, but director Brad Bird's and movie studio Pixar's Incredibles is also plenty funny as well. Craig T. Nelson, Holly Hunter, Samuel L. Jackson and Jason Lee all turn in top notch voice acting performances in this superhero movie parody.
29 - Ace Ventura: Pet Detective - Yes The Mask, The Cable Guy, Liar Liar, and the Truman Show were all good, but this over the top comedy about a private investigator with an unusual affinity for animals is still Jim Carrey's best performance to date. If you don't mind a little over the top acting definitely check it out.
28 - Caddyshack - Plenty of comedic clout in this golf movie. Bill Murray, Chevy Chase, Ted Knight, and Rodney Dangerfield all lend their humor and their talent to this classic 1980 film. Better than Tin Cup, The Legend of Bagger Vance, or even Happy Gilmore, Caddyshack is the best golf movie of all time.
27 - Kingpin - From golf to bowling, obviously leisure sports make for good comedic potential. Woody Harrelson stars as Roy Munson, a former pro bowler who lost his bowling hand and is now trying to live his dream vicariously through a young Quaker bowling prodigy (Randy Quaid). Bill Murray plays the bad guy this time around as Roy's nemesis Ernie McKracken. Plenty of laughs and gross humor in this Farrelly brothers' film.
26 - The Odd Couple - Jack Lemmon and Walter Matthau made a career of starring opposite one another, and this charming comedy about two men, polar opposites, trying to share a small apartment will have even the most dour person smiling throughout. An easy pick as one of the best comedy movies of all time.
25 - M*A*S*H - Before Alan Alda and the gang went on to huge success on the TV show, Donald Sutherland, and Elliott Gould were starring as swampmates Hawkeye Pierce and Trapper John McIntyre on the big screen. Classic goofy humor every bit as good as the TV show was. If you liked the show but haven't seen the movie definitely give it a watch.
24 - A Fish Called Wanda - Not an official Monty Python flick, but those goofy British geniuses certainly have their fingerprints on it. John Cleese and Michael Palin lend their peculiar brand of humor to this criminal caper. Jamie Lee Curtis and Kevin Kline also do a magnificent job.
23 - Swingers - The movie that made the careers of Vince Vaughn and Jon Favreau is another of the biggest cult comedy movies of all time. They were so money and they didn't even know it. Dialog driven with plenty of great quotes Swingers is one of those rare movies you can watch over and over again without getting tired of it.
22 - Harold and Maude - Like black comedy? Try this movie about Harold, a twenty year old guy who is fascinated by death and shows it by faking suicides and attending random funerals. He meets Maude, a 79 year old firecracker who teaches him about life. Despite the nearly 60 years between them Harold proposes marriage. Sorry, you'll have to watch the film to find out what her answer is.
21 - Moonstruck - Cher turns in an Oscar winning performance in this romantic comedy with a bit of a twist on the old love triangle plot. One of the best comedies of the 80s, and far and away Cher's best performance as an actress.
20 - Duck Soup - Here we are entering the top 20 funniest movies of all time, and it is only fitting that one of the greatest comedians of all time stars in the movie that marks the milestone. Groucho Marx, along with Harpo, Zeppo and Chico will make you howl in this 1933 classic comedy about war, love and most centrally money. If you haven't seen the Marx brothers in action before, definitely check out Duck Soup for a crash course in their comedic brilliance.
19 - American Graffiti - Though George Lucas will always be remembered first and foremost for the Star Wars movies, he did have his hand in another classic American movie. American Graffiti might not have a deep plot - most of the film is about a group of teenagers cruising around town - but it is one of those movies that everyone of that age or has ever been that age can identify with. The soundtrack is legendary, and the movie helped launch the careers of Hollywood heavyweights like Richard Dreyfuss, Ron Howard and Harrison Ford.
18 - Some Like It Hot - Blond bombshell Marilyn Monroe stars alongside Tony Curtis and Jack Lemmon in this uproariously funny comedy about a pair of guys who must dress in drag and join an all women band in order to avoid execution by the mob. Plenty of twists, turns and complications, and an endless supply of laughs.
17 - Tootsie - Dustin Hoffman gives one of the best performances of his career in Tootsie, where a struggling male actor dresses up as a woman in order to land a plum role on a soap opera. To make matters more complicated he proceeds to fall in love with one of the actresses on the show.
16 - Shrek - Mike Myers, Cameron Diaz, Eddie Murphy and John Lithgow all star is this breakthrough animated comedy about an ogre who must go on a quest to rescue a princess in a vain attempt to get some peace and quiet. If you haven't seen Shrek or its sequels then you must be living on a different planet. Come on back down to Earth and check it out.
15 - Animal House - The late great John Belushi stars as Bluto in what is arguably the greatest college movie ever made in any genre. Toga parties and food fights abound. If you like pranks, raunchy humor, and/or John Belushi's incredible comedy you'll love this movie.
14 - Fast Times at Ridgemont High - From the best college comedy film of all time to arguably the best high school comedy ever made. Sean Penn stars as stoner Jeff Spicoli in this classic 80s film about life in high school. Jennifer Jason Leigh and a young Judge Reinhold also star. Though some of the subject matter is certainly dark and depressing there is more than enough laughter to balance it out.
13 - There's Something About Mary - More like a love hexagon than a love triangle Something About Mary stars Cameron Diaz as the woman that every man wants. Ben Stiller, Matt Dillon and even Brett Favre count themselves among her many suitors, and the constant battle to get her attention keeps the laughs coming in this Farrelly brothers' comedy classic.
12 - The Party - Peter Sellers makes another appearance on the list of the top 50 funniest movies of all time this time starring as Hrundi V. Bakshi, an incredibly clumsy movie extra who inadvertently gets invited to a party instead of getting fired after causing chaos on the movie set. The chaos continues when he arrives at the party and it isn't long before he has the host wanting to kill him.
11 - This is Spinal Tap - Rob Reiner, best known for his directorial work, stars in this rockumentary about the world's loudest heavy metal band. A fantastic parody of the rock music scene with consistent laughs throughout. If you like spoofs then I guarantee you will love this film.
10 - Superbad - One of the best recent comedy movies has already gained entrance to the top 10 funniest films of all time. Michael Cera and Jonah Hill star as two buddies who go to great lengths to procure alcohol and get to a party where the women of their dreams are waiting for them. Seth Roger and Bill Hader also star, but it is the unknown Christopher Mintz-Plasse who really steals the show, as the 25 year old Hawaiian organ donor McLovin.
9 - Planes, Trains and Automobiles - The late Canadian comedian John Candy stars alongside SNL legend Steve Martin in this movie about two strangers trying to get home for the Thanksgiving holidays. Much like Lemmon's and Matthau's odd couple they mix like oil and water, and their contentious relationship provides constant laughs throughout the film.
8 - The Producers - Actor Gene Wilder and director Mel Brooks are at it again in this 1968 Oscar award winning film about two producers who try and execute a swindle by deliberately making a box office flop. The 2005 remake starring Nathan Lane and Matthew Broderick was surprisingly good, but still could not live up to the high standard set by the original.
7 - Annie Hall - Arguably Woody Allen's most famous screenplay, Annie Hall is a partially autobiographical look at Allen's life and his relationship with Diane Keaton, who also acts in the film, in 1970. Though Woody Allen's career is certainly not as bright as it once was one need only to watch this film to realize just how brilliant a writer he was in his heyday.
6 - Blazing Saddles - Arguably the best comedy film of the 1970s Mel Brooks' Blazing Saddles could easily make a list of the best western movies of all time. No surprise that Gene Wilder is involved again, and Slim Pickens and Cleavon Little also star. Blazing Saddles is undeniably funny, but there are many who may be offended by the racial epithets in the film. Be warned that this is not the politically correct comedy you've grown used to in this day and age.
5 - Brazil - Another weird one helps mark our entrance into the top 5 best comedy movies ever made. Terry Gilliam's Brazil is certainly funny, if you can manage to follow the convoluted plot. Try a long term rental, or see if you can find this one in the DVD bargain bin of the video store. You'll have to watch it three or four times before you get things sorted out.
4 - The Big Lebowski - Bowling, rug theft, nihilists and White Russians are all central to the plot in this hilarious case of mistaken identity. The Coen brothers followed up their Oscar winning Fargo with another brilliant film, and Jeff Bridges, John Goodman, Steve Buscemi and John Turturro all turn in masterful performances. Much like Brazil The Big Lebowski takes a few viewings to get everything sorted out, but once you do you'll truly appreciate the brilliance of this film.
3 - Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb - Before Mike Myers was working overtime as Austin Powers and Dr. Evil Peter Sellers was doing the same, playing three roles in this bizarre comedy that pokes a little fun at the Cold War that was brewing between the United States and the Soviet Union at the time film was released. One of the best comedies of all time, and perhaps Peter Sellers' greatest achievement as an actor.
2 - Airplane! - The ultimate spoof movie gets the runner-up prize on this list of the greatest comedy films ever made. Airplane! pokes fun at the sub-genre of airline disaster movies and Robert Hays, Leslie Nielsen, Robert Stack and the legendary Lloyd Bridges keep the puns and the one liners flying throughout the film. Even basketball star Kareem Abdul-Jabbar gets into the act. Perhaps no movie before or since is more quotable. If you love parodies and you've somehow missed this one be sure you rectify that immediately.
1 - Monty Python and the Holy Grail - It's no surprise that the Monty Python gang would top the list of the top 50 best comedy movies of all time. Graham Chapman stars in the lead role in this hilarious take on the legend of King Arthur and his Knights of the Round Table. Colorful characters abound, from Arthur himself to the Black Knight, the rude Frenchman, Brave Sir Robin, and the Knights Who Say Nii. If you really want a laughfest rent Holy Grail, Life of Brian and Meaning of Life and watch them all back to back. I promise your stomach will be aching the next day from all the laughing you did the night before.
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