The 50 Funniest Movies of All Time

30. Planes, Trains & Automobiles

Written, directed and produced by John Hughes, this 1987 classic paired two timeless comics at the top of their game, Steve Martin and John Candy. Set at Thanksgiving, this movie is an excellent ramp-up to the holiday season, but also embodies the vintage “road trip” genre we enjoy so much.

29. The 40-Year-Old Virgin

The film that propelled Steve Carell to stardom (and perhaps brought about the eventual downfall of The Office); the 40-Year-Old Virgin is a buddy comedy that was critically acclaimed and financially successful.  Much of the film was improvised, which, as we have seen, can be a vital ingredient to making a great comedy.

28. Wedding Crashers

In 2003 Vince Vaughn knocked it out of the park with Luke Wilson in Old School, and here he caught lighting in a bottle again, but this time with Luke’s brother Owen. They brought their pal Will Ferrell in for the obligatory cameo, too. “Ma! The meatloaf! We want it!!” This film brought Isla Fisher and Bradley Cooper to the party, and reminded us of how hot Jane Seymour is. Easily the best use of the now-overused “motorboat” term in pop culture history. The joy on Jeremy’s (Vince Vaughn) face when he asks John what happened upstairs is unmistakable.

27. The Jerk

Steve Martin’s epic tale of a man who’s just plain dumb. A fool and his money are lucky enough to get together in the first place, and this is the feature length adaptation of this axiom. The closest thing the big screen saw to Martin’s 1970s stand up comedy persona.

26. Dumb and Dumber  

Will Ferrell has his Anchorman, Steve Martin has his The Jerk and Chevy Chase has his Vacation. Jim Carrey’s masterpiece has to be Dumb and Dumber. The memories I associate with this film are my all time favorites. My friends and I saw this film at least 7 times in the theater, and the 7th time was by far the best. Knowing all the beats and jokes as we watched a newbie experience it for the first time- his eyes lit up with every “Aspin” and every snowball to the face. It was like a child on Lloyd Christmas morning.

25. Spaceballs

Starring Bill Pullman, John Candy, Rick Moranis, Daphne Zuniga, and Mel Brooks as both President Scroob and Yogurt, Spaceballs is a slapstick parody of science fiction films such as Star Trek, Alien, Planet of the Apes, and of course Star Wars.  While initially receiving mixed reviews it has since become one of Mel Brooks’ most popular films thanks to its cult status.

24. The Blues Brothers

Released in 1980 and directed by John Landis, The Blues Brothers is the second-highest grossing film based on a Saturday Night Live skit. The brothers were on a mission from God to clean up their act as they try to save the orphanage that they called home in their youth. This franchise has grown into much more over the years, including concerts, musicals, video games, bars, and restaurants.

23. The Big Lebowski

The Coen Brothers’ comedic masterpiece, The Big Lebowski is a surrealistic movie populated by oddball characters, creating a hysterical, unique movie. The Dude, Walter and Donny bowl and bumble their way through a kidnapping investigation. Jeff Bridges’ most beloved character.

22. Ace Ventura: Pet Detective

Jim Carrey was just “the white guy” on In Living Color before this ridiculously premised film debut. To an 18 year old high school senior the humor in this film was a dream come true- the man talked out of his ass for crying out loud. After this release Jim Carrey became a mega-comedic star and we were blessed with such gems as Dumb and Dumber, The Mask and even a second Ace Ventura, although its the first Ace that hits my funny bone and always reminds me to put the ‘laces out’.

21. The Naked Gun: From the Files of Police Squad

The first film of a series based on the short lived show, The Naked Gun is a slapstick comedy that was both a critical and commercial success.  Starring Leslie Nielson and Priscilla Presley, it brought bumbling detective Frank Drebin to the big screen where he belongs.

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