9. Happy Gilmore Some people will consider it sacrilige to name Happy Gilmore the best golf comedy of all time. Those people need to face reality. On the whole, Happy Gilmore is funnier, tells a better story, and has more heart than Caddyshack. Ask yourself these questions. Who carries his movie better, Adam Sandler as Happy Gilmore, or Michael O'Keefe as Danny Noonan? (A: Sandler. This was Adam Sandler's second film, and still his best.) Take Rodney Dangerfield out of Caddyshack and what are you left with? (A: Sub-par Bill Murray and Chevy Chase schtick.) Take Carl Weathers out of Happy Gilmore and what are you left with? (A: Still a great, classic comedy.)
8. Office Space This movie is very quotable, particularly if you work in an office environment, wherein people are required by law to quote it whenever possible. No film has captured the absurdity of office life the way Office Space did. Mike Judge really came up with a gem here.
7. Fletch This is Chevy Chase schtick at its best. A perfect match of material to actor. There has been talk of rebooting this franchise for years, but it's hard to imagine someone other than Chase playing Fletch.
6. South Park: Bigger, Longer and Uncut This animated feature is an assault on the senses. It's almost overwhelming the first time through. But damn, it's really rude, and really funny. The songs are great, the gags work, the South Park formula translated to the big screen in a surprisingly effective way.
5. Tommy Boy Chris Farley and David Spade made such a great team in this movie and showed so much promise for the future, it's one of the reasons Farley's early death was tragic; it seemed like he had so much potential to make great comedies, particularly when paired with Spade. Tommy Boy is the quintessential road trip movie (Vacation is a close second). Really good comedy combined with a good story and a touch of heart.
4. Young Frankenstein A classic Mel Brooks film. Gene Wilder and Brooks put together this masterpiece of comedy in the same year as Blazing Saddles. Talk about being at the top of your game! Everybody is great in this film, Wilder, Teri Garr, Peter Boyle, Marty Feldman, Cloris Leachman, Madeline Kahn, and Kenneth Mars. Sedagive!?!
3. Kingpin Bill Murray's signature role is probably Phil Connors in Groundhog Day, but for my money, Ernie McCracken in Kingpin is the best and funniest work Murray has ever done on film. Similarly, the Farrelly brothers are most well-known for There's Something About Mary, but Kingpin is clearly the superior comedy. Woody Harrelson also delivers one of the best performances of his career.
2. Blazing Saddles Here's a movie that could not get made today. Watch the clip to see what I mean. There are so many great things about this picture: Gene Wilder's drunken sharpshooter, Mel Brooks's writing and direction, Madeline Kahn's temptress, Alex Karras as Mongo, and Cleavon Little as the star of the show.
1. Airplane! There is not a more quotable comedy than Airplane!. From "looks like I picked the wrong week to quit smoking/drinking/amphetemines", and "don't call me shirley", to "Joey, do you like movies about gladiators?" This is the king of rewatchable comedy, the ruler of one-liners, the prince of parody.
Honorable mention: Austin Powers: International Man of Mystery Very clever spoof of spy and action movies from Mike Myers. Lots of classic bits in this picture.
Honorable mention: Monty Python and the Holy Grail Monty Python's piece de resistance.
Honorable mention: Stripes Bill Murray has been in a lot of classic comedies, this is one of my personal favorites.
Honorable mention: Ace Ventura: Pet Detective Over time, this movie hasn't held up quite as well as the others, but I laughed my ass off the first time I saw it.