1. Orange County
Here's a movie that works better than it should. There's the pretty familiar inverted fish out of water storyline here, but there's such a good collection of supporting characters with Jack Black, John Lithgow, Catherine O'Hara, Schuyler Fisk, and a lot other small performances that crowd the movie with a variety of qualities and styles. It works well is what I'm trying to say.
2. My Big Fat Greek Wedding
The biggest sleeper hit of all time. In the vein of Meet the Parents, it reminded people how families can be funny. It's weird how, with all the good performances from B-list (or lower) actors, it didn't help anyone (especially Nia Vardalos) into the A-list.
3. Punch-Drunk Love
Sure, this might be more of a drama. It is still pretty funny and Adam Sandler going extremely against character is a delight. I recommend it, but not to anyone expecting Happy Gilmore.
4. About a Boy
A pithy little British comedy. It features Hugh Grant in his asshole character rather than his [as Family Guy calls it] charmingly befuddled RomCom persona. Like a lot of British comedy, there a darker edge to it, but still greatly enjoyable.
5. Death to Smoochy
Zany dark comedy with a great cast. It examines the zany underworld of kid's shows. An excellent cast including Edward Norton, Robin Williams, Catherine Keener, and Danny DeVito. Although it isn't for everyone.
6. Mr. Deeds
Pretty standard fare for an Adam Sandler comedy. Not one of his best. Still better than a lot of things out there. A traditional fish out of water story (yeah, I know I'm using that phrase a lot), Adam Sandler plays a naive guy, Winona Rider tries not to steal anything on set, Peter Gallagher playing the asshole he plays so well, and a bunch of Happy Madison regulars doing their thing.
7. National Lampoon's Van Wilder
A 21st century attempt at Animal House. This is the blessing and the curse of the movie. National Lampoon got people noticing it, but the inevitable comparison hurt it. Ryan Reynolds plays the titular character (otherwise known as the Ryan Reynolds character). It also has Tara Reid when she was still hot and Kal Penn before he stopped getting cast as racist Indian stereotypes.
HONORABLE MENTION
Jackass: The Movie
I'm eternally on the fence about these movies. I respect physical comedy as being legitimate comedy, but I really hate their brand of it. Still, it is able to make me laugh despite myself.
Scooby-Doo
Retro and stupid. A children's movie with some humor for adults. A stronger cast than it probably deserved all pulled from the late 90s teen comedy circuit.
Two Weeks Notice
It's your prototypical Grant-ian Romantic Comedy, but I give it props simply for how enjoyable Sandra Bullock and Hugh Grant are together, on or off camera.
The New Guy
I know people who swear by it. It's hurt in my book because I don't like Eddie Griffin. What we have here is a very standard movie. Nothing of note to hurt or help it's case. Considering how many movies fail to achieve even this, it's getting a mention.
Catch Me If You Can
Not really a comedy. I liked it though and it is an enjoyable 2 hours that I can't complain about.
I Spy
No one else would have this anywhere near a "best" list. I'm not everyone. I have always enjoyed Owen Wilson when he does his thing and Eddie Murphy embraced his tendency to play big without physically being being as he's been apt to do. Is the movie forgettable? Sure. Do I hate it? No.
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