1. Best in Show
Christopher Guest and Co. doing their thing. A true ensemble cast, filled with character actors who manage to be greater than the sum of their parts. The jokes are big but the delivery is grounded. The world is real and the characters fit in it, but not in the real world. Way to be cryptic, right?
2. Meet the Parents
Beginning in the year 2000, Ben Stiller began a quest for total world comedic domination that began with this simple but hilarious movie. The idea of "what if a Robert De Niro type is the over protective ex-CIA father of the woman you want to marry" is funny enough, but they took the idea, fleshed it out, and ran with it until you had a romantic comedy concept, stripped of the most of the pitfalls of the genre. That said, De Niro isn't quite as imposing these days.
3. Almost Famous
Not the third funniest movie of 2000, but a great movie that is generally considered a comedy (I call it a light-hearted drama, but whatever). When will Cameron Crowe make another movie that works this well? It also launched Kate Hudson into stardom and introduces the world to Zooey Deschanel on her slow climb to notoriety.
4. Scary Movie
I have never liked this movie series and my enjoyment of the Wayans Brothers' comedy stopped with the end of their TV show. That said, Scary Movie was a fresh (at the time) take on movie parodies (largely dominated by Mel Brooks for years). It was Anna Faris' coming out party as well. It's still weird that they opted to do a parody of a movie series that was already aware of it "Scary Movie-ness", but it worked well enough.
5. What Women Want
The world didn't always hate Mel Gibson. Before Jew-hating and...The Beaver, he was Mel "Fucking" Gibson. Academy Award winner, Mad Max, The guy who wasn't "getting too old for this shit". "Women" was a funny concept with a charming lead, not being asked to do that much comedic heavy lifting (except maybe when he's singing his favorite Meredith Brooks song). And, this is a rare movie in that almost no one has to delivery her funniest lines while the camera is on.
6. Miss Congeniality
The name says it all. How can you hate this movie? Humorous concept and a role Sandra Bullock pulls off with ease. It went for a lot of easy jokes, but only because that's what was asked of it.
7. I could not decide on a 7th movie. One could make a case for any of the honorable mentions, but my arbitrary criteria made it impossible to settle on one.
HONORABLE MENTION
Dude, Where's My Car?
Is this movie brilliant or absolute garbage? When watching movies that know they are bad (relish in it, in fact), it is hard to determine what is funny and what is bad. I always want to side on brilliant, but can't pull the trigger.
Charlie's Angels
At some point in the late 90s, someone decided TV shows from the 70s would make great movies. Some cases turn out better than others. This is one of the better ones. Opting to take the concept and make it their own, the producers made a movie that was funny, sexy, and exciting with just the right balance.
Me, Myself and Irene
Say what you will, but Jim Carrey commits fully to his characters. I'll say, more often than not, that works in this movie. Like most Carrey comedies, it completely relies on him to be funny since he dominates any room he is in.
Road Trip
A good R-rated teenaged quest movie, made unique primarily by Tom Green's presence, which serves as both a strength and a burden. Let's just agree he works best when not the lead.
Bring It On
PG-13 teen comedy. It is what it is. The jokes are never able to hit too hard. The story doesn't break formula. But, it gives you attractive cheerleaders dancing around. No complaints here.
Loser
I've always loved this movie more than it has a right to be loved. Not particular funny. Not particularly hip. Not even properly soundtracked (Punk girl's favorite band is Everclear. Really?). The cast is enjoyable and the story, straight of of the Billy Wilder playbook.
O Brother, Where Art Thou?
Good movie, but whenever the soundtrack is more popular than the movie (looking at you Garden State), I have a hard time cutting any slack.
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