Top Comedy Movies of 1999

I really was going to start in 2000, but 1999 had such a strong crop I couldn't leave it out. Seriously, I don't know if there is a stronger year that I cover.

1. Office Space

Forget The Office. This was the original "my work sucks" movie [of this generation]. Endlessly quotable. Oddly, it made careers for almost no one. How happy is Jennifer Aniston though that she latched on to this project? That's given her years of goodwill for every Rumor Has It... she's made since.

2. Dogma

Arguably Kevin Smith's biggest experiment. Featuring a strong cast that has only gotten stronger since. Brilliant commentary without feeling forced and also manged to blend action into what still would've worked fine as just a pure comedy. Maybe my favorite Chris Rock roll ever.

3. American Pie

Can we say "game changer"? Basically everyone in this cast went on to have successful movie or TV careers. It also marked the return of the R-rated teen comedy of the 80s. And, let's not forget it introduced the world to the MILF.

4. Galaxy Quest

Where the hell did this movie come from? Screenplay by David Howard who has done nothing before or since. This was a brilliant parody of Star Trek but still managed to be a full movie in it's own right. It's also refreshing that it opted not to take the Mel Brooks style, absurd, in-your-face jokes. Alan Rickman's second movie on this list this year. Just saying.

5. Austin Powers: The Spy Who Shagged Me

I have never been a huge fan of the series, but it's quality is undeniable. And, I'm not overstepping to say this is the best of the series. It introduced the world to Verne Troyer's "Mini Me", which I'm calling a good thing. Heather Graham is a total upgrade from Liz Hurley. Make note of this because you won't be seeing many sequels on the Top list.

6. 10 Things I Hate About You

On the surface, what we have here is a standard teen movie, and in many ways, it is. Take a closer look and you have a terrific young cast (Yeah, there's an Oscar winner in the mix) surrounded by an extremely strong adult supporting cast in the background. And yes, dead Heath Ledger helps get this into the list.

7. South Park: Bigger, Longer, and Uncut

Has it really been a dozen years since this came out? South Park is now in it's 15th season, determined to outlive the Simpsons. And let's not forget the Academy Award nomination. The movie made great use of the show's style and brand of humor in moving it to the big screen. Making it a musical added that little something extra it needed.


 HONORABLE MENTION


Notting Hill
The closer Hugh Grant stays to England, the funnier he is. Call it home court advantage, but this movie reaches a level that all his RomComs since have failed to reach.

Being John Malkovich
A great movie for "What the fuck?" laughs. It's not a movie that you laugh at the jokes as much as you randomly chuckle while watching as you reflect on how bizarre it is.

Big Daddy
Oh shit, Adam Sandler realized he is getting too old for the overgrown child schtick. Let's fix this by pairing him with an actual child. Phew, that was close...Still, funny in a much calmer manner than Sandler normally aims for.

Never Been Kissed
It's a shame Drew Barrymore spent her actual high school years high as shit, because her bubbly demeanor was made for a good high school comedy. Maybe a little too watered down, but this has just enough laughs to keep it from being a date night bust (Certainly more enjoyable from a man's perspective than The Notebook).

Life
Matrin Lawrence and Eddie Murphy, two stars that have spent the last 20 years going all out with their comedy and largely falling flat doing so. "Life" is not the funniest movie either man has done by a lot (ok, not Eddie's funniest), but it is a departure from either's standard fare and a breath of fresh air from both.