Comedy is an art. And likewise, I don't know art... but I know what I like. After forging through thousands of movies this list contains a lot of hidden gems, unheralded greats and a movies that simply hold a special place in my heart due to the circumstances in which I watched them for the first time. Memories. I've ranked these on how much I feel that these movies were specifically made for me. On to the movies!
10. Kung Pow: Enter the Fist
You don't have to love this, but you should appreciate the work that comedic powerhouse Steve Oedekerk (of Bruce Almighty, Evan Almighty and his breakthrough Thumb movies) puts into this movie. Instead of a straight up kung fu parody, Oedekerk purchased the rights to an old cheesy martial arts flick and then with the help of special effects and lots of hilarious dubbing, inserts himself and re-edits to create his own storyline. Under the loose plot of avenging his parents' deaths, The Chosen One sets of on a journey to kill Master Pain with many hilarious encounters including punching a hole in a guy (a perfectly round hole... I mean, is that even possible), a talking tongue, gopher-chuks, Neo-dun-dun-dun-sporin and many other great comedic moments. Certainly not for everyone, but if you've seen even one martial arts movie from the 70's or 80's you will appreciate the inside jokes throughout.
My Score: 8/10
IMDB Score: 5.8/10
9. A Guy Thing (2003)
I am truly perplexed as to why this has such a low rating. It has brand name stars in Jason Lee, Julia Stiles and Selma Blair. It has solid writing and jokes that work. It even has a romantic element that is believable and not crammed down your throat like a garbage Katherine Heigl movie. In fact, it is one of a few movies that could actually qualify as a romantic comedy for guys. Jason Lee plays a guy about to marry his perfect girlfriend (Blair) when he meets a charmingly imperfect waitress at his bachelor party (Stiles). Great date movie that guys can actually make it through.
My Score: 8/10
IMDB Score: 5.5/10
8. Kissing A Fool (1998)
Jason Lee again (man, people really don't like this guy) plays Jay, the nerdy, unsuspecting best friend of Max, a popular Chicago sportscaster played by David Schwimmer. Jay, a writer, introduces his editor Sam (Mili Avital who has been doomed to indie movies and spots on TV here and there) to Max. They hit it off and quickly get engaged, but when Max suspects that she would cheat on him, he puts his best friend Jay up to the task of trying to get her to falter. Awkward hilarity ensues. As an indie film, I think this is another case of good writing, genuine emotion but not enough star power or budget to sway the masses.
My Score: 8/10
IMDB Score: 5.4/10
7. Josie and the Pussycats (2001)
At first glace many will dismiss this film as a kids movie, a straight adaptation of the musical comic book trio. That assumption would be wrong! For those not familiar with Harry Elfont and Deborah Kaplan, they are a writing/directing duo who had a streak early in their career when they gave their own unique spin on familiar childhood classics like The Flintstones and The Brady Bunch - which I'll mention later - but you'll probably recognize their style from their cult classic Can't Hardly Wait. They successfully used their opportunity to adapt this comic and turned it into an all-out parody of consumerism in America this an advertisement in almost every scene. With a quirky, fun screenplay and a great cast, that is enough to make an entertaining movie, but even more impressive is the spot on soundtrack written by Anna Woronker - of the, sadly, now defunct band That Dog. This movie hits every note for me!
My Score: 8/10
IMDB Score: 5.1/10
6. The Third Wheel (2001)
This independent movie is really a tiny, niche movie packaged as a mainstream comedy - which is why I think this movie's reviews have suffered. The movie features Luke Wilson as a shy office worker who finally builds up the courage to ask out his dream woman (Denise Richards), but on their first date it seems that everything goes wrong. Just when they leave for their date they hit a homeless man (played by the underrated writer of the movie Jay Lacopo) who Wilson feels he needs to help to impress his date, but he ends up tagging along for the entire night. Successfully a screwball comedy that is leveled out with real emotional connection and some surprisingly touching moments. Also stars Ben Affleck in a supporting role and includes a cameo by buddy Matt Damon.
My Score: 8/10
IMDB Score: 5.4/10
5. Slackers (2002)
Immediately during the opening credits when I heard the orchestral rendition of The Who's "Baba O'Riley", I knew that this movie was special. From a realistic perspective, this is really just another raunchy college comedy about a boy (Devon Sawa) who likes a girl (Jamie King) who is being stalked by another boy (Jason Schwartzman). Admittedly, this resounded so much more with me because when I saw this movie, I was that boy (and arguably that stalker) who was trying to get that girl to notice me in college. It became sort of my theme movie. Objectively, I still think this movie doesn't get the respect it deserves as the jokes are funny - even if the plot is a bit uneven - the acting is decent - more than decent for Schwartzman - and the music is amazing - including a college band version of the Ace of Base classic "The Sign". I always felt like it was made just for me... and the ratings seem to agree.
My Score: 9/10
IDMB Score: 4.9/10
4. A Very Brady Sequel (1996)
Another film written by Harry Elfont and Deborah Kaplan, who do a great job of creating both an homage and a parody of the classic TV series. The general story involves a man who shows up and claims to be Carol Brady's first husband, but is actually a con man looking to steal the Brady's familiar horse statue which is actually an ancient artifact worth millions. They highlight situations from some of the most popular episodes, but the real humor comes from capturing the "aww shucks" spirit of the show, but inserting far more witty jokes - including some sexual tension between Marcia and Greg. Don't write this off as a straight copy of the original show, there is much more to be enjoyed here. I'm convinced that fans of the show were put off by the new take on the American family and may explain the crappy ratings.
My Score: 8/10
IMDB Score: 5.3/10
3. Freaked (1993)
This movie was far overlooked and (not to sound like some sort of movie hipster, but...) you've probably never even heard of it - until now. Alex Winter (the other half of Bill & Ted) "stars" as a PR rep for an evil corporation on his way to South America to prove that a component in many of their products isn't as toxic as the media claims. Accompanied by his crass best friend and a reserved environmentalist, they take a detour to see a freak show... but end up becoming the freaks. This silly comedy has a surprising amount of recognizable faces, but it is really the all-out insanity of the whole thing that brings the laughs. Much better late at night, even more so with a group of friends and especially after a drink or four.
My Score: 8/10
IMDB Score: 5.6/10
2. Pootie Tang (2001)
Another movie that hit the bargain bin right out of the gate, this is one of comedian Louis C.K.'s only narrative scripts to see the light of day (the other being another underrated comedy Down to Earth). There is no way I can justify this movie to everyone... either you get it, or you don't. So I'm just going to shoot straight. A character born from The Chris Rock Show, ghetto superstar Pootie Tang fights crime and lays down beats all the while communicating in his own indecipherable slang (which many will find annoying... I find hilarious). Pootie takes on evil corporate America, but becomes a slave to them before ultimately redeeming himself. The story isn't the point, it is the WTF moments and silly skit-like scenes that had my laughing all the way through. Again, not for everyone - not even most Louis C.K. fans - in fact for almost no one. But I'm certainly one of the few.
My Score: 8/10
IMDB Score: 4.5/10
1. Scary Movie 2 (2001)
Many parody movies from the past few years like Epic Movie, Date Movie, etc. just get lumped together by audiences, which I think is the first explanation for this movie's low ratings. The second is that with any parody movie, if people don't understand where the jokes are coming from they probably won't find them funny. Though I didn't care much for the first in this series, the Wayans brothers took the second to a different level. Growing up on the show In Living Color, I immediately connect with their writing style and jokes. Seeing almost every horror movie ever made and truly understanding the genre, every joke made sense. Although the humor is often juvenile, you can tell the gags are well thought out with multiple comedic beats instead of the one beat humor of 99% of other parody movies. I ranked this as number one because of the specific horror & comedic experience going into this, truly makes it a niche movie that is lost on too many viewers.
My Score: 9/10
IMDB Score: 4.8/10
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