Clueless
1995

Clueless is a comedic masterpiece. Under the thoughtful direction of Fast Times' Amy Heckerling, Alicia Silverstone is sold gold-- and she doesn't look like she has a beard. Way better than the Gwen Paltrow movie based on the same novel, Clueless features perhaps my all time favorite movie line: Alicia's character on selecting her first lover: "Dion, you know how picky I am about my shoes and they only go on my feet."

Black Narcissus
1947

This movie is not generally regarded as Powell and Pressburger's best, but I think its superior to Red Shoes. It's the tale of some nuns on a mountain and the way their psychological condition completely breaks down. The transformation of Sister Ruth from nun to sexual vixen / murderess is pretty surreal. Also, the film features the most beautiful photography of all time and the most brilliant closing shot ever.

Spice World
1997

When the Internet first came out, one of its best uses was trashing the Spice Girls. But since I always end up being a fan of the heels, I became, I'm ashamed to admit, a particular type of Spice Girls fan. While you might think a film like this might make it on the "so bad it's good" list, I found Spice World to be quite fun on its own merits, which include having the girls themselves act sarcastic about their success. Should have been released under its original title, It's Been a Hard 15 Minutes. Girl power!

Josie and the Pussycats
2001

In a similar vein to Spice World, this movie appears even less appealing at first glance, since there's nothing intrinsically ironic about this movie. Yet, despite a poor-de-force from cracked-out Tara Reid, this movie manages to muster up quite a bit of charm and levels some scathing jokes at pop culture. Any movie that gets Carson Daily to admit to participating in a corporate conspiracy to control the minds of the youth of America is an alright movie by me.

Ghost World
2001

It's probably not exactly accurate to put this movie on this list because it's got quite a bit of critical credibility. Still, the real star of the show isn't Thora Birch but rather Scarlett Johansson's Rebecca-- who is amazing and hilarious in her monotone approach to life. And her character's growth in the film is the more naturalistic of the two. Plus, you know, she's hot.

Honorable Mentions:
Legally Blonde (2001) - Good, but not quite as good as you'd think it is given that it just sorta steals the whole idea from Clueless. I have high hopes for the sequel, though: Red, White and Blonde.

Charlie's Angels (2000) - No one saw this one coming, but everyone pretty much realizes now how much better it is than it has any right to be. Alas, the sequel to this one will probably suck.