In addition to Clueless (based on Jane Austen’s Emma; that explains it!), I was totally surprised at how much I loved a dumb little movie called Idle Hands. It’s completely what it’s billed as: a slacker gets possessed by a demon; hilarity ensues … but lordy it’s funny! I came across it on HBO or something and fully expected to turn it off in five minutes. I watched the whole thing. The ending is weak, as I recall, but really the premise as carried out here is hysterical.
I was surprised how much I liked Bring It On. I caught the beginning of it on cable, and started to watch it for the laughs, but I couldn’t stop. It was hilarious and actually kind of deep . . . for a Kirsten Dunst movie, of course.
And yeah, Stranger Than Fiction was awesome. SDMB reviews convinced me to Tivo it, and wow! Give Will Ferrell a script that wasn’t written by college stoners, and he can fucking act! He’s supposed to be pretty intelligent in real life, and it comes through in this movie.
Anybody going through my DVD collection inevitably rolls their eyes at Sugar and Spice. Hmmmm, I wonder what the single middle-aged guy is doing with this cheerleading movie? Actually, the movie is damn good, with plenty of sharp, smart comedy, and anybody I’ve managed to tie down and force to actually watch the film has agreed.
Or maybe. ya know, being tied down, they think it’s in their best interest to agree? 
I’ve not seen that movie, but my daughter liked it. Of course, she was a cheerleader in middle school, so who knows?