I'm such a sheep - I'd have to go with Very Bad Things and Heathers, too.

I just remembered Death to Smoochy!
I really liked this recent black comedy, much more than I expected too.

curdled, last supper, i married an axe murderer, and serial mom are my favorites....

anyone on here seen the movie "the secretary" ??? it is dark and very comedic in away... I love this flick.. and I have to say those ass spanking scenes are mighty delicious.. I dont know that actress` name but she is hot...

idle hands, cable guy are my favs

Maggie Gyllenhall...Donnie Darko's sister. In real life and the movie.

I havent seen her in any other movies just I was up one night late and I saw this movie on and it caught my eye... she is a down to earth type of girl ya know what I mean... man through out the movie she started changing and turning into this very sexy attractive woman ... I actually bought this movie the next day after seeing it, just because of her.. the movie is good too.. :D

I liked "hexed" and "the dream team", although they were only borderline dark...

Hexed is an awesome movie... glad you mentioned it..

Jawbreaker, with Rose Mcgowan was pretty dark and funny. A newer 'heathers' type of movie.