He's been in over 50 movies, but rarely as the lead. He's good friends with John Cusack, who I am moderately obsessed with. (It's a tie between him and Jon Stewart). Here are my favorite Jeremy Piven-featuring films.

5. Very Bad Things
Okay, so I probably shouldn't like this movie. It involves a bachelor party gone wrong, a cover-up and other not-so-funny themes, yet this movie makes me laugh. I am truly a sick individual.

4. Grosse Pointe Blank
In this movie, Piven plays Paul, a pot-smoking real estate agent who is reunited with Martin (John Cusack), a hit man returning for his high school reunion.
Favorite line:
Martin: Debi's house.
Paul: Kinda crept up on you, didn't it?
Martin: No, you drove us here.
Paul: [pause] Yep.

3. PCU
Finally, a lead role (in an overlooked college movie about political correctness at its worst). Piven plays Droz, the leader of students who live in 'The Pit'.
Favorite line (which is oft-quoted at our house):
Droz: What's this? You're wearing the shirt of the band you're going to see? Don't be that guy.

2. Cupid
I'm bending the rules a bit; this is not a movie. Cupid was on for one season (ABC), and its cancellation rates right up there with My So-Called Life's on the "I can't believe they cancelled this show; if only the WB was around back then" list. Piven played a possible mental case who believed he was Cupid.

1. Say Anything
In one of the greatest movies of all time (completely uncontested), Piven plays Lloyd Dobler's (John Cusack's) friend Mark.
Favorite line:
Mike: I don't know you very well, you know, but I wanted to ask you - how'd you get Diane Court to go out with you?
Lloyd Dobler: I called her up.
Mike: But how come it worked? I mean, like, what are you?
Lloyd Dobler: I'm Lloyd Dobler.
Mike: This is great. This gives me hope. Thanks.