Chronology of Celebrity Crushes

1994: Lisa Loeb


Long before Tina Fey made glasses cool, Lisa Loeb was the posterchild for nerd-chic. She won over so many hearts with her video for "Stay." Including mine. And probably Ethan Hawke... he discovered her, got her song on the Reality Bites, and directed the "Stay" video. I'm guessing they were more than just "friends."

Post-"Stay" thumbs-up: 16 years later, she looks almost exactly the same. Plus she's still a credible, if not commercially-viable, artist.


Post-"Stay" thumbs-down: Her albums don't sell a damn thing. And despite a clever title, her reality dating show #1 Single was kind of a disaster.

Thumbs-up story: One of my good friends went to Brown University with Lisa, and I got to meet her at his birthday party a few years ago. She and I spent a good hour talking, during which time she laughed at my jokes, seemed impressed that I wrote for Cash Cab, and compared me to Duncan Sheik (which is a good thing in her world). I really thought I was in the midst of a successful woo...

Thumbs-down story: Until her boyfriend (now husband) showed up at the end of the night to take her home on his motorcycle. Bah!