Current age: 34
Career at 20: In 1999, Claire was studying at her dad's alma mater, Yale University, before eventually dropping out the following year. With Romeo & Juliet and her Emmy-nominated days on My So-Called Life behind her, she appeared on the big screen multiple times in 1999 with roles in The Mod Squad and Brokedown Palace.
Relationship status at 20: She was linked to Australian singer Benjamin Lee, whom she dated from 1997 to 2003.
Quoted at 20: During an appearance on David Letterman, Claire opened up about her break from acting, saying, "I've just been going to school, and, you know. I just finished my first year at Yale, which was a huge relief. It's really rigorous, but there's some fun to be had."