Beauty of the Day: 5 Secrets of Joan Smalls' Style
Then: Known for playing a child prostitute at the age of 12 in Pretty Baby. At 14, she appeared in provocative Calvin Klein Jeans print and TV ads. She was also married to tennis sensation Andre Agassi for two years in the 1990s.
Now: The Princeton grad wed Chris Henchy in 2001, has two kids with him and is a working actress with TV, movie and Broadway appearances under her belt. In July 2016, she organized her very first art exhibition with the New York Academy of Art.