Taken in by Lionel Richie, who was a friend of her parents, when she was 3 and adopted officially six years later, Nicole Richie grew up extremely privileged, well connected (Her godfather is Michael Jackson.) and wild. She used fake IDs to sneak into clubs by 14, experimented with drugs and eventually dropped out of University of Arizona. After being busted with a balloon of heroin in 2003, she checked into Sierra Tucson rehab. Later that year, she started filming The Simple Life, a fish-out-of-water reality show with her friend since kindergarten Paris Hilton, on an Arkansas farm. The show was a huge hit and the scary skinny socialite was on board for four more seasons although a two-year feud with Hilton meant filming season 4 separately. She parlayed becoming a household name into a book deal (2005’s The Truth About Diamonds), modeling gigs like being the face of Jimmy Choo in 2006, a jewelry line (House of Harlow) and a mentor gig on NBC’s Fashion Star design competition. After a 10-month engagement to the late DJ AM in 2005 and a relationship with childhood friend Brody Jenner in 2006, she took up with Good Charlotte singer Joel Madden in 2007. While pregnant with their first child, daughter Harlow, Richie was sentenced to four days in jail for her second DUI arrest in 2006. She gave birth to their second child, son Sparrow James, in 2009, and they tied the knot officially in December 2010.