Lindsay Lohan

At the start of her career, Lindsay Lohan made a name for herself through roles on soap operas, in movies (especially The Parent Trap, where she played both twins, and black comedy Mean Girls) and as a pop singer. She has been involved in one form of the entertainment world or another since the age of four, and officially branched off into music in 2004 with her first single, "Rumors." Although clearly influenced by Britney Spears, Lohan sang with her own distinct style and seemed at first like she might remain a little closer to the Disney ideal than Spears. But before she even turned 21, La Lohan was making headlines for decidedly less G-rated activities: feuds with fellow young Hollywood royalty, a reputation for unreliability on movie sets, hardcore partying, stints in and out (and in and out) of rehab, her family of unabashed publicity hounds and a growing list of box-office bombs. By 2008, Lohan seemed to have (maybe) cleaned up her act (for the time being) and was getting ready to release her third studio album.