Brittany Murphy was four years removed from her breakout role in Clueless when she signed on for a role as Drop Dead Gorgeous pageant contestant Lisa Swenson — and like many of her fellow cast mates, it was just one of multiple projects she did that year. For Murphy, her turn as a psych ward patient in Girl, Interrupted got far more attention at the time. And for several years afterward, she was a regular presence on the big screen — first playing the supporting best friend role to a more established star (e.g. Drew Barrymore in Riding in Cars with Boys), later anchoring romantic comedies like Just Married and Little Black Book, and eventually doing a gritty turn opposite Eminen in 8 Mile. Sadly, Brittany Murphy's career came to an abrupt end in 2009, when she died of pneumonia at age 32.