Occupation: Model

The late Anna Nicole Smith was always a bad girl with a heart of gold. The blonde bombshell dropped out of high school and then married the oil business mogul, J. Howard Marshall, who was 62 years older than her, which inspired a lengthy trial over the estate between Smith and Marshall's son. She was addicted to prescription medications and often appeared drunk or on drugs at red carpet events, like at the American Music Awards in 2004.