44. Amy Whinehouse
Winehouse had an incredible talent that the world will miss, but her career was imbued with her battle with substance abuse and her struggle with violent mood swings. She cancelled a number of shows in the UK in 2007, blaming exhaustion, and was later hospitalized for an overdose of heroin, ecstasy, cocaine, ketamine and alcohol.
Beyond that, Winehouse had a number of run-ins with the law, namely for punching a fan in the face, getting arrested for marijuana possession in Norway, and being taken into custody when a video of her, supposedly smoking crack cocaine, was given to the police.