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Five days before Leif Garrett turned 18, he crashed his car and rendered his friend Roland Winkler paraplegic. Winkler’s family sued Garrett for $25 million for gross negligence; they settled out of court for $7.1 million. That was only the start of the onetime teen idol’s troubles: In 1999, he was arrested for buying narcotics from a narc; in 2006 he was arrested for not having a subway ticket and drug possession. Then in February 2010, he was arrested for having black tar heroin in his shoe. He’d go on to appear on “Celebrity Rehab with Dr. Drew” later that year. (Photo by Pacific Coast News/Everett Collection)
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