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Ol' Dirty Bastard

One of the founding members of the Wu-Tang Clan, who recorded some of the most influential hip-hop of the '90s, Ol' Dirty Bastard was the loose cannon of the group, both on record and off. Delivering his outrageously profane, free-associative rhymes in a distinctive half-rapped, half-sung style, ODB came across as a mix of gonzo comic relief and not-quite-stable menace. Unfortunately, after launching a successful solo career, his personal life began to exhibit those same qualities. ODB spent much of 1998 and 1999 getting arrested with ridiculous, comical frequency, building up a rap sheet that now reads not so much like a soap opera as an epic Russian novel. At first, his difficulties with the law made him a larger-than-life figure, the ringmaster of rap's most cartoonish sideshow. Sadly, his life inevitably slipped out of control, and the possibility that his continued antics were at least partly the result of conscious image-making disappeared as time wore on. It was difficult for observers to tell whether ODB's wildly erratic behavior was the result of serious drug problems or genuine mental instability; bad luck certainly played a role in his downfall, but so did his own undeniably poor judgment. Despite being sentenced to prison on drug charges in 2001, it's worth noting that while he was running amuck Ol' Dirty's offenses were largely nonviolent; the saddest part of his story is that, in the end, the only person he truly harmed was himself.