When Ol' Dirty Bastard leapt into pop culture consciousness on the Wu-Tang Clan's 1993 debut Enter the Wu-Tang (36 Chambers), boasting "Beetle Bailey rhymes" like "I'm cherry bombing shits, boom!/Just warming up a little bit, vroom vroom," it was clear he either on drugs, or just insane. Not to take away from his skills and artistry, but as the events of the next decade revealed, it was a bit of both. 

More than that, the idiosyncratic, reductive nature of his songwriting and worldview, combined with his limited discography (he released just two terrific solo albums during a decade when most other rappers glutted the market with product), made him a living legend. The problem was his life itself was out of control. He had seven children; Wu-Tang leader RZA said he once witnessed Dirty force his son to watch him use drugs.

According to the FBI file on the Wu-Tang Clan, ODB was arrested nine times between 1987 and 1999 for crimes ranging from petty larceny (he tried to steal a $50 pair of shoes while carrying $500 in cash) to attempted first-degree murder. In the last six years of his life, he continued to be arrested frequently for drug possession (he was once caught with marijuana and 20 vials of crack cocaine and reportedly asked the cops to "make the rocks disappear"). He didn't tone it down for his many court appearances on drug charges; he once asked a female prosecutor "Do I make you horny?" before falling asleep in court.

In 2000 he escaped from court-mandated rehab and attended a record release party for the Wu-Tang Clan's third album. Within a month he was caught and sentenced two to four years in prison. He regained his freedom in 2003 but was too damaged to survive much longer. In November 2004 he died of an overdose of cocaine and the prescription drug tramadol.