Wu-Tang Clan's unofficial member Cappadonna was homeless at one point in his life. But here's the catch: While most rappers on this list lived on the street because they had no choice, Cappadonna made the conscious decision to live as a vagrant. “I was actually living in the street. It was by choice. But it was more of my way of rebelling against the materialistic world." That, and he was having issues with his wife, who also happened to be his manager. Tough times.