30. Charles Hamilton
Interscope Records, the most prominent rap label in the 2000s and home to Dr. Dre, Eminem, and 50 Cent, had finally found the next cornerstone to their franchise, a formerly homeless young man from Harlem named Charles Hamilton. Charles seemed to have all the pieces in order: a very interesting story and point of view, the same powerhouse lawyer as 50 and Eminem, the same A&R who was involved with Kanye and Soulja Boy, a co-sign from DJ Skee, a viral video where he held his own freestyling with Game and Ye, a rapidly growing buzz online, and what many labeled sheer genius.
After releasing two handfuls of mixtapes during the summer of 2008, and on the eve of debuting music from his first album, a series of events over the course of just a few months caused the house of cards to fall apart. Charles claimed he was dating Rihanna. Charles lost in a rap battle at Penn State. On camera. Charles made fun of his girlfriend's abortion and she punched him in the face. On camera. Charles gave J.Dilla executive producer credit on his album, having had no discussion with Dilla's family or estate, and stirred up a great deal of anger from the city of Detroit.
Charles was dropped from Interscope. Charles was arrested in Ohio. Charles took to a wheelchair and was hospitalized for mental reasons. Four years (and an Internet lifetime) later, Charles is attempting a comeback. On his own.