8. Celebrity: Lil’ Bow Wow
Clothing line: Shago
Launch date: 2003
Fail date: 2006
Reasons for the fail: Velour track suits, anyone? We’ll give him a lil’ credit ‘cause he was 16 at the time, but Lil’ Bow Wow’s line —with collection names like Classic, Knight, and Racing—suffered from the same identity crisis and growing pains that caused him to leave the “Lil’” behind.