Lil' Bow Wow
Then: By the time he was 16, Lil' Bow Wow dropped 3 rap albums. Around the same time, he made his film debut starring in Like Mike. In 2011 the rapper revealed he has a child.
Now: He dropped the "Lil'" since he's not so lil' anymore, but eventually began going by his real name, Shad Moss. He's working on a new album, Underrated, and plays Brody Nelson in the CSI spinoff CSI: Cyber. He's currently engaged to TV Personality Erica Mena.
[Photos via @bowwowbrazil and @bowwowbrazil]