7. Ma$eMa$e reached the height of his popularity as a part of Puff Daddy's Bad Boy Records and was never more relevant than he was when dancing alongside Diddy in the music video for "Mo Money, Mo Problems." If that sentence doesn't depress you, you're probably the type of person who watches Schindler's List twice in a row. But Ma$e left the music industry in 1999 to pursue "a higher calling," becoming a minister so that he could lead his fans away from the "path to Hell" he thought he'd put them on. But evidently G-O-D was satisfied with Ma$e's penance after only five years, because that's how long it took him to leave the ministry and go back to music, although this time he rapped clean and awkwardly inserted Christian messages into his songs. Dubbed the "Bad Boy gone clean," Ma$e and his return album, Welcome Back, couldn't replicate the success he had as a "Bad Boy still dirty," and went back into the shadows almost immediately, largely due to some contractual issues between him and Diddy. It was a short-lived, spiritually unsatisfying return. He's been toiling away on mix tapes ever since, though he's supposed to be releasing a new album in 2015. Hopefully this comeback will stick.