#9. Drake (25)
You might know him as Aubry Graham, Drizzy or, for Degrassi fans, Jimmy Brooks. Perhaps his "Motto" of YOLO (You Only Live Once) is the secret to his success. His 2010 debut album Thank Me Later found love on the Billboard chart, debuting at #1, as did his follow-up LP, Take Care. Currently Drake is behind an album of Aaliyah tracks, and so on top of the world that for his recent "HYFR" music video, he threw himself a second Bar Mitzvah.