Age: 29
Label: Wicked Awesome/Republic
From: Cleveland, Ohio
Active Since: 2003
Latest Release: Indicud
Recent Single: "Just What I Am"
Four years since Scott "Kid" Mescudi came on the scene with the likes of Ace Hood, Asher Roth, B.O.B., and Wale, it’s difficult to put him in context with his peers. Cudi’s career has taken enough twists and turns to make him the most complicated artist on this list.

After his two albums, 2009’s Man on The Moon: End of the Day and 2010’s Man on The Moon II: The Legend of Mr. Rager, combined to sell more than a million copies, he took a hard left, flouting hip-hop norms with WZRD, a rock collaboration with longtime friend/producer Dot Da Genius, and the experimental, self-produced Indicud. Is it rap? Is it rock? No, it’s just an artist following his muse, concocting tracks to the beat of his Maschine drum pad.

One thing that’s for sure is that Cudi has a rabid fan-base. With virtually zero press or radio play, Indicud sold 140,000 copies its first week. Are his moves puzzling at times? Yes. But in recent years, Cudi has put straight up "rapping" on the backburner to focus on other ventures like acting, producing, and rocking out. So the next time you find yourself scratching your head, just know it’s all part of the method to Cudi’s madness. —Joe La Puma

RELATED: Born Again: Kid Cudi Talks Making Indicud, Leaving G.O.O.D. Music, and Where He Goes From Here