"It popped off for me right at a point when I was finna quit," B.O.B said to Fader in 2007, speaking about the song "Cloud 9." "I was about to get a job at the mall, man." Thankfully he didn't, and he hit the scene as a fresh face in an era when it seemed like every 20-something had a dollar, a dream, and a microphone.

What was so impressive about Bobby Ray back then was his mic skills more so than his singing or crossover appeal. He was a straight up spitter who supplied a distinct flavor of Southern consciousness, obviously influenced by ATLiens like Outkast. Years later, and two crossover albums after the fact, it's important to remember the natural talent that Bobby Ray had before the Billboard hits. —Insanul Ahmed