B.o.B, who was only 17 when he signed his first major-label record deal, was still unique. His borderline eccentricity and artistic mind, belied by his music's conventional Dirty South appeal, raised his stock above the many copycat Southern up-and-comers and, of course, welcomed comparisons to OutKast and, specifically, their offbeat half, André 3000. Although he grew up on the east side of Atlanta in Decatur, Bobby Ray Simmons was born in North Carolina on November 15, 1988. Creating music became an early hobby for the young talent, who played trumpet and other instruments throughout grade school. By the time he was in high school, he already had management and had formed a production duo called the Klinic. At age 15, he even successfully sold a beat of his own to Slip-N-Slide recording artist Citty. When his partner left for college, however, B.o.B decided to take the solo artist path and subsequently recorded the hazy, spoken word-like ode to marijuana "Cloud 9."
In 2006, B.o.B's manager helped sneak him into Club Crucial (owned by Atlanta rap star T.I.), since he was underage, and the teenage MC wowed the audience with his self-produced ode. A part of that impressed crowd, producer and industry veteran TJ Chapman agreed to co-manage B.o.B, which only a month later led to B.o.B's signing with Atlantic and subsidiary imprint Rebel Rock, run by Florida producer Jim Jonsin (Lil Wayne, Trick Daddy, Jamie Foxx).

His first single for Atlantic, Haterz Everywhere (2007), showed lots of promise, reaching the Top Five of Billboard's Bubbling Under R&B/Hip-Hop singles chart. Before long, several outlets and publications, including XXL, Spin, and MTV, took notice of the Atlanta rapper, running "Artist to Watch" features and tagging him as the next Atlanta rap artist to blow up nationally. B.o.B's second single, "Grip Your Body," guested by British soul siren Amy Winehouse, also fared well. He kicked off 2010 with a series of singles, including “Airplanes” with special guest Hayley Williams of Paramore and “Nothing on you”. These tracks landed on his debut album, The Adventures of Bobby Ray, released that same year.