The question of identity informs much of his music catalog, mainly the dichotomy of B.o.B—the battle-rapping upstart who snaps into beat mode even on throwaway remixes like Cali Swag District’s “Teach Me How to Dougie”—vs. the free-wheeling, guitar-strumming Bobby Ray, who seems born to marry a pop melody. And there’s another dichotomy at work here: the idea of simultaneously being an artist and an employee—and being okay with that. Or not.
“I checked my Web site one day and I was like, ‘Damned, I’m selling earbuds now,’” he says, shrugging off any sense of betrayal by his corporate bosses. “Don’t get me wrong—basically they ask me what I want. Some of it can’t work. Like, I wanted to have my own rolling papers, but in the grand scheme of things that probably wouldn’t have been the best idea,” he says with a laugh. “You have as much say as an artist as you want to have—and as far as the contract will allow. I’ll say that.”
THE SON OF A PASTOR WHO broke away from the church, Bobby Ray learned the art of moving bodies and letting loose messages at an early age. “Watching him deliver a point, that influenced me lyrically,” says B.o.B. “Even performingÉ just the way that I visualize the stage and how the music should be presented. You know, church musicians, they get down.”
By the first grade, Bobby was taking trumpet lessons, while his sister, who’s a year and a day his junior, took piano lessons. “My sister got better at the piano than I did at the trumpet,” he says. “So I learned from her to play piano—I’m actually better at piano now than I am at the trumpet.” Today, he also plays the French horn, guitar and percussion. And when nothing else is available, he’ll play coffee mugs.
Describing himself as an “extremist” who takes things too seriously, B.o.B admits to being something of a conspiracy theorist. “I was one of them kids who was like, ‘You know there’s people doing stuff you don’t even know about,’” he says. “I’d be on the Internet all day, looking up ghosts and aliens and stuff that would completely terrify me, but I wanted to research it. That kinda started me on this rabbit-hole chase, just trying to find answers. That’s every teen—trying to find answers, whether it be socially or just with subjects. After a while you realize it’s only a certain amount of people that realize how much of what we do is what we’re conditioned to do. When you realize that, it’s like, ‘Okay, you can sit here and research this all dayÉ What are you gonna do about it?’”
The next step was obvious. I’ll just rap, he recalls thinking. “I was like, ‘I been rapping for some years now, I’m in high school, I feel like I can take what I know and help antidote it with lyrics.’”
Then in 2006, he produced “Da Cookieman” for local Slip-N-Slide artist Citty. The song was forgettable, but the experience played a significant role in B.o.B’s life, as summed up on “My Story” from his first mixtape, Cloud 9, released in 2007: “Then I sold my first beat, got a couple stacks/And, just like a nigga, man, I spent it like that/Got a couple diamonds, got a couple hats/And filled up my closet with some shoes and some slacks/Now I’m back to square one, where I’m at now/Rapping in this booth in the basement of a house.”
His performance in a talent showcase at T.I.’s Club Crucial got him noticed by industry player TJ Chapman, who signed on as his comanager and introduced him to Jim Jonsin. The producer of Lil Wayne’s “Lollipop” made B.o.B the first artist signed to his Rebel Rock venture through Atlantic Records. This was October 2006, and B.o.B was in his first semester as a senior in high school.
He decided to drop out, but maintains that his diploma is “still in the works.” About a year later, T.I.’s Grand Hustle also signed on as one of his label backers. The King of the South’s cosign gave B.o.B’s image credibility and grit. For an artist who admits to having had the latest album by French alt-rockers Phoenix on repeat in his car, names the U.K. indie rock collaborative Florence and the Machine as his favorite new artist and tends to veer off into meaning-of-life raps over guitar riffs, the T.I. connection made him seem a little more Wyclef, a little less Hootie without the Blowfish.
“One of our elaborate discussions was about whether or not he should cater to more so an ‘urban’ audience,” T.I. shared with VIBE, shortly before returning to jail for parole violation. “My response to that was, ‘Well, how much do you care about the urban audience?’”
Early on the answer was obvious. Equal parts goofy and gully, B.o.B’s second mixtape, 2007’s The Future, found him speaking on quotidian street themes: riding Chevy’s, hating haters, sometimes loving hoes, smoking weed and shouting out his city. Though his first two tapes showcased the type of musicality that would later become his signature—along with Sam Cooke and Curtis Mayfield, source material ranged from the Beatles to the White to The Little Rascals theme song—his lean was decidedly street. Or not. As T.I. aptly described, B.o.B was “urban in the sense of when Andre 3000 decides to rap—as urban as that may be.”