Here's how he got to where he is today.
The lanky lyricist grew up on a diet of Michael Jackson and Tina Turner, but when he got older, his tastes widened to include everything from the Beatles to Björk.
That range wasn't necessarily evident on his early productions, but his woozy "Cloud 9" proved to be an underground gem that garnered the attention of key music industry folks, including T.I. and Atlantic Records; the Atlanta upstart is signed to that label through Tip's Grand Hustle imprint.
B.o.B had been championed as an heir to OutKast's Andre 3000 after he released a slew of mixtape material in the past few years that earned him a solid reputation within the hip-hop community. "I'll Be In the Sky," "Haterz Everywhere" and "Lonely People" were among the notable numbers from his street projects, which include the DJ Smallz-helmed Cloud 9, Who the F--- Is B.o.B and B.o.B vs Bobby Ray, which was backed by DJ Green Lantern and Don Cannon.
As he sat in an incubation stage, however, B.o.B soon found himself at the center of swirling rumors last year that he was quitting the music biz before his first album could be released.
But that turned out to be a small speed bump on his road to pop stardom. In 2010, the eclectic rapper — who late last year announced he would also go by his birth name, Bobby Ray — found everything finally coming together for him.
His Bruno Mars-assisted "Nothin' on You," with its saccharine-sweet vocals and flirtatious verses, shot to the top of the Billboard Hot 100. His debut album, The Adventures of Bobby Ray, took a similar path, debuting at #1 on Billboard's albums chart.
His single with Paramore's Hayley Williams, "Airplanes," was a top five hit and his collaboration with Rivers Cuomo, "Magic," just entered the top 10. And after opening for Jay-Z and Eminem on Thursday (September 2) night, it seems like B.o.B can do no wrong these days. He earned a total of five VMA nominations: Best Male Video, Best Collaboration, Best Hip-Hop Video, Best Pop Video, and Video of the Year.
We bet B.o.B will tell you himself that it pays to play different.
Do you think B.o.B will take home some hardware on September 12? Let us know in the comments!
The 27th annual MTV Video Music Awards will be broadcast live from the Nokia Theatre in Los Angeles on Sunday, September 12, at 9 p.m. ET.