The Evolution of B.o.B

Don't miss B.o.B. tonight on 106!

"Headband" featuring 2 Chainz - B.o.B gets ratchet with some help from DJ Mustard and 2 Chainz on this hit single, which has already been heating up the charts for weeks. The moral of this one: Don't leave your girl alone around Bobby Ray or Mr. Chainz. (Photo: Christopher Polk/Getty Images for Vh1)

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The Evolution of B.o.B - Today Atlanta rapper-singer-guitarist, B.o.B. is coming through!  Click on to follow B.o.B's journey to the top, one benchmark at a time and get ready for a special interview and his new album release Underground Luxury tonight at 6P/5C!(Photo: Christopher Polk/Getty Images for VH1)

The Evolution of B.o.B - B.o.B was born Bobby Ray Simmons Jr. on November 15, 1988, in Winston-Salem, North Carolina. (Photo: Ray Tamarra/Getty Images)

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Born & Raised - B.o.B was born Bobby Ray Simmons Jr. on November 15, 1988, in Winston-Salem, North Carolina.(Photo: Ray Tamarra/Getty Images)

The Evolution of B.o.B - B.o.B took a shine to music early, beginning with playing trumpet while in elementary school. That musicality has carried over into his hip hop career ? he's known for singing and strumming guitar as well as rapping. (Photo: Kristian Dowling/PictureGroup)

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Multiinstrumentalist - B.o.B took a shine to music early, beginning with playing trumpet while in elementary school. That musicality has carried over into his hip hop career — he's known for singing and strumming guitar as well as rapping.(Photo: Kristian Dowling/PictureGroup)

The Evolution of B.o.B - After honing his craft at open mics and nightclubs, B.o.B signed a joint deal with producer Jim Jonsin's Rebel Rock Entertainment, T.I.'s Grand Hustle and Atlantic Records in 2007.(Photo: Jamie McCarthy/Getty Images for AXE)

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Hard Work Pays Off - After honing his craft at open mics and nightclubs, B.o.B signed a joint deal with producer Jim Jonsin's Rebel Rock Entertainment, T.I.'s Grand Hustle and Atlantic Records in 2007.(Photo: Jamie McCarthy/Getty Images for AXE)

The Evolution of B.o.B - Bobby Ray met his first mainstream success in 2008 with his sing-songy single "I'll Be in the Sky" and the accompanying video.(Photo: Courtesy Atlantic Records)

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Touch The Sky - Bobby Ray met his first mainstream success in 2008 with his sing-songy single "I'll Be in the Sky" and the accompanying video.(Photo: Courtesy Atlantic Records)

The Evolution of B.o.B - B.o.B. upped his buzz after signing his deal by unleashing a tidal wave of mixtapes and EPs, including 2009's B.o.B vs. Bobby Ray.(Photo: Courtesy Atlantic Records)

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The Real B.o.B. - B.o.B. upped his buzz after signing his deal by unleashing a tidal wave of mixtapes and EPs, including 2009's B.o.B vs. Bobby Ray.(Photo: Courtesy Atlantic Records)

The Evolution of B.o.B - In 2009, B.o.B graced the cover of XXL magazine's annual Freshmen issue, which features hip hop's most promising new talent.(Photo: Courtesy XXL Magazine)

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The Freshman - In 2009, B.o.B graced the cover of XXL magazine's annual Freshmen issue, which features hip hop's most promising new talent.(Photo: Courtesy XXL Magazine)

The Evolution of B.o.B - Talk about a quick start. The pop-rap hybrid "Nothin' on You," the first single from his debut album which featured hitmaking singer-songwriter Bruno Mars, hit No. 1 in the U.S.(Photo: Courtesy Atlantic Records)

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Nothin' On You - Talk about a quick start. The pop-rap hybrid "Nothin' on You," the first single from his debut album which featured hitmaking singer-songwriter Bruno Mars, hit No. 1 in the U.S.(Photo: Courtesy Atlantic Records)

The Evolution of B.o.B - The song pushed B.o.B's debut album, The Adventures of Bobby Ray, to a No. 1 debut on Billboard. B.o.B had arrived.(Photo: Courtesy Atlantic Records)

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No. 1 Baby - The song pushed B.o.B's debut album, The Adventures of Bobby Ray, to a No. 1 debut on Billboard. B.o.B had arrived.(Photo: Courtesy Atlantic Records)

The Evolution of B.o.B - In one of the weirder recent rap beefs, B.o.B bumped heads with Tyler, the Creator. The Odd Future leader had randomly called out B.o.B on his 2010 hit "Yonkers," rapping, "I'll crash that fuckin' 'Airplane' that that f----t n---a B.o.B is in." B.o.B. responded with subliminal but powerful shots on the leaked track "No Future," which even had Tyler himself tweeting praise.(Photos: EPA/STEVE C. MITCHELL/Landov; Chung Sung-Jun/Getty Images)

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Kill The Beef - In one of the weirder recent rap beefs, B.o.B bumped heads with Tyler, the Creator. The Odd Future leader had randomly called out B.o.B on his 2010 hit "Yonkers," rapping, "I'll crash that fuckin' 'Airplane' that that f----t n---a B.o.B is in." B.o.B. responded with subliminal but powerful shots on the leaked track "No Future," which even had Tyler himself tweeting praise.(Photos: EPA/STEVE C. MITCHELL/Landov; Chung Sung-Jun/Getty Images)

The Evolution of B.o.B. - After a star-making performance with Bruno Mars and Janelle Mon?e at the 2011 Grammys, B.o.B dropped his eighth (!) mixtape E.P.I.C. (Every Play Is Crucial) late last year to ramp up the hype for his second album. (Photo: Brad Barket/PictureGroup)

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True Talent - After a star-making performance with Bruno Mars and Janelle Monáe at the 2011 Grammys, B.o.B dropped his eighth (!) mixtape E.P.I.C. (Every Play Is Crucial) late last year to ramp up the hype for his second album.(Photo: Brad Barket/PictureGroup)

The Evolution of B.o.B - The first single from B.o.B's new album, Strange Clouds, is the title track featuring Lil Wayne. With amazing rhymes and a dubstep-influenced beat, the song is a decidedly harder direction for Bobby Ray.(Photos: Chris Blumenshine/PictureGroup; Mark Davis/Getty Images for Caesars Entertainment)

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Weezy and Bobby Ray - The first single from B.o.B's new album, Strange Clouds, is the title track featuring Lil Wayne. With amazing rhymes and a dubstep-influenced beat, the song is a decidedly harder direction for Bobby Ray.(Photos: Chris Blumenshine/PictureGroup; Mark Davis/Getty Images for Caesars Entertainment)

The Evolution of B.o.B - B.o.B looks to dominate the charts yet again when Strange Clouds, which features appearances from Nicki Minaj, Chris Brown, Taylor Swift, the aforementioned Weezy and many others. But Bob has more up his sleeve in the near future, including a rumored collaborative album with his mentor T.I., The Man and the Martian.   (Photo: Chris Blumenshine/PictureGroup)

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Domination - B.o.B dominated the charts yet again when Strange Clouds, which features appearances from Nicki Minaj, Chris Brown, Taylor Swift, the aforementioned Weezy and many others. But Bobby has more up his sleeve in the near future, including the release of Underground Luxury! Don't miss B.o.B. tonight on 106! (Photo: Chris Blumenshine/PictureGroup)