The Evolution of B.o.B

The MC-singer's new LP is the latest step in a long journey.

"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 - It's Mayday for wack rappers everywhere: Today, May 1, B.o.B is dropping his second album, Strange Clouds. The Atlanta rapper-singer-guitarist is looking to best the meteoric success of his 2010 debut, The Adventures of Bobby Ray, which topped the charts in the wake of smash singles like "Airplanes" and "Nothin' on You." B.o.B's stardom only seemed sudden to the unaware — though he's just 23, he's been in the game since 2007. Click on to follow B.o.B's journey to the top, one benchmark at a time.(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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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)

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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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)

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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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)

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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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)

Photo By Photo: Courtesy Atlantic Records

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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 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)

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 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)

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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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)

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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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)

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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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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The Evolution of B.o.B. - 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)

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The Evolution of B.o.B. - 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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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)

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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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)