What does his name mean?
B.o.B, born Bobby Ray Simmons, takes his rap name from the 2000 Outkast single, "B.O.B (Bombs Over Baghdad)." That's more than appropriate given that song's genre-crossing style and B.o.B's own tendency to inject the sounds of rock, pop, and R&B into his Atlanta hip-hop.

Do the Outkast comparisons go further than just his name?
Yes. When B.O.B was still a buzzing mixtape rapper, he was frequently compared to Outkast's Andre 3000 for his lyrical dexterity, his emotional content and his occasional criticisms of hip-hop. The 2009 song “Generation Lost” is an example of B.o.B at his most Andre 3000-like. There's also “I'll Be In The Sky” off B.o.B Presents: The Adventures of Bobby Ray and his hook on T.I.'s “On Top of the World,” both of which suggest an Andre 3000-like fusion of rapping and singing.

Do B.o.B's mixtapes sound different than B.o.B Presents: The Adventures of Bobby Ray?
Yes and no. Certainly, there is far less star power and pop shine to his mixtape work, but B.o.B has always dabbled in fusion and experimentation. “Lonely People," from the mixtape Who The F#@k is B.o.B, sampled the Beatles' “Eleanor Rigby” and for a little while in 2009, he referred to himself as “Bobby Ray” and was performing with a live band and playing guitar.

Can you tell me more about the Bobby Ray name change?
For a short time, B.o.B became Bobby Ray, a guitar playing, folk-rap troubadour. It seemed to dovetail with a performance at the 2009 South by Southwest festival in which B.o.B, er, Bobby Ray played with a live band called the Eastsiders. He even teased the name change to hip-hop website Sohh the week of SXSW. Bobby Ray and the Eastsiders weren't so good, but they weren't Lil Wayne Rebirth bad either.

Is B.o.B a rapper or a singer?
A fair, if persnickety, question. If you need to make a choice, he's a rapper. B.o.B hands the sung hooks over to others, like Hayley Williams on “Airplanes” or Bruno Mars on “Nothin' On You.” Listen to B.o.B Presents: The Adventures Of Bobby Ray and between the soaring hooks and production from hitmakers like Dr. Luke and Alex Da Kid, you'll hear some of the most attentive and lyric-oriented rap that's been on the radio in quite some time.

My snooty hip-hop friends say that B.o.B sold out? True?
Some would agree, given the aforementioned ties to gritty Southern hip-hop, but it's not that simple. B.o.B is 22 years old and very much from the internet and iPod generation, so these perceptions of borders between genres and style are non-existent to him. B.o.B produced five of B.o.B Presents: Adventures Of Bobby Ray's tracks, including one of the singles, "Don't Let Me Fall," and there's not exactly a dearth of rapping on here, it just isn't only about rapping. Given the star power on the album, it's easy to suggest a grab for the charts, but this has always been part of B.o.B's music.

Did B.o.B retire at some point?
There was a period of time in which the transition from hip-hop's next big thing to pop-rap superstar seemed almost too much for B.o.B. The “Bobby Ray” identity crisis was one part of this, but no longer having the luxury to release his  music to the internet for free via mixtapes led to an existential dilemma. “It does get frustrating,” B.o.B told MTV, “trying to be free as possible but at the same time working with people.” Ultimately he didn't retire and B.o.B Presents: The Adventures Of Bobby Ray proved his ability to transition from hype to the real thing.