B.o.B

During the 2010s, B.o.B made his name as an endlessly versatile rap artist, able to deliver a blistering, bar-heavy verse, a sweet chorus, or a rock-ready rhyme with equal conviction. Born Bobby Ray Simmons, Jr., in 1988, he started writing music and playing instruments as a child. As a teen, he parlayed his talents and a handful of underground mixtapes into a deal with Jim Jonsin's Rebel Rock label and T.I.'s Grand Hustle roster, both imprints of Atlantic Records. He garnered comparisons to Andre 3000 early in his career: Both emerged from the Atlanta area, flaunted multiple alter egos, and displayed interests that extended beyond hip-hop. B.o.B, however, became a much more familiar mainstream presence. His 2010 debut, B.o.B Presents: The Adventures of Bobby Ray, yielded the Bruno Mars-assisted love ballad "Nothin' On You," the wistful "Airplanes" with Paramore's Hayley Williams, and "Magic," featuring Weezer frontman Rivers Cuomo. Riding high and not finished demonstrating his range, B.o.B also crafted hits with rap superstars like Lil Wayne and pop giants such as Taylor Swift before dropping off 2015's rock-influenced mixtape Psycadelik Thoughtz. He would eventually leave the major-label system altogether to bolster his own indie label, No Genre, self-releasing multiple projects before announcing that 2018's Naga would be his last. But within a year, he dropped off Southmatic, showing once again that he reserves the right to do everything—including retire—on his own terms.