Bad boy or pop pin-up? "Why not both?" appears to be Sean Kingston's answer to the dilemma of which role he's striving to fit into in his blossoming hip-hop career. Born in Miami, raised in Kingston, Jamaica, his accent lends his rhymes an exotic touch that's alluring to listeners. His story is a gritty, rough and tumble tale of survival that ends with a crafty hustler climbing his way up the pop charts.

Kingston was raised in a troubled home, with a mother and sister who were arrested and eventually put in jail. At that time, young Sean had to fend for himself, living out of a car. He would later write a song entitled "Dry Your Eyes," an ode to his mother and sister telling them to wipe away the tears and know he's waiting for them on the outside.

Naturally, while his mother and sister were getting into trouble, Sean was developing his own bad streak. He was arrested at age 11 for breaking and entering, and at 15 he experienced the arrest of his mother and sister. By the time he was a late teen, he didn't have many options open to him outside of hustling. Fortunately, his parents had been active rap fans, and he had a steady musical diet of Ice Cube and Rakim growing up. He created a profile on MySpace and endlessly pestered producer J.R. Rotem. Rotem finally gave in, meeting with Sean and deciding he had potential.

At age 16, Sean scored a hit single with "Colors 2007." A self-titled full-length album soon followed, earning Sean Kingston the fame he had worked for. But while his first few singles painted him as a reggae-loving rudeboy and hustler, his pop streak has grown, and he proved successful in recording romantic ballads.