In his music, 50 revels in his violent past as a drug dealer.
The presence of guns and violence are not far from many of his music videos.
But for industry watcher, Lucian James from the San Francisco-based Agenda, 50 Cent and his fellow hip-hop stars have been extremely canny.
"What people like 50 Cent have been able to do is to kind of repackage their early lives in a way that is a lot more brand-friendly, so there's an edge that's associated with it, but it's not something that the brands perceive as a real risk to them."
For some big brands, trying to buy cool has failed.
McDonald's, the world's biggest fast food chain, is desperate to keep in with the youth market and saw hip hop as the key to a piece of the action.
Last year, they offered to pay artists to rap about Big Macs.
The deal was cash per airplay for any song featuring a Big Mac.
Not surprisingly, the idea never flew, as not a single band would take up the offer from McDonald's.
DJ Semtex, hip-hop DJ for the BBC's 1Xtra radio station, says artists don't want to be seen to be bought.
"I think the problem with McDonalds is they were too blatant with their aims of what they wanted to do within hip hop.
The way that they came up the scene was like 'yeah, we're going to get into this culture and we're going to exploit and make some money and you're going to buy our food'."
But if companies are desperate to get on with 50 Cent, the same cannot be said for parents, who are upset by the language used in songs like I'm Supposed to Die Tonight, Gunz Come Out, P.I.M.P. and Wanksta.
We spoke to Wendy Payne and Wendy Rose whose daughters Chanice, Charlotte and Emma are huge 50 Cent fans.
"When he says motherf*****, I don't like that at all," says Ms Rose.
"It's not always necessary, the constant swearing," adds Ms Payne. |