A hip-hop icon who started off as an underground battle rapper in Detroit. Marshall “Eminem” Mathers has developed a career full of contradictions; wild swings; and some of the most noteworthy hip-hop of the past decade. Produced and co-signed by Dr. Dre, Em had an unprecedented run of success from 1999 up through 2003, releasing three well-reviewed, multi-platinum albums, stealing the show on countless collaborations, and even starring in a hit movie. However, it all came crashing down around 2004, when a string of problems ranging from drug dependence to depression to the tragic death of best friend Deshaun “Proof” Holton in 2006 led to a long hiatus from music and a string of what were, by his own admission, sub-par albums.

When you look at Jay Z, what do you see? When 50 Cent looks at Hov, he sees an MC who “capitalized on people” better than he did. What does that mean? Let Fif provide some context. “I think back to when I was with someone and that person could have been the person I was going to be with for the rest of my life but I didn’t have the references yet to know there was something special there,” he told The Big Issue. “It’s like the clarity I got about my grandmother after she was gone. Some people have been better at that than me. If I look at Jay Z, I’d point out he capitalized on people better than I did.”