Jay-Z produced some big hits in the '90s, but his evolution in the 2000s not only redefined his own artistry, but the hip-hop realm altogether. The term "businessman" is used toward Shawn Carter almost as frequently as "rapper," as he's launched a successful clothing endeavor, expanded his Roc-a-Fella dynasty in the early 2000s, then rolling it over into Def Jam, of which he was CEO for a few years. He signed big-name artists like Rihanna and yielded some of the decades' biggest hits, like "Crazy in Love" with then-girlfriend, now-wife Beyonce.

Photo: Jay-Z in 2001.