He's won multiple awards including 21 Grammys and a Sports Emmy for outstanding music composition/direction/lyrics in recognition of his Super Bowl XLIV opener of his song "Run This Town" featuring singer Rihanna. Jay has sold millions upon millions of records and was one of the pioneers who helped to define urban music in the late 1990s and early 2000s. Start a debate about the best rap artists in history and three names will always appear on the list: Tupac Shakur, the Notorious B.I.G. "You're going to get locked up or you're going to die." "At some point, you have to have an exit strategy, because your window is very small," he said about drug dealing. Though if you think it's tough out here on the charts, it's nothing compared to what Jay saw on the streets. It helped prepare him for the cutthroat music industry, he has said. Things you can get in easily to get out of life." Or if you want to start some sort of barbershop or car wash-those were the businesses back then. "To be in a drug deal, you need to know what you can spend, what you need to re-up. I was a drug dealer," he told Vanity Fair in 2013. The Jigga man has been very open about his past as an illegal pharmaceutical entrepreneur, both rapping about it and discussing it in interviews. man" has worn, all the while building on what he learned in the hood. Here are just some of the many hats the man who once famously rapped "I'm not a businessman, I'm a business.
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