In 2002, during an era where mainstream Hip-Hop appeared heavily saturated with gangsterism and hustler narratives, a preppy, middle-class, pink Polo shirt-rockin’ producer from the Chicago suburbs shocked the Rap game by signing to Jay-Z’s Roc-A-Fella Records at its pinnacle. While renowned for his distinctive, soulful production, Kanye West had a notoriously hard time being taken seriously as a rapper. Even his future “Big Brother” and longtime collaborator Jay was hesitant to give the artist his big break, worried that ‘Ye wouldn’t fit into the Roc’s roster. “We all grew up street guys who had to do whatever we had to do to get by,” Jay told Time in 2005. “Then there’s Kanye [West], who to my knowledge has never hustled a day in his life. I didn’t see how it could work.”
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