Jay Z is Top Five, Dead or Alive by default not only because is he a gifted lyricist, incomparable hitmaker, and New York hip-hop ambassador. No, Jay Z’s place in the canon comes from the fact that Shawn Carter embodies a lifestyle. His body of work and biography — the real-life story of a doomed drug dealer who becomes a legitimate businessman and, later, a business, man — has helped shaped an entire culture’s weltanschauung. But back in the mid-’90s, Jay Z was just another guy trying to get signed.
Hov had already proven himself before his debut, Reasonable Doubt, dropped on June 25, 1996: His demos were classics, he spit rhymes at ridiculous speeds, and he had a co-sign from legendary OG Big Daddy Kane. Still, DJ Clark Kent, formerly an A&R at Atlantic, couldn’t convince executives that the artist then known as Jaÿ-Z was a bankable star. He saw what Jigga was capable of during those pre-Doubt days and his frustration boiled: “For a while I was like, ‘F**k all A&Rs,’ because I was like, ‘I tried to show you this s**t.’ Like, ‘What makes you not see this?’”
After a deal with Payday Records fell through, Jay Z pooled his money with fellow entrepreneurs Dame Dash and Kareem “Biggs” Burke to form Roc-a-Fella records and finally release his hustler’s bible, Reasonable Doubt, which went on to become a new standard for East Coast street rap. A skillfully woven tale of crime and glamour, the album remains a grand accomplishment, especially considering its relatively small-scale ambitions: Jay Z and his talented team just wanted to prove they were the best in the game. They weren’t planning to continuously shift the culture for two decades, or lay the groundwork for a hip-hop empire. They weren’t even planning to release a follow-up.