How Jay-Z Met H.P.: Blame Hip Hop Branding Wizard Steve Stoute

Former record exec Steve Stoute and the case of the secret chewing-gum jingle.

Mr. Stoute, 41, was born in Queens Village, the son of Trinidadian immigrants. His father was a marine engineer; mom was a nurse. He spent his formative years grinding away at after-school jobs—he shoveled snow, erected tents at flea markets, delivered the New York Daily News and Newsday, sung Christmas carols and hawked fire extinguishers—but dreamed of being a professional football player. He was a starting running back at Holy Cross High School in Brooklyn, but began hunting for a backup plan after separating his shoulder. His father suggested becoming an auto mechanic. Mr. Stoute remembers his father’s reasoning: “It’s a craft that they can’t take away from you,” he said.

Instead, he bounced around five colleges and began working in real estate, signing homeowners up for mortgages—this was back in the early 1990s, well before the boom and eventual bust. He then left the mortgage market after realizing he could earn more in the music industry. It wasn’t about his love for the music, he said, unabashedly. “No, it was opportunity,” he said. “[Hip-hop] was blowing up. In ’91, ’92, the arrow was pointing in one direction.”

Through mutual acquaintances, Mr. Stoute hooked up with comedy rappers Kid N’ Play and quickly became the duo’s road manager. But his big break occurred in the mid-1990s, when he started managing the rapper Nas. Under Mr. Stoute’s guidance, the Queensbridge emcee adapted a more commercial, radio-friendly sound. The strategy worked. His 1996 album It Was Written was certified double-platinum, but finding the right balance between art and commerce proved challenging. “Managing Nas taught me a lot about respecting artists,” Mr. Stoute said. “You got a crash course in that because you were dealing with a guy who, money didn’t matter to him. Nor did success. He could have been in The Cider House Rules—he didn’t want to do it.” Mr. Stoute shook his head. “Brands were calling—he didn’t show up for some shoots. Nas wrote songs on the Men in Black soundtrack. He could have wrote the whole album for Will Smith but he didn’t want to show up to the studio to write records for Will Smith.”

Men in Black was a huge hit. The movie grossed $587 million worldwide and the soundtrack, which Mr. Stoute executive produced, was certified triple platinum. He was more impressed, however, by the success of a product placement—sales of Ray-Ban sunglasses shot up 500 percent after being promoted in the film.