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Why Damon Dash Hates Mondays

“As a kid, I always knew he’d do pretty much something,” says Damon’s older brother, Bobby Dash, a longtime employee of Dash’s enterprises. “When we saw Superman, the little nigga was asking questions every two minutes. When he was like 16, 17, and I got into trouble with a crack game, I always called on him to get me out of the jam.”

Dash was in and out of a number of public and, because he was a whiz on standardized tests, private schools (via scholarships from the Boys Club). He went to the Dwight School; Isaac Newton; Manhattan Center; South Kent, a boarding school in Connecticut with a reputation as a magnet school for kids with disciplinary problems (and where he cast himself as an athlete, lettering in football, basketball, and even lacrosse); and, finally, Westside High. “Westside was for everybody that got kicked out of the place you went when you got kicked out of someplace else,” he says. He even managed to get expelled from Westside, for driving his car to school and parking in the principal’s spot. After that, he got his GED.

He was always ambitious, even about goofing off. “It was Damon’s idea to start throwing parties, and we rented out the Cotton Club and started charging money,” says Steve Mack, a childhood friend who works for Dash’s record label. Word spread about the parties—Dash credits their success largely to a standing offer to give a free bottle of Moët & Chandon to the first 100 ladies in the door each week. Rappers began showing up, pro athletes with road games in New York, Mike Tyson.

“It was going so well, I said, ‘We should do a record company and a clothing line,’ ” Dash says. The only problem was that he didn’t make any music—didn’t rap, didn’t write rhymes, didn’t know how to produce a record. He didn’t even have a particular musical sensibility or, at that point, a very good ear. He did, however, believe that he understood how to put his Harlem experience in the appropriate consumer context. In 1990, his cousin Darien Dash brought him to a party for Heavy D. “I looked around and saw that all the people there were older than me, they had money, and they looked like they were trying to be like me and my crew,” he says. “I knew I could make money from this.”

The Dash cousins began to manage an act, the Future Sound, and got the group a record deal with Atlantic. The executive who signed them was Clark Kent—real name Rodolfo Franklin—who moonlighted as a D.J. and had his ear close to the ground. In 1994, Kent told Dash he had to meet a former drug dealer from Brooklyn who was trying to get a career as a rapper off the ground.

“I’d never heard anybody rap so fast,” Dash recalls of the rapper, whose name was Shawn Carter and who came to be known to the world as Jay-Z. In addition, his songs were full of clever, metaphor-heavy rhymes (“I’ve got extensive hos with expensive clothes / I sip fine wine and spit vintage flows”). Dash put up money for him to record a bunch of songs and, when a record deal was not forthcoming, began pressing the discs himself and selling them out of his car, and Roc-A-Fella Records was born. To try to get on the radio, Dash shot a video for Jay-Z’s song “In My Lifetime” for $16,000, on 16-mm. film, borrowing a friend’s boat in St. Thomas to film a scene of what looked like a playboy’s living the high life.

Jay-Z’s first album, Reasonable Doubt, was released in 1996 to critical huzzahs. The hip-hop scene was dominated by the funk-based sound of West Coast gangsta rap—Dr. Dre, Snoop Dogg, and Tupac Shakur—and its violent dispatches from the black underclass. Jay-Z’s sound was more soulful and his wordplay more dense (about his later dominance of his competitors, he has rapped, “Fucks too lazy to make up shit they crazy / They don’t paint pictures, they just trace me”).

Dash was savvy from the beginning, insisting on equity at most every turn—embodying hip-hop’s break from the work-for-hire arrangement that had historically plagued black recording artists. When he and Jay-Z were offered distribution deals with big record companies, Dash held out for a co-ownership with Def Jam.

Although Jay-Z had already spent years searching in vain for a record deal, Dash says he was drawn to him from the outset. “Everybody thought he was too old; they didn’t like the way he dressed: like a Harlem dude. He wore Nike Airs, which everybody called uptowns.” The class distinctions were lost on nobody. “The Brooklyn cats who were more dominant were known for doing things like gold teeth, much more ghetto,” and they viewed Harlem’s aesthetic as soft. But Dash saw in Jay-Z a sort of uptown swagger. “I was shocked. Here was a guy with the same aspirations that I had. We wanted to be known for making money. All we talked about was making money and how to spend it, what the best of everything was and how bad we wanted it.”