“Everybody would wear Tommy Hilfiger and Ralph, but they’d wear it a certain way,” Simmons explains (and, by the way, have I heard he’s been with many models?). “You’d look at Ralph’s collection and you’d find one thing you liked.”3
Simmons got tired of watching hip-hop tastes transform companies like Hilfiger into billion-dollar brands, he says. So he launched Phat Farm and packed its catalog with the sort of items that were selling. Not only did he increase the number of street wear items available on the overall market, but he jacked up prices. The Adidas sneakers that Run-D.M.C. rapped about were selling for thirty-eight dollars at the time; Simmons sold similar pairs for eighty dollars. Even Phat Farm T-shirts cost forty bucks.
“You sit there and you see all the areas that you affect,” he says. “People come to you with their ideas about what you’re affecting, about your cultural influence. You may learn to monetize that yourself.”
Phat Farm’s formula wasn’t limited to its tony SoHo flagship. The brand showed up on shelves of independent outlets like Jimmy Jazz, V.I.M., and Dr. Jay’s. These weren’t actually black-owned businesses. (Jimmy Jazz was created by James Khezrie, the son of Syrian immigrants; V.I.M. was launched by the Israeli family behind Jordache jeans; and the head of Dr. Jay’s is named Hymie Betesh—as likely to be a goy as Lyor Cohen. It’s worth noting that none of these companies replied to my requests for comment.) The stores were located in places like Brooklyn and Harlem; in the latter neighborhood, Simmons remembers there being three Jimmy Jazz stores on a single block. That meant a lot, especially during a time when few big names in the fashion world dared venture into low-income neighborhoods.
“We try to give the customer what he can’t get anywhere else in this area: brand names,” explained Brooklyn-born Khezrie—who launched his company in 1988 and within six years had reached $30 million in annual revenue on sixteen stores, fifteen of them in poor precincts—in a 1995 interview with Crain’s.4
This was especially important as Robert Moses–era urban planning moved shopping centers to the suburbs, exacerbating the decline of cities around the country. When inner-city customers went to local establishments to buy Phat Farm and other hip-hop-influenced clothing, that meant more cash flowing through communities with large black populations. Though the chains’ owners hailed from other backgrounds, they generally hired locally and helped keep stretches of urban storefronts occupied.
“That was a meaningful moment in fashion,” says Simmons. “We were sucking a lot of the wind out of the fashion industry.”5
“When I was moving off the streets and tried to envision what winning looked like, it was Russell Simmons,” Jay-Z wrote in his autobiography. “Russell was a star, the one who created the model for the hip-hop mogul that so many people—Andre Harrell, Puffy, even Suge Knight—went on to follow.”6
And so, as Jay-Z began to consider his next steps after aligning Roc-A-Fella with Simmons’s label, he looked to the Def Jam founder for inspiration. During the late 1990s, Jay-Z wore a lot of clothing by the European designer Iceberg; he often donned the brand at concerts, and soon he found his fans doing the same. So Damon Dash arranged a meeting with the company’s brass, hoping to land an endorsement deal. He and Jay-Z demanded millions of dollars and the use of a private jet; the Iceberg executives offered free clothes.
Needless to say, there was no deal, and Jay-Z and Dash decided they would try the do-it-yourself approach. They hauled sewing machines into the Roc-A-Fella offices and hired people to stitch together early Rocawear prototypes. They weren’t anywhere close to building something scalable: shirts took three weeks each to make. Finally they asked Simmons for advice, and he set them up with his partners at Phat Farm, letting them out of exclusive contracts so that they could work for Rocawear, too. “I wasn’t their manager, but they were part of my company,” the Def Jam founder says of Jay-Z and Dash. “A family.”7
Soon Rocawear replaced Iceberg in Jay-Z’s lyrics and on his person, and the fledgling brand became a real business. Jay-Z had discovered what would become one of the central tenets of his business: whenever possible, own the products you rap about; otherwise, you’re just giving someone else free business. With that in mind, he went back to the studio, aiming to keep his album-per-year streak alive, this time no doubt feeling some pressure to match the career-best performance of his latest effort. But instead of continuing to chase a pop-oriented sound, Jay-Z embarked on another pattern that would serve him well down the line. Just when it seemed he’d gone totally mainstream, he tacked back to the gritty beats and subject matter that first catapulted him to stardom (with a couple of Rocawear references thrown in, of course).
On Vol. 3… Life and Times of S. Carter, he fully abandoned Diddy and his glossy production crew, setting the tone by positioning the DJ Premier–produced “So Ghetto” as the first full-length track on the album. In the song, he tells a tale of cruising in his car with a “bougie broad” who asks him to remove his do-rag—so he hangs a U-turn and dumps her back at the club. “I’m so gangsta prissy chicks don’t wanna fuck with me / I’m so gutter, ghetto girls fall in love with me,” he spits in the chorus.8 He even recruited Dr. Dre for a guest appearance on “Watch Me,” further down in the track listing.
Jay-Z wanted his new album to underscore his street credibility in every way possible, and when it leaked weeks before its December 1999 launch date, he took that notion a step too far. During a party at New York’s now-defunct Kit Kat Club, he confronted Lance “Un” Rivera, the producer on Vol. 3, who Jay-Z believed was responsible for bootlegging the album. Jay-Z reportedly rammed a knife into Rivera’s stomach after offering, as the story goes, a line that revealed lingering mafioso fantasies: “You broke my heart.” Jay-Z turned himself in to the police; after a high-profile perp walk, he was charged with felony assault, eventually pleading guilty to a lesser charge and getting away with three years of probation.9
But little doubt remains over what happened that night. “I stabbed Lance Rivera,” Jay-Z told the judge, according to numerous reports. Jay-Z, barely three years removed from street life, hadn’t yet fully shed his former persona. “I was blacking out with anger,” he said of the incident. Still, the episode came with something of a silver lining for Jay-Z—and a valuable lesson about the nature of publicity.10
“The hilarious thing, if any of this can be considered funny,” Jay-Z wrote, “is that the Rocawear bubble coat I was wearing when they paraded me in front of the cameras started flying off the shelves the last three weeks before Christmas.”
By the middle of the following year, the company was closing in on $50 million in annual revenue.11
By the time Jay-Z’s brush with the law boosted his new clothing line in 1999, Diddy’s Sean John brand had already been established for a year.
With the help of his lawyer Kenny Meiselas, Diddy modeled the Sean John deal after his Bad Boy pact, first finding equity partners: the Sinni brothers, who owned a vast real estate and apparel empire. They contributed financing and handled sales and manufacturing. Diddy oversaw the vision and design, once again making sure he had total control over the product as well as over the use of his name and likeness.12
“He never got caught up in, ‘Okay, I have a clothing line, I’ll put my mother in to run it, I’ll put my sister in to be the designer,’” says Meiselas. “He’s always done it in a real professional way with people who are experts and experienced in those businesses.”
Diddy debuted his line at a Las Vegas trade show in 1998; much like Simmons, he was influenced by designers like Tommy Hilfiger and aspired to create clothing for the members of the hip-hop generation. “We wanted to give them fashion that represents them. We wanted to give them extremely multicultural and diverse fashion,” he told the Washington Post. “We brought them fashion-tainment.”13
Diddy’s first hires were Neiman Marcus veteran Jeff Tweedy and Calvin Klein publicist Paul Wilmot; they often joined him at fashion shows, where he’d sit in the front row a
nd observe what generated the most excitement. He announced Sean John’s New York debut at a cocktail party at Bloomingdale’s in 1999, arriving on the scene in a flurry of security guards and television cameras. Sean John revolved around Diddy, from its moniker (his real first and middle names) to its advertising (the Times Square billboards featured Diddy himself).
Far more than Jay-Z or Dr. Dre—or Simmons—Diddy used personal charisma to prop up his business interests. In 1999, for example, Vogue editor Anna Wintour hired photographer Annie Leibovitz to shoot him with Kate Moss on a bridge in Paris. One classic image featured Diddy, clad in a dark overcoat and a white suit, hand on his chin, seemingly evaluating the supermodel—as though she might not be good enough for him. Another captured Moss and Diddy, both robed in fur, stepping out of a pearly Mercedes into a horde of paparazzi.
This sort of publicity not only helped to up Diddy’s glamour quotient; it also helped make him, and Sean John, a more mainstream brand. (“‘Urban’… I would get insulted when they put us into [that] classification,” he said. “They didn’t do that with other designers.”)14 Soon Sean John was taking up shelf space in stores like Macy’s alongside Calvin Klein and Tommy Hilfiger.
For Diddy, it was all quite the juggling act. Meiselas remembers him bouncing between songwriting sessions and recording studios for his Bad Boy artists while his Sean John employees presented the latest clothing designs for his approval. “I was always amazed by just how much he would do at one time,” the lawyer says. “He was just so driven.”15
In 2003, with Sean John grossing some $175 million annually and available in more than two thousand stores, Diddy bought out the Sinni brothers and teamed up with a new partner: billionaire Ron Burkle, who invested $100 million in the company.16 Diddy kept a controlling stake and stayed on as Sean John’s chief; in 2004, he captured the Council of Fashion Designers of America’s Top Menswear Designer of the Year Award, the first time a black person had won.17
Both Diddy and Jay-Z had taken Simmons’s blueprint and expanded it in a way that he couldn’t as a behind-the-scenes mogul. But their debt to the Def Jam founder was clear. Says rapper Too Short: “Without Russell doing Phat Farm, and then giving [Jay-Z] the game for Rocawear, and then giving [Diddy] the game for Sean John, you’re missing two moguls.”18
While Dr. Dre’s most notable contribution to the world of fashion would ultimately be a headphone line that became as much an accessory as a listening device, he did make one ill-fated foray into the clothing business. His mother convinced him to pony up startup funds for a his-and-hers loungewear line called Dre V Denee. (The V stood for her name, Verna; Denee is the middle name of Dre’s sister.) Its target demographic: middle-aged couples who wanted something other than sweatpants to wear around the house. Verna hatched the idea with the best of intentions: she wanted to repay Dre for buying her expensive homes and cars by creating a business that would make her self-sufficient.19
Verna was a talented seamstress, a skill passed down from her Texas sharecropper parents; she’d had some success crafting African-print outfits and selling them to her husband’s coworkers during Black History Month one year. But the Dre V Denee project was doomed from the beginning, from its clunky name to its outdated concept to its cringeworthy slogan: “Sexy appealing but not so revealing.” The clothing line never got farther than a friends-and-family launch party at Verna’s home, which was probably for the best. Dre’s fashion moment would have to wait.
While Jay-Z and Diddy were getting into the clothing world—and out of all sorts of legal trouble—in 1999, Dre forged ahead with more musical masterpieces. He released his somewhat confusingly titled second studio album, 2001, in November. The name didn’t stop the record from achieving a sextuple-platinum certification in its first year. The album offered a rare glimpse into the world of Dr. Dre, who was becoming something of a recluse in his middle age. In an era when top acts like Jay-Z put out a new album every year, Dre had waited seven years for his follow-up.
As always, keenly aware of his own strengths and weaknesses, he focused on producing—and turned to Eminem, Snoop Dogg, and Jay-Z to cowrite songs like the self-affirming ballad “Still D.R.E.” All three rappers tried to pen verses for that track, but Jay-Z conveyed the essence of being the superproducer better than Dre himself with concise summaries (“Still taking my time to perfect the beat / And I still got love for the streets”) and obscure throwbacks (“It’s not a fluke, it’s been tried, I’m the truth / Since ‘Turn Out the Lights’ from the World Class Wreckin’ Cru”).
“He understood what he was writing for. He took and embodied the whole situation as far as writing for Dr. Dre,” Snoop said in 2012. “We all took a shot at it, but we all couldn’t come up with nothing as dope as Jay-Z.”20
In the broader business, though, nobody could top Eminem at the dawn of the new millennium, at least when it came to music sales. The rapper’s second major label effort, the Dre-produced Marshall Mathers LP, dropped in 2000 and earned a rare diamond certification for sales of more than ten million units in the United States, easily better than Jay-Z and Dre’s career bests. Eminem went on to sell thirty-two million albums during the ensuing decade, more than any other artist, dead or alive—two million more than the Beatles during that period, and nearly 60 percent more than number ten Jay-Z.21
During the summer of 2000, Dre and Snoop headlined the Up in Smoke tour, along with Eminem, Ice Cube, and several others. Kevin Morrow, who ran the House of Blues in Los Angeles and organized Eminem’s first show, served as promoter; though many in the industry had been deterred by the violence that had shaken hip-hop a few years earlier, Morrow realized that the genre had crossed back into the mainstream.
“You started to see record sales that were so huge you really knew, ‘Wow, this isn’t a black thing anymore; this is multicultural,’” he recalls. Just as he’d done in the era of N.W.A., Morrow took a professional approach to concert planning, going into “real buildings with real security and real marketing budgets and real sound and lights… We made it safe.”22
Fans responded, and the forty-four-date excursion went on to gross more than $20 million. But what impressed Morrow most of all was the genre’s reach, which extended to cities far beyond the tour’s route. “Every little kid in friggin’ China or anywhere in Asia, or Europe, wanting to wear his baggy pants and the oversize T-shirts and wearing the Air Jordans? I don’t know anyone doing that in country, in blues, in jazz,” he says. “There’s no musical genre anywhere that’s changed the world like hip-hop.”
Dre had emerged as a go-to producer for all manner of artists, including Gwen Stefani, Mary J. Blige, and even sometime rapper Shaquille O’Neal. The NBA Hall of Famer spent time in the studio with Dre, whom he describes—tongue perhaps in cheek—as “the Michael Jordan of hip-hop.” He also affirms the producer’s reputation as a perfectionist. “You go in there and he never messes around,” Shaq says. “And everything has to be nice and crisp.”23
Shaq remembers Dre repeatedly going back over each part of the song they were working on and meticulously tightening up its individual components. Like many of Dre’s creations, though, the song never came out; according to Shaq, the labels involved couldn’t agree on a release date. He remains hopeful, however, that the track will one day make its debut. “I still have it in my archives,” says Shaq. “That shit was banging.”
By 2001, Dre’s new label was worth over $100 million, at least on paper, after Interscope paid him $35 million for a 30 percent stake. Perhaps the best part of the deal: it bound him and Iovine even closer together, strengthening what would become the most lucrative relationship in each of their respective careers.24
Just as Dre and Diddy bolstered their own brands—and bottom lines—by bringing other artists into their respective stables, Jay-Z signed a raft of rappers to Roc-A-Fella in the new millennium. Among them: Memphis Bleek and Beanie Sigel, each of whom would go on to release three gold-certified albums for the label. Jay-Z also must have n
oticed that there were plenty of rappers, including the belligerent Sigel—born in Philadelphia, he called himself the Broad Street Bully—still making careers off aggressive lyrical imagery. Eminem emerged as the most outrageous of the bunch; many of his songs depicted elaborate fantasies of killing himself or others.
The brutal epoch that had taken the lives of Biggie and Tupac was over, but violence lived on as a viable—and profitable—theme. Though Jay-Z’s altercation with Lance Rivera may have helped sell records and Rocawear items, it had nearly cost him his freedom. And so, for his next move, he launched a lyrical offensive that never placed himself or anyone else in real danger, but brought unprecedented attention to his music by challenging Nas to a fight for hip-hop’s crown.
The Queens-bred emcee had been floundering since Illmatic, and he and Jay-Z had been sending low-level snipes at each other for quite some time. So at New York’s 2001 Summer Jam concert, Jay-Z took it to another level with “Takeover,” a song that called out the Nas-affiliated crew Mobb Deep, ending with a shot at his soon-to-be-chief rival: “Ask Nas, he don’t want it with Hov!” (Jay-Z had recently given himself this godly nickname, a shortening of “Jay-Hova.”) Nas responded with a radio freestyle in which he questioned Jay-Z’s drug-dealing résumé.
Jay-Z hit back with the release of his album The Blueprint, which included “Takeover”—and a new verse in which he pilloried Nas, aiming one of his most pointed barbs at the rapper’s fashion exploits. Nas had appeared in ads for designer Karl Kani, prompting Jay-Z to call him a “fag model” (a curious choice for Jay-Z, himself a budding clothing mogul who occasionally appeared in Rocawear ads). In addition to hurling homophobic slurs, Jay-Z also declared Nas’s rap career over, questioned his business acumen, and even alluded to an affair with the mother of Nas’s daughter.
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