With a Rolex Masterpiece on his wrist and superstar wife Beyoncé by his side, Jay-Z is the king of the modern music world as a hip-hop star and powerful executive. At the turn of the century in 1999, Jay-Z was spending the summer in style in the Hamptons. When New York Magazine wrote a cover story about the rapper in the heart of the American Waspland, Jay-Z was proud to wear his brand new Rolex Masterpiece on his wrist. When asked about the watch, Jay-Z smiled with a secret pride. “It’s a Masterpiece Rolex,” Jay-Z said demurely, allowing an inspection of the diamond-studded watch twinkling on his wrist. “I was, like, the first one in the country with it. I try to stay on top of things. It’s a little hobby, know what I’m saying? I read the Robb Report, the duPont Registry, things like that. I tend not toward expensive — more toward exclusive.” Goose Creek, the Wainscott mansion Jay-Z settled on for a two-weekend rental in July, was not exactly the Maidstone Club, the heart of the Hamptons old money power scene: “It’s the Hilton of the Hamptons,” scoffed a society matron back in the day. “I felt like a little kid in a big haunted house in there,” said Jay-Z, laughing. The $20 million, 30,000-square-foot, Italianate stucco house sits on eight-and-a-half acres of land and is equipped with an indoor-outdoor pool, tennis courts, a spa, a 120-seat screening room, and a canoe and rowboat to tool around Georgica Pond (which is shared by Steven Spielberg, among other players). Former renters include Madonna, Warren Beatty, and Kevin Costner. Meg Ryan and Ed Burns were neighbors of Jay-Z that summer, and Sandra Bullock was next door in the estate’s smaller farmhouse, known as Main Street. However, Jay-Z was the only human being in the Hamptons that summer with a brand new Rolex Masterpiece on his wrist, reflecting his amazing success.

Embodying the rags-to-riches rap dream, Jay-Z pulled himself up by his bootstraps as a youth to eventually become the reigning rapper of New York City and, in turn, a major-label. In the wake of his 1996 debut, Reasonable Doubt, Jay-Z’s albums sold millions upon millions with each release, and his endless parade of hits made him omnipresent on urban radio and video television. In addition, Jay-Z has been loyal to Rolex watches throughout his career, wearing a stainless steel Rolex Day-Date on the cover of In My Lifetime, Volume I. The hip-hop artist retains a strongly devoted fan base and challenges whatever rivals attempted to oust him from atop the rap game, sparing most memorably with Nas. Jay-Z and his Roc-a-Fella associates greatly influenced the industry and established many of the trends that pervaded during the late ’90s and early 2000s. He collaborated with the hottest rappers in the industry, everyone from East Coast contemporaries like the Notorious B.I.G. (”Brooklyn’s Finest”) and DMX (”Cash, Money, Hoes”), to the best rappers from the South like Ludacris and the West Coast like Snoop Dogg. Later, Jay-Z accepted an offer to assume the role of president at Def Jam Records. The seminal rap label was struggling and needed someone to guide it through a rocky transitional phase. Jay-Z embraced the challenge and took over the company began Russell Simmons and Rick Rubin roughly 20 years earlier. Considerable fanfare met the presidential inauguration, as Jay-Z became one of the few African-American major-label executives in the business, and he became one of the few rappers to transition into that side of the business. Numerous rappers owned or operated their own boutique labels, but none had ever risen to such major-label heights. In addition, the rapper-turned-president did not take his job lightly, either, at least judging by his initial year in office. Within months of assuming his position, he fostered a string of newfound, including Rihanna and Young Jeezy. In 2005 Jay-Z came out of retirement for the I Declare War concert in New York City. The ambitious show featured a parade of high-profile guest stars, including P. Diddy and Kanye West. With this longstanding beef squashed, Jay-Z announced he was coming out of retirement for good. He made it official when Kingdom Come hit the shelves in late 2006. Since then, Jay-Z has rocked the music world with a Rolex Masterpiece on his wrist as both a hip-hop star and a visionary music executive.

Tags: Beyoncé, Georgica Pond, Jay-z, jayz, Kanye West, P. Diddy

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