"When you look at what's happening, the record business is purging itself," Jay continues. "Def Jam released 57 albums one year. Are there 57 good artists in the world, let alone on one label? If you have 57 artists and four of them break, that's bad business. What a terrible model. I told them, 'How about this idea — instead of spending $300 million to break four acts, why don't you guys give me a credit line, and I'll just do things. I won't make music. I'll go buy some headphones, or buy a clothing line, just be part of the culture.' But the money scared them off, because they're not used to thinking in that way."
Despite the impossibility of changing an ossified record-business model overnight, Jay did manage a smooth transition into the world of the corporate boardroom, which makes one wonder if the experience changed his feelings about race in America. Jay smiles diplomatically and says, "No, it didn't." He mentions Chris Rock's great stand-up bit about Alpine, New Jersey, the wealthy neighborhood where Jay used to live: "In my neighborhood, there are four black people," Rock said. "Hundreds of houses, four black people. Who are these black people? Well, there's me, Mary J. Blige, Jay-Z and Eddie Murphy. . . . Mary J. Blige, one of the greatest R&B singers to ever walk the Earth. Jay-Z, one of the greatest rappers to ever live. Eddie Murphy, one of the funniest actors to ever, ever do it. Do you know what the white man who lives next door to me does for a living? He's a fucking dentist!" Jay chuckles and, paraphrasing Rock, says, "'He didn't discover teeth!'" Twirling a forkful of pasta, Jay continues, "It's changing slowly. But it's not an equal thing. I'm here because of my talent. You still have to do extraordinary things."
As we exit Jay's office building, passing under the stern glare of a bust of former Israeli prime minister Golda Meir, an unsmiling, shaved-headed bodyguard appears and opens the door of a black Cadillac Escalade parked on Broadway. The rear seats have been tilted so far back, it almost feels as if we're lying next to each other on beach chairs. Jay, not entirely surprisingly, turns out to be a backseat navigator. On an earlier ride, he began to give the chauffeur (who calls him "boss") his own directions to a photo studio. "Just keep going until you see the Richard Meier building," he commanded. The driver stared blankly in the rearview mirror. "The big glass building on the left," Jay said. "The architect is Richard Meier."
Tonight, as we drive the 12 blocks to the Four Seasons, Jay says, "You're going to meet a guy named François who's been a good friend and is the reason I'm doing this." François-Henry Bennahmias is the North American president of Audemars Piguet, the luxury Swiss watch brand; tonight, he's sponsoring a celebrity watch auction to benefit an AIDS charity. The auction is already under way when we're ushered to the front row and seated directly across the aisle from Kelsey Grammer, who beams at Jay's arrival. The rest of the well-heeled crowd also seems starstruck. A rich guy sitting behind us who looks a bit like Mickey Rourke has not silenced his cellphone, which goes off in the middle of the auction, blaring an "Empire State of Mind" ringtone. "Shawn! Shawn! Check it out!" the man brays, leaning forward and holding up his phone to a mortified Jay.
Jay picks up the price list, scans it, then elbows me and points out a limited-edition Lady Millenary Astrologia watch signed by Meryl Streep, with an estimated value of $120,240. "I might bid on this one," he whispers. "They're giving 'em away in this room." But when the lot goes up, the bids hit 70 grand within seconds. Frowning, Jay glances over and says, "This isn't going to work out for me." He ends up not bidding at all.
Jay's watch, a limited-edition Royal Oak Offshore Las Vegas Strip Tourbillon, with an estimated value of $217,800, is the main event. When it's Jay's turn to say a few words, he acknowledges the other celebrities in the audience, including "Chelsea Grammer." Jay's watch ends up as the biggest seller of the evening, going for $220,000. At the afterparty, the babyfaced actor and rapper Nick Cannon approaches Jay in the corner and says, "Man, you said Chelsea Grammer!" Jay says, "Really?!" Cannon, still laughing heartily, says, "I just about fell out of my seat! He rolled with it, though. I looked over and he was just smiling and clapping." Jay laughs, too, sorrowfully shaking his head.
Back in the Escalade, he turns to me and asks, "Did you hear me say Chelsea Grammer?"
"Yeah," I say, "but you said it pretty quickly, so I'm not sure that everyone necessarily caught it."
He frowns and shakes his head, seeming irritated with himself. "Nah. If you heard it, and he heard it, everyone heard it." As the Cadillac maneuvers through the downtown traffic, Jay begins typing a message to someone on his BlackBerry. Without looking up, he asks, "How do you spell 'faux pas'?"
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