Pitbull the pop star was born that year. Out went the street snarl and crunk-meets-reggaeton thump that powered his early success; in came three-piece suits, four-on-the-floor beats and party anthems that make the Black Eyed Peas sound depressed. "He started to produce these mass-appeal hits that stations all over the country could play," says Sharon Dastur, program director at New York's Z100 radio.
Pitbull's career reboot kicked off with 2009's clubby "I Know You Want Me (Calle Ocho)," which sold 2.7 million downloads and reached Number Two on Billboard's Hot 100. Since then, he's churned out six more Top 20 singles – including last year's Number One smash, "Give Me Everything" – and has guested on major hits by Usher, Jennifer Lopez and Enrique Iglesias. "I'm never worried about overexposing myself," he says. "That shit's for the birds, man. They want new shit all the fucking time."
As part of his reinvention, Pitbull has gone fully, unapologetically corporate – inking lucrative endorsement deals with Bud Light, Kodak, Dr Pepper and Zumba Fitness, as well as securing equity stakes in companies that make vodka, dissolvable energy strips and fast food. "To establish myself as a brand," he says, "I had to do deals with big brands."
He dreams of making music a side hustle to a larger marketing and consulting operation by the time he's 35. Even the luxury aircraft currently carrying us to his next show is part of the overall strategy. "There's no better place to do business than in here, 'cause you can't go no-fucking-where," he says after we reach cruising altitude. "If I got you for four or five hours, I'm-a have that deal cut by the time I land."
Pitbull's arch-capitalist turn has made him an easy target for mockery. Last summer, when he signed on to make an appearance at whichever Walmart won a Facebook contest, a wiseguy blogger marshaled thousands of "likes" for a remote branch in Alaska. "I guess they thought they were going to bully me on the Internet," he says, smiling. "Kodiak was gorgeous."
He does turn down some offers, particularly when he suspects he's being used for his ethnicity. "When I sit in those board meetings, they say 'multicultural' and 'general market,' " he says. "No, motherfucker, multicultural is your general market!"
Pitbull peers out the jet's oval-shape window, sunlight streaming across his face. "I am the American dream," he adds. "Hip-hop gave me an out, and the world is giving me an in. Where do we go from here?" He laughs. "God knows."
After touching down in Salvador, northeastern Brazil's party capital, we head for a local festival, where Pitbull's staff is extremely frustrated to learn that the promoters have failed to supply the video screen required for his blockbuster-grade graphics. One of his managers, Michael Calderon, paces anxiously backstage. "We might be canceling the show," Calderon says with a sigh after ducking out of the star's dressing room.
In the end, Pitbull wins over the crowd without special effects. He opens with his 2011 hit "Hey Baby (Drop It to the Floor)," leaping up and down and barking slick lines even more urgently than he did last night in Rio. He headbangs vigorously to his band's covers of "Seven Nation Army" and "Sweet Child O' Mine" between songs. Before long, young women are climbing on their boyfriends' shoulders to wave their hands frantically and mispronounce his name at the top of their lungs: "PITCHI-BOOL!"
At his hotel a couple of hours after the show, a beautiful brasileira in a tight yellow minidress reclines on the rumpled bed while Pitbull, his engineer and another friend lay down some background vocals for "Hope We Meet Again." "It sounds like a choir of angels," she says dreamily. Pitbull smirks and says, "It sounds like three guys that know how to eat pussy!"
With a glass of white wine in one hand, he uses the other to cue up a few more new songs on his engineer's laptop. "Feel This Moment" has a gale-force Christina Aguilera hook and a sample of A-ha's "Take on Me." "Have Some Fun" is a flirtatious club track featuring British-Irish teen idols the Wanted – "my Fifty Shades of Grey," he announces to general laughter. Next up is a raunchy Akon collaboration, straightforwardly titled "Everybody Fucks."
That last one probably won't be showing up in any Dr Pepper ads. But it's not as if any of this is about to scare off his corporate partners, either. "They're trying to sell a product through my life," Pitbull says. "People believe that I have a fucking good time. Damn right, bitch." He takes another swig of wine. "I have the time of my life."
This story is from the November 22, 2012 issue of Rolling Stone.
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