Sean Combs: Playboy Interview

Sean Combs circles a coffee table in black boxers and a white wifebeater. He has stripped to his underwear inside what is likely the biggest walk-in closet in New York City. Surrounded by racks of clothes, footwear, eyewear and jewelry, the Harlem businessman turned rapper turned clothing designer turned actor turned television producer turned restaurateur turned vodka and fragrance endorser has transformed a Times Square two-bedroom apartment into a changing room. Combs's favorite kind of statement is overstatement.

Outside of finding a proper outfit, the performer known as Diddy has no worries. From playing Walter Lee Younger in A Raisin in the Sun on Broadway to releasing his sixth solo album, the techno music experiment Last Train to Paris, he likes to aim for the improbable. He’s meticulous but undaunted by failure.

Diddy believes only in extremes. He treats each day as if it were a party in Ibiza because he doesn’t know when God will take his life. Although he has been around murder since the age of three—in 1972 his father was killed while parked on Central Park West, and in 1997 Combs's best friend, rap star Notorious B.I.G., was fatally shot after leaving an L.A. party thrown by Vibe magazine—he doesn’t fear death. “One time I was on a plane that I felt was going to crash," Combs says, “and a calm came over me.”

 

Born in 1969, Sean John Combs grew up in Harlem’s Esplanade Gardens. The neighborhood was middle class, but the kid had a bigger vision. His family moved to Mount Vernon, New York after his mother, Janice, employed by United Cerebral Palsy, was forced to relocate for work. But the suburbs couldn’t erase the Harlem energy in his DNA. He flipped paper routes for profit as a child and made money throwing parties while enrolled at Howard University. After he was hired as a record-company intern, he quickly proved his ear for hit songs—and other products. In 1994 he started Bad Boy Records, his own label, and five years later he launched Sean John, his own clothing line. He wasn’t even 30.

Combs has five children with three different ex-girlfriends, including Kimberly Porter, but he’s better known for the romance with Jennifer Lopez that lit up tabloids for two and a half years. He has been in the headlines for acts both impetuous and admirable: a felony arrest for gun possession at a Manhattan nightclub, the 1999 assault of a fellow music executive, the $1 million he raised for inner-city education while running a marathon in 2003. That year Fortune named him America’s number-one entrepreneur under 40. In 2009 Forbes estimated his annual income at $30 million.

Playboy sent Vibe editor in chief Jermaine Hall, who has been on land, sea and air with Combs to ask the questions Combs usually dodges. “Puffy tricks you into believing he’s giving you the holy-grail scoop,” says Hall, who has interviewed him twice before. “It’s his charm, his hustle. But when he called me asking if I was getting everything I needed, I knew he was in a different space. We met three times: ‘I want to make this interview special, make this epic,’ he told me. The man with the notorious ego was cheerful and engaging, but behind the mogul who throws decadent birthday parties at Cipriani and rides Jet Skis in bespoke suits, there was a dark character who picked two themes for our discussions: death and love. He’s more terrified of the latter because he hasn’t gotten it right.”