Frank Sinatra Is One of Diddy's 'Imaginary Friends'

The hip hop impresario, who recently had surgery to repair his right rotator cuff, takes on the legendary crooner in a new ad

By Christina Tapper

Published on October 10, 2008 12:25PM EDT

He may have his hands full as a rapper, actor, and CEO, but Diddy is never one to be all business and no pleasure. In his latest TV ad, he manages to cover both simultaneously by paying homage to Frank Sinatra.

But recent days haven’t been a total party. Last week, Diddy had surgery to repair his right rotator cuff.

Still, injury or no injury, the hip hop mogul still knows how to get down.

“There’s nights in Vegas when I have my Frankie baby with me. That’s right, Frank Sinatra is with me. Call me crazy. I’m not afraid to say I have imaginary friends,” Diddy quips. “And Frank is one of them.”

A tuxedoed Diddy hosts a swanky house party in Ciroc Vodka’s newest commercial that evokes Sinatra’s era. It was shot in black and white at one of Sinatra’s California homes and features the late singer’s classic, “Come Fly With Me.”

“He’s always influenced me and naturally inspired me,” Diddy, who announced his partnership with the vodka brand last year, tells PEOPLE. “So this was me honoring Sinatra, the Rat Pack, and the style and sophistication of that time.”

Although generations apart, Diddy, 38, says he has a lot in common with Ol’ Blue Eyes, like entertaining.

“I love showing people a good time, throwing parties and seeing people have fun. That’s me,” says Diddy. “And Frank was the same. He loved entertaining.”

The soiree that’s seen in the Ciroc commercial actually lasted six hours – and got a little wild.

“Somebody got naked and got into the pool. Actually two people did. And one of them was me,” Diddy admits. “We have that footage locked away and in a safe. I always keep cameras rolling. You never know what may happen.”

Skinny-dipping aside, the hip hop mogul is said to favor Sinatra so much so that, according to Diddy, rapper Chuck D of Public Enemy dubbed him the “Black Sinatra” a few years ago. He doesn’t take the title lightly.

“His swagger and the confidence he exuded – I have so much respect for Sinatra so it was a shining moment in my life for someone to call me that, Diddy says.

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