Planes, Trains, And Automobiles…

Pictured here next to his private Playboy jet, Hugh Hefner is in a familiar position (you guessed it), alongside a cast and crew of babes and beauties. In an always dapper suit and tie, the Playboy entrepreneur casts a gaze that personifies his lifelong act in one snapshot, surrounded by his “employees”. It’s hard to imagine anyone playing Hugh Hefner’s role any better than the way he does. Pictured once more with his signature pipe, Hugh Hefner completely surrounds the pinnacle role of his time; his ability to “Wow” the women, while also remain ambivalent towards their affection. With his arm hooked around his “main” bunny, and his come-and-get-me smile that can be seen from a mile away, Hefner continues to knock us off our feet.