Hugh Hefner — Troubled Playboy Icon Dead At 91

Hugh Hefner has died of natural causes at the age of 91 in his beloved Playboy Mansion — plagued by scandals in his tragic final years!

Mourners gathered outside the gates of Hefner's notorious headquarters for his girlie empire, where the magazine publisher was allowed to live after the rotting property had already been sold to a real-estate investor. His son Cooper, already serving as the chief creative officer of Playboy Enterprises, said: 'He will be greatly missed by many, including his wife Crystal, my sister Christie and my brothers David and Marston, and all of us at Playboy Enterprises.'

Cooper also praised his father as a "leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom." But in a tragic twist, Hefner also spent his final embroiled in a Playboy Mansion rape case filed against his longtime pal Bill Cosby.

Hefner also had to struggle with Cooper taking over the Playboy empire after his son Marston — originally groomed as Hef's successor — was arrested in 2011 for domestic assault in a case involving former Playmate of the Year Claire Sinclair. He pleaded no contest to assault charges, and a vandalism charge was dropped after he completed a domestic violence program. Marston (with Claire at far left, and Cooper at right) now teaches English in Japan.

Mourning fans gathered outside the gates of the Playboy Mansion, with several playing Hefner's favorite game of backgammon in tribute. "He thought he'd live to be 100," said one Playboy Enterprises veteran, "but even Hef didn't think his final years would be this scandalous!"