Playboy Enterprises Inc. (PLA) is every adolescent boy's fantasy -- and every shareholder's nightmare. Shares of Hugh Hefner's media empire have plunged more than 66% over the past three years, as revenue from the company's flagship magazine plunged faster than its other properties, including digital media, could make up for it. Even the 2006 purchase of a multimedia empire founded by Jenna Jameson -- arguably the best-known porn star ever -- did not do much good.

Little wonder that the Chicago-based media company is being shopped around. Eccentric British billionaire Richard Branson was the latest rumored potential sugar daddy for Playboy Enterprises, according to a report in Britain's Daily Mail. Branson, who may have planted the story to begin with, later issued a statement denying any interest in Playboy. (This is the same guy recently photographed kite-surfing with a naked model on his back, so the confusion is understandable.)

Maybe Playboy is playing games. The company's interim CEO, Jerome Kern, who replaced Hefner's daughter, Christie at the top, said in February that the company would be "willing to listen" to suggestions about selling or changing the magazine. Shareholders are probably screaming that change needs to come. Investors are now excited about the possibility that Freedom Communications's Scott Flanders might be offered the top job.

But is the excitement justified? The company's latest quarterly results were pitiful as usual, showing a net loss of $13.7 million, or 41 cents a share, compared with a loss $8.7 million, or 26 cents a share, the previous year. Playboy magazine revenues were down 16%, to $13.5 million, and the company forecasts a 39% drop in second-quarter ad revenue. That's understandable, given the state of the economy, but still horrendous.

Playboy's problems are well-known: the explosion of free online adult content, the shift of advertising online, and the huge numbers of magazines targeting the young male audience, a category Hefner pioneered more than 50 years ago. But what may be killing Playboy faster than anything else is Hefner's libidinous lifestyle in the Playboy Mansion, which the company owns. These days, the 83-year-old, silk-pajama-clad swinger must feel like a prisoner of the brand he created: an aging King Lear, surrounded by a silicon-enhanced harem.

See more iconic American companies on the brink.


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