Playboy (PLA) tends to be associated with the magazine and sex. Not the hardcore, nasty kind, of course -- Playboy has always been more than a tad distinguished, staying above board while the adult entertainment industry has chosen to compete in ways that my editor would delete if I even attempted.

With Iconix said to be interested in acquiring Playboy, it needs to think about where it can win with the ailing brand. The smart move may be to ditch the magazine and move away from sex -- it can't compete in either of these markets. Then, it needs to figure out how to make the brand relevant to everyone not in the Boomer generation ... or treat Playboy as an investment with a clock on it.

Playboy is such a mess that even the hint that a company is interested in it triggers a reaction. Oak Hill Capital Partners, a private equity firm, announced Wednesday that it has no interest in buying ailing adult media company Playboy (PLA), despite previous media reports indicating the contrary. Of course, this sent Playboy's shares down 3.7%. Oak Hill didn't just say "no way" to the present but made it clear for the future as well.

This follows a statement by Golden Gate Capital that it wouldn't be involved in a Playboy acquisition, again, despite suggestions in the media that it might make a move for the bunny. The latest possible buyer is Iconix Brand Group, which is generally hungry for brand acquisitions. Playboy is keeping its mouth shut on the matter.

It's wabbit season!

There's only good news for Playboy (PLA) when someone expresses an interest in buying it. Shares of the ailing men's lifestyle company shot higher on Thursday when word got out that Iconix is interested in acquiring it. Iconix owns and licenses brands to manufacturers and counts Candie's and London Fog among its holdings. A deal isn't a sure thing, but Playboy now has something it hasn't in a while: hope.

Iconix has been looking to acquire more brands. And Playboy has been looking for a knight in shining armor (and with a hefty war chest in tow) since at least June, when Scott Flanders took the helm. But it looked like acquisition bait well before then, thanks to a rough financial situation.

Playboy (NYSE: PLA) published its Q1 results today. Any longtime follower of the company will note that things haven't changed. We're still talking about revenue declines and losses. When will the Bunny finally hop back into reliable profitability? No one really knows when (if) that will happen.

On a reported basis, Playboy said it lost $0.41 per share. If you strip out charges, you get a loss of $0.15 per share. This number was a few cents better than the expectations of analysts according to this source. Be that as it may, they certainly don't meet my expectations. The adjusted loss is essentially the same as last year's number. I suppose we have to give the interim CEO Jerome Kern a chance. As you'll recall, Christie Hefner finally gave up her throne earlier in the year (thankfully).

Playboy Enterprises (NYSE: PLA) reported a loss of $145.7 million for the fourth quarter of 2008 -- $4.37 per share on a stock that trades right around $1.50. Revenues declined precipitously, but the real reasons for the loss were impairment, restructuring and other charges totaling $157.2 million.

The stock is trading up slightly today, perhaps in part because chairman Jerome Kern (not that Jerome Kern) told investors on a conference call that the company is "willing to listen" to listen to sale or merger possibilities, something that the company hadn't done under former CEO Christie Hefner's reign of terror.

Christie Hefner became the CEO of the company her father started in 1988, and it's been what could charitably be called a disaster for shareholders. Shares of Playboy Enterprises Inc. (NYSE: PLA) closed on Friday at $1.75. The stock traded at more than 5 times that price in the early nineties, impressive given that the company doesn't even pay dividends.

In a press release announcing her departure there was, of course, no mention of that: Hugh noted that " Of course, as her father, my first priority is Christie's happiness. While I will miss her leadership here, I believe that she will go on to achieve even greater personal success."

Awww. Ms. Hefner will remain as CEO until January 31st of 2009, and will stay on the board of directors until a replacement is found.

That a CEO could remain at the helm of a company for 20 years even as shareholder value evaporates is a testament to the power of nepotism in corporate America, and the unwillingness of independent directors to stand up and make changes.

The message for investors is this: Always be skeptical of a CEO who isn't the founder of the company but shares the same last name. It's possible that they really do deserve their title and are brilliant leaders but more likely, the monarchical rule will be to the detriment of long-term shareholders.

This post is part of a feature on companies and products that our bloggers think are in need of a makeover. See all 26.

They had to twist my arm to write about Playboy Enterprises Inc. (NYSE: PLA). At least that's the story I am telling my wife and I am sticking to it.

The problem Playboy faces -- as do other purveyors of adult entertainment -- is a simple: why buy a cow when you can get the milk for free. That's a crude and probably sexist metaphor, but an accurate one. Not only is the amount of porn on the internet mind-blowing, but increasingly it's free and can be accessed anonymously. For Playboy and its competitors, the problem is only going to get worse because the popularity of these sites appears to be soaring.

Wall Street already has little faith that the Chicago-based company can redeem itself. Shares in the company built by Hugh Hefner have dropped more than 82% this year. The company has been a mess for years. Net income in the second quarter was a puny $2.1 million, or 6 cents per share. Revenue fell 14% to $73.4 million as higher licensing revenue did not offset the declines in its media business.

Particularly worrisome was the loss in the publishing unit of $1.9 million following declines in circulation and advertising at the domestic edition of Playboy magazine. Advertising pages dropped a whopping 10 percent in the third quarter.

It's being reported that Playboy's (NYSE: PLA) Hugh Hefner's relationship with Holly Madison is over. Madison, as you probably know, was Hefner's head girlfriend, but he has two others as well: Kendra Wilkinson and Bridget Marquadt. The four of them star in a reality show called The Girls Next Door, which runs on the E! channel. It's a pretty fun show, although it does make me maddeningly envious of Hef's lifestyle. That aside, it seems to be a decent brand ambassador for the Playboy image. Unfortunately, the popularity of the show hasn't been enough to offset losses at the media company. Playboy's stock currently sits below $3 a share. It is the exact opposite of one of Hef's playmates: downright depressingly ugly.

Well, I can't really comment as to how the Hefner/Madison affair will turn out. Will she go back with him? Is this just a publicity stunt? I simply don't know. However, I would imagine that, with Playboy's stock in the dumps, a breakup might be an event that could be exploited to help out the company. Let's face it: the whole three-girlfriend thing is pretty much an orchestrated machine anyway. So, if Madison truly does feel like she's ready to move on with her career, I think Hef should clean house and get rid of the other two girls as well. Then, he could go on a search for three new girls next door (or maybe he should search for more, why stop at just three?). It could be an integrated media campaign spanning the magazine, the website, and a new reality show.

Playboy Enterprises, Inc. (NYSE: PLA) may not be doing so well, but it's still one of my favorite companies -- I'm a guy, so this makes sense. The company reported Q4 and full-year earnings today -- losses have widened, and I'm sure not a few investors out there are questioning the value of the brand.

Total net revenues saw a slight decline for the quarter, coming in at roughly $86 million. The company lost 3 cents per share on these revenues; in the previous year's quarter, Playboy actually booked a much more pulchritudinous 11 cents per share of positive net income. For the year, total net revenues didn't jump like a bunny -- $340 million versus $331 million. Net income, however, was much better, doubling to 15 cents per share. The company's year-end results benefited from a decline in interest expense, income tax obligations, and other costs. Sales of artwork were also cited by CEO Christie Hefner in the release.

The licensing operations are performing, but domestic TV and publishing are very weak. In fact, it is the publishing segment that really needs attention. It's been needing attention for a long time now -- for the year, subscription sales were down, newsstand sales were down, and advertising revenues rose by the smallest bit.

Long-term, I still have hope for Hugh Hefner's Playboy. It is an American icon, and its logo continues to propel licensing; plus, the company does have a nice presence in Vegas at the Palms Casino Resort. As Jonathan Berr reported back in November, you may want to remember that sex does indeed sell, and one has to assume that Playboy will be supplying that demand for years to come.

Playboy Enterprises Inc. (NYSE: PLA), much like its founder Hugh Hefner, continues to show signs of spunk. The adult-entertainment company today reported better-than-expected third quarter profit, helped by strong licensing sales and international TV revenue.

Shares of the Chicago-based company are up about 10% over the past six months. Playboy is gaining new pop culture relevance thanks to "The Girls Next Door" and that will be further helped whenever the big budget movie about Hefner gets made.

Playboy, though, is a small fish in a very big media pond. Net income for the quarter was $2.6 billion, or 8 cents per share, compared with $1.1 million, or 3 cents, a year earlier, beating Wall Street consensus forecasts of 6 cents. The revenue figure of $82.8 million -- only a 1% gain from the year-earlier period -- missed analysts' estimates of $86 million.