Playboy Enterprises Inc.'s 39 years as a public firm, which will come to an end with its buyout deal announced Monday, turned out to be the embodiment of that old line about how to become a millionaire in the stock market: Start with $2 million.

Founder Hugh Hefner has agreed to buy out minority shareholders at $6.15 a share. He’s putting the stock out of its misery: As the Playboy empire has waned the shares have plunged 82% since peaking in 1999 at $33.44, a brief spike fueled by the Internet mania of that era. And measured back to 1990 the stock price has made no net progress in two decades.

Playboy looked like a hot investment idea in late-1971, when Hefner decided to take the company public by selling 1.2 million shares and listing on the New York Stock Exchange. It was still Hef’s world back then: The magazine’s circulation was climbing rapidly, membership in his Playboy clubs was an American status symbol and the company was expanding into the luxury-resort business.

But shareholders endured a long history of poor management and missed opportunities, even before the Internet rewrote the rules of adult content and distribution. The rap on Playboy always was that it wasn’t run for shareholders. It was run for one shareholder -- Hef. That image was cemented in 1990 when the company shifted to dual share class ownership, allowing Playboy to raise capital by issuing non-voting shares without diluting Hef’s 70% controlling stake.

If there are any original investors (besides the 84-year-old Hef) still in the stock 39 years after it went public, they will be recording a big capital loss this year.

How the math works out: The stock was sold at an IPO price of $23.50 a share in 1971. In 1990, with the recapitalization, investors exchanged two of their original Playboy shares for one share of voting Class A stock and three shares of non-voting Class B stock.

So if you bought the stock in the IPO you paid a total of $47 for two shares. Fast-forward to the present: Now you have four shares worth a total of $24.60. You've lost 48% of your money over nearly four decades. And that's before adjusting for inflation.

In its 39 years as a public company Playboy shares had plenty of tradable rallies, including the late-1990s spurt. But as a buy-and-hold idea, the bunny was a bomb.

-- Tom Petruno