Playboy’s Bunny Couldn’t Make the Hop to the Web

What the hell happened to the sort of man who reads Playboy? How could he let the Internet develop into the world’s strip club — and worse — without taking Hugh Hefner’s company along for the ride?

There’s no long tail for the Playboy bunny, judging from the rumored impending sale of Hefner’s company for around US$300 million to Iconix, collector of apparel brands like Candies and Joe Boxer. The 83-year-old Hefner, who for better or worse helped change the way the U.S. thought about sex, will have to spend his remaining days on Earth watching the bunny head logo he turned into a global brand show up on all manner of clothes. More than a tad ironic when you consider he made his name talking women out of their threads.

I doubt there will be many tears shed for Hefner, who is no longer the lightning rod for controversy that he was in the swinging ’60s, but — thanks to willing centerfold girlfriends, pharmaceutical magic and reality TV — can still inspire cheers and disgust, depending on your prejudices. Yet I find it amazing and yes, a little sad, that a man who was one of the first to storm the barricades of censorship and 1950s puritanical thinking couldn’t conquer 21st-century cyberspace. You can indulge any desire on the Web for a few bucks and a password. How could Playboy Enterprises not find a lucrative place somewhere on the sexual spectrum between Maxim‘s Web site and yournastyfetishhere.com?

The answer, of course, is that what helped make Playboy helped sink it. Playboy and Hefner’s image went from smart sophistication to, dare I say, quaintness, all of a piece with the spiral of ’60s cool that on the Fictional Secret Agent Scale started with James Bond, began trending downward with Derek Flint and bottomed out with Austin Powers. The joke eventually was on Playboy, baby.

Age and changing attitudes tend to do that, which brings us to Web ethics and its lack of a business model. It must have galled Hefner to watch his centerfolds show up for free on Usenet groups in the mid ’90s, as the Web began to blossom and Playboy was still floundering around with a digital strategy.

Here’s another irony you can put in your Hefner pipe and smoke: The same urban sophistication that helped protect and legitimize Playboy as it battled conservative critics from the ’50s through the ’80s would work against the company with the rise of the digital age.

All this puts Hefner right up there with the music industry as Internet roadkill. It didn’t have to be this way, Hef (can I call you “Hef?”). The right digital plan and marketing could have helped keep the Playboy bunny hopping even as its magazine circulation declined and its Playboy Clubs shut its doors (except for Vegas — naturally. See “Hangover, The.”)

It’s not too late. Playboy could establish itself as the “clean” sex alternative to all the dankness on the Internet. Playboy could rise again.

Without the aid of Viagra.

Playboy‘s Fledgling Web Strategy

Is there such a thing as tasteful porn? Would users of Web porn even bookmark Playboy.com? Steven Watts doesn’t think so, and he says that’s the way Hefner wanted it.

“With the magazine itself, and I suspect probably with the Web as well, Hefner — for all the scandal he created in his lifetime — always wants to present what he would call a quality product in good taste. He doesn’t view himself as a pornographer,” Watts told me during a phone conversation.

Watts, a professor in the University of Missouri’s history department specializing in American intellectual and cultural history, last year published Mr. Playboy: Hugh Hefner and the American Dream, a 700-page biography. It chronicles Hefner’s rise from sterotypical Midwestern roots to his $600 gamble on the first edition of Playboy magazine — featuring nude pictures of an ingenue named Marilyn Monroe — to the building of a media empire that spanned a TV show, nightclubs, movies, jazz festivals and a really big black airplane with its own disco.

Somewhere in that history, Playboy did try to create a Web presence under former CEO Christie Hefner’s leadership, but found itself battling the natural evolution of sexual attitudes it started in traditional media, Watts said. “The basic difficulty was that there are so many erotic images and sexual material of one kind of another available on the Web for free, the company was simply unable to attract a big enough audience to pay for the kind of stuff that they tried to establish. It never really got off the ground.”

Yet within the company during its heyday, there were marketing and editorial visionaries who knew how to play to the right demographic. The first line of this column plays off the famous “what sort of man reads Playboy” one-page promotional campaigns that showed up in the magazine in the ’60s and ’70s with the purpose of luring potential advertisers. Boston-based ad copywriter Paula Zargaj Reynolds’ very cool blog, Found In Mom’s Basement, features some of these pages. Here’s some sample copy, appearing with a picture of a man in riding togs about to take his horse out in what looks like his personal equestrian arena — Central Park:

“Having more disposable income than most, he can afford to keep a loose rein on spending. Fact: Playboy is read by 7,655,000 men who live in the country’s major metropolitan areas. And Playboy reaches more than 3,711,000 males with household incomes of $10,000 and over. Shouldn’t you find out more about this blue-ribbon market before you make your next media decision?”

Naturally, a blonde in the picture’s background is giving the man the once-over. Somewhere, “Mad Men’s” Don Draper is smiling and firing up a Camel.

A slice of retro Americana, certainly (dig that vintage household income). Yet it proves Watts’ point that Hefner always shot for respectability, even as his magazine was pushing what was a much narrower envelope in the late ’60s.

We’ve heard too often about porn’s estimated billion-dollar business on the Web. Nobody knows exactly how much money porn generates on the Internet; they just seem to know it’s a billion-dollar business. You’ve also read countless times about adult Web sites pioneering advances in Internet technology, including streaming video and security authentication. That kind of juggernaut owes something to Playboy and Hugh Hefner, and attitudes that tolerate more and more explicit images are bound to chase some people back to the good ol’ days of tasteful adult entertainment. And therein lies Playboy‘s chances at a second life.

The New Bunny Web Strategy

I’m not here to debate the deleterious effects of Web porn, or the impact Playboy had on men’s attitudes and the objectification of women. There are arguments to be made on those fronts, no doubt. This column is examining the Web’s impact on a pioneering American business. You may look at Hefner now and, depending on your view of the man, see a sad old guy forever chasing the fountain of youth in his pajamas, doomed to guest appearances on “Entourage.” I see an only-in-America original, a self-made success story. Like many, many other American men of a certain demographic, I read Playboy — for the articles AND the pictures — and let it imprint my psyche.

That’s why it’s hard for me to fathom how one of the top brands in the world, up there with Coca-Cola in my opinion, couldn’t make it work on the Web. Look at Playboy.com now. What do you get for free? A few nude pics and short videos, sure, but you also get full access to Playboy Interviews, including classic ones with John Lennon, Kurt Vonnegut and Arthur C. Clark. You get an excerpt from The Original of Laura, a Vladimir Nabokov novel dug up by his estate, along with related previous articles and interviews about the author of Lolita.

On the subscription side, you get plenty of chances to ogle more naked women if you pay anywhere from $20 a month to $8 a month, depending on whether you sign up by month or year. Some of those pictorials include some notorious celebrity nudity, like Cindy Crawford and the late Farrah Fawcett. (Would these actresses and supermodels have undressed on camera for just any adult entertainment company?) Playboy also provides mobile services and offers access to other subsidiary sites through package deals.

None of this was apparently paying enough to keep the magazine from seeking suitors for a sale. I suspect Iconix will consider shutting down all editorial operations, including the Web site, and focus on exploiting the bunny head logo. One way or another, overhead costs will probably result in the magazine joining Look, Life, Colliers and the Saturday Evening Post in the Museum of Extinct Publications.

The Web site could survive, I believe, in one of two forms: It could embrace the Web’s dark side by offering up more explicit content that Hef would have frowned upon, or it could position itself as a more tasteful adult entertainment, one worthy of Hefner’s praise, while also figuring out ways to monetize the classic print content — perhaps e-reader deals, or finding some other way to make use of its storehouse of articles. If Maxim is the tease king of the lad mags, then Playboy.com could sell itself as the Web site that gives you more — more skin, more articles, more lifestyle stuff for men. A reinvented Playboy Web site could also take up Hefner’s mantle of conservative scourge by being more aggressive with a political philosophy. The current issue takes on Glenn Beck; why not build on that?

If the aforementioned “Mad Men” can find an audience with its retro look at American advertising and lifestyles, than why can’t Playboy, which was there when it all started? Everything old can be new again. And think of the money the company will save on staples.