Penthouse used to be the sleazier also-ran to Playboy's (ever-cheapened) aspirationalism. During the boom years, Penthouse made a bid for respectability, hiring an editor from GQ and — the true mark of fashion bonafides — convincing Terry Richardson to shoot Sasha Grey for the magazine. The idea was to make a classy, visually appealing Penthouse, at a time when luxury was a word everybody loved. It ended with that editor being escorted from the building, a return to Penthouse as "hard-core sex magazine," and a focus on the company's truly promising properties: the FriendFinder family of sites, which currently nets $330 million a year. "Penthouse" was even taken out of the name — the company also runs Bigchurch.com, aimed at Christian singles — and it's now known as FriendFinder networks. (You can have all kinds of friends.)
Meanwhile, Playboy tried to make up for the stultifying sameness of its brand by appealing to women, with The Girls Next Door and Playboy Bunny merch. As for the magazine, it has held on to its patina of respectability, with some real journalism, but hasn't continued to make itself essential in a change world.
Here's why: 1) If you want high-end photography to go along with your titillation, you can read GQ; if you want highbrow writing about sex, you can read Nerve or sundry personal blogs. 2) Sexual tastes are far more diverse and dynamic than either of these magazine ever gave them credit for being. 3) People can instantly find real sex, either images of it or the IRL kind, online.
Though Hefner has dismissed FriendFinder's approach as a publicity stunt, that company's CEO told Bloomberg, "Our interest is mostly the digital assets," adding, "We have no desire to throw him out."
If Hefner keeps FriendFinder at bay and succeeds in getting the company back in his sole control, he will probably keep doing what he's been doing, accompanied by a shifting assortment of blonde girlfriends, until the day he dies. The rest of the world will have moved on.