The Six Least Appealing Playboy Covers Of All Time

Look out, everyone. When you get your issue of Playboy in the mail this month – does anyone have a subscription to this anymore, anyway? – you might want to sit down before looking at the cover. While there’s still a good-looking female staring out at you, if you look a little harder towards the bottom there you’ll be greeted by seeing a dude on the cover!

That’s right. Funny man Seth Rogan is this month’s “cover boy”, the 9th gentlemen to grace the cover of the iconic magazine in its 56-year history. Why Playboy thinks that having a slightly overweight, goofy looking dude on the cover is going to help sell magazines is beyond me, but this isn’t anything new for the bunny empire. Since it first appeared on newsstands in 1953, Playboy has had its share of disturbing covers. Let’s go through the past five decades of archives and point out the worst ones:

The 50s


Throughout much of the 50s, the magazine put odd artwork instead of actual bathing beauties. Whether this was an artistic decision or the result of censorship laws is unclear. What’s clear, however, is that seeing a full-grown man in a bunny outfit staring back at you through binoculars is creepy as fuck. Even before Donnie Darko made it even creepier.

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About Rick Mosely Rick is the editor for TSB magazine.

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