Since its inception in 1953, Playboy has been the gift that keeps on giving to men around the world. However, that’s not to say that every Playboy model has been as sizzlingly attractive as Joana Krupa. In fact, sometimes Playboy sets its sights on sad, attention-starved starlets simply for the PR. Take Tara Reid, for example. Her spread will draw in many readers more interested in the train wreck than the scintillation. Similarly, sometimes Playboy snags some real hotties, but only gives us a small slither of nudity pie – not exactly what “readers” are seeking from the magazine. As 2009 draws to a close, we decided now is as appropriate of a time as ever to compile some of Playboy’s worst cover girls in the mag’s history. Of course, for the record, we’d probably still sleep with them all.
La Toya Jackson (March 1989)
Known mostly for her scandals through the 80s and 90s, her personal drama eclipses her haphazard “career.” It’s a small wonder that she would lend credibility to the sexual abuse allegations against her brother Michael. For the first time in her life, she wasn’t the bad Jackson. To make matters worse, the bleached skin in her Playboy spread made her resemble her infamous brother.
Lisa Guerrero (January 2006)
If there are two things that men love, it’s sports and women. But they also love a third thing: full nudity. Unfortunately, Lisa didn’t deliver on the naked. Readers were more likely to get aroused by a lingerie catalog than her issue. I’m not saying I haven’t used a JC Penney catalog when I was desperate, but come on Playboy! I expect more from you.
Paris Hilton (March 2005)
Because of her excessive privileges, careless antics, and air headed comments, those in the world who don’t hate Paris Hilton are few and far in between. Chances are that even Tiger Woods has a higher approval amongst the Swedes. Not only was her Playboy spread undesirable, but it was also completely unnecessary. After all, a much more graphic videotape of Paris was only a click away.
Jessica Alba (March 2006)
Jessica Alba stands out as an exception on this list. While she’s certainly gorgeous enough to honor Playboy with her presence, she never actually consented to appearing in it. The cover itself was a poorly photoshopped image from her 2005 movie, Into The Blue. This ultimately sparked a lawsuit, which was later dropped after an apology from Hugh Hefner. Lawsuits are not sexy.
Tara Reid (January/February 2010)
Recently, Playboy seems intent on showcasing C-listers, has-beens, and washed up actresses. Tara Reid falls under all three categories. This once-for-a-brief-period-of-time hot Hollywood starlet was in demand 10 years prior to her Playboy cover shoot. Her brief stint on E!’s “Wild On” rendered her a professional drinker, a profession that has steadily taken its toll. A botched-up liposuction gave her stomach the appearance of a shrunken prune. Tara Reid is a perfect example of the old adage “too much of anything is bad.” This doesn’t exclude plastic surgery.
Joan Laurer (November 2000)
Chyna’s (Joan Laurer) first foray into Playboy was one of the best selling issues of all time. However, the majority of consumers weren’t convinced that she was a woman. Playboy apparently didn’t care, as they invited her for another spread.
Kendra Wilkinson, Holly Madison, Bridget Marquardt (March 2008)
One of the great things about Playboy is that you don’t have to hear the airhead models talk. Even if they say something stupid in a Q & A, you can simply ignore the text and look at the boobs. This is not the case with television, and it’s the primary reason why “The Girls Next Door” is such an annoying show. You have to listen to every stupid thing the bimbos say, and there is no nudity to make up for it. Once you’ve heard such stupidity, it’s hard to put the genie back in the bottle. So when Playboy put "The Girls Next Door" on the cover, all people could think to themselves was "Shut the hell up you vacuous neighbors!"
Darva Conger (August 2000)
Remember that game show “Who Wants to Marry a Millionaire?” The show itself was a beauty pageant where women competed to wed a millionaire. Controversy ignited when the winning contestant, Darva Conger, remained married for only 3 days before annulling her marriage. What made matters worse was the revelation that Rick Rockwell, the alleged millionaire, not only wasn’t rich, but had a restraining order filed against him by a previous girlfriend. After the uproar died down slightly, Conger consented to a Playboy spread under the premise of giving the world a glimpse of what Rockwell didn’t see. Conger wasn’t exactly bad looking, but neither was she Playboy material.
Marge Simpson (November 2009)
Let’s get one thing straight: Marge is about as hot as cartoon characters come. But Playboy gets the thumbs down on this one since they were basically just ripping off Maxim’s 2004 spread of the luscious Springfield native. It’s impossible to skim through this issue without feeling like a weirdo, and one with a blue-hair fetish, no less.
Carol Alt (December 2008)
Yes, Carol Alt was gorgeous and still is for her age. However, some models should have a nude expiration date. After declining to pose for Playboy for decades, the mag should’ve turned her down in 2008 for acting like the former prom queen who only shows interest in the geek once she’s past her prime.
Amanda Beard (July 2007)
There are a number of female athletes out there, but few attractive ones. The reason? Well, to be frank, because exercise “masculinizes” their bodies. Such was the case for Olympic swimmer Amanda Beard. With shoulders like hers, it’s difficult not to associate her with the cross dressers lingering around Hollywood Boulevard.
Heidi Montag (September 2009)
Aside from Paris Hilton, Montag probably stands as the second most hated woman in America. Her hubby, fellow “Hills” reality star Spenser Pratt, is perhaps third on the list. While Montag is attractive in that uber Hollywood sort of way, the reality TV diva doesn’t even appear nude in the spread. For shame, Playboy.
Caroline Cossey (October 1985)
Yes, this former Bond Girl was beautiful. Yes, there are a lot of people who would still find her desirable in spite of her once well-kept secret (that she’s really a dude). But as a general rule of thumb, it’s easier to fawn over Playboy models when you know they haven’t changed genders at some point in their lives.
Sandra Bernhard (September 1992)
Speaking of trannies, here’s Sandra Bernhard. No one in their right mind wanted to see Sandra naked. Everything from her gap-toothed smile to her lopsided chin is more than likely to kill the mood rather than spice it up. But hey, she’s funny, right? Oh, wait, she isn’t.
Patti Davis (July 1994)
Another woman famous for being famous, President Reagen’s daughter undoubtedly graced Playboy’s pages in a bid to rebel against her parents. While she’s in the upper crust of attractive first families throughout history, she was never really suited to win beauty pageants. But again, we certainly wouldn’t kick Davis out of bed.
Kira Kener, Dagmar Kozelkova, Tera Patrick (March 2002)
Readers accustomed to Playboy shouldn’t feel an aversion to pornography. However, this spread was just downright trashy. Besides, if you wanted to see these three porn stars naked, you could just see them in action with a quick Google video search.
Faye Resnick (March 1997)
Playboy seemed intent on chronicling everything wrong with the 90s. Resnick served as a key witness in the O.J. Simpson trial, alleging that Simpson stalked his ex-wife in the days leading up to her murder. Not one to let a good murder go to waste, Resnick posed in a Playboy spread after the trial ended, showing off the worst plastic surgery money could buy.
Jerri Manthey (September 2001)
Like many Playboy cover girls, curiosity about Jerri Manthey fueled sales more than her attractiveness. While most people build careers based on hard work and talent, Manthey distinguished herself through reality television. While she stood out during her time on “Survivor: The Australian Outback,” Playboy would have been just fine if she stayed in the bush.
Shannen Doherty (December 2003)
Shannen Doherty appeared in Playboy multiple times: once in 1993, twice in 1994, and thrice in 2003. No one’s going to deny that she was attractive in the early 90s, and that she’s still a looker for her age, but her latest appearance was past her point of relevancy. Not only is “Beverly Hills: 90210” off the air, but she hasn’t starred in a hit since then. If the so-so TV show "Charmed" rejects you, you shouldn’t be Playboy material.
Jessica Canseco (September 2005)
It really says something about you when your claim to fame is nothing more than your previous marriage to juiced up athlete Jose Canseco. It says even more about you when you milk it for every cent. Talk about losing a battle with dignity.
Anna Faris (September 2008)
No one’s arguing that Ana Faris isn’t cute. However, what separates Playboy from every other men’s magazine is its share of tasteful nudity. There was none of that in this issue. The bland cover was matched with an equally bland spread that looked like something straight out of US Weekly.
Sarah Kozer (June 2003)
Kozer was the runner-up on the “Joe Millionaire” reality series. Much like “Who Wants to Marry a Millionaire,” the premise of the show was to focus on a group of women slobbering over a man’s alleged riches. Kozer stands as a moderately attractive photoshopped cover girl who was lost to obscurity after her 15 seconds climaxed. The article’s headline, "What Joe Millionaire Missed," neglects to realize that Joe Millionaire most likely picked up a copy of the article himself.
The Women of Enron (August 2002)
Hey, remember that horrible financial scandal where thousands of people lost their jobs? The first thing I thought when I heard about that was, “when am I gonna see those sad unemployed ladies naked?" The answer: right away (probably because they needed the money). Taking advantage of one of 2002’s biggest news stories, Playboy offered former and current Enron employees a chance to become cover models. Many entered the contest, but it was humanity that lost.
Lisa Rinna (May 2009)
Plastic surgery can work wonders, but not for everyone. No amount of Photoshop could mask what this “Days of our Lives” star willingly paid to have done to herself. Good lord, how can she get any food past those ginormous lips?
Tuuli Shipster and Kiera Gormley (October 2009)
While these two models aren’t bad looking by any means, they don’t really belong in Playboy. Truth be told, the real reason they made the cover is because Playboy was trying to cash in on the Twilight-induced Vampire fad. There’s something very wrong about mixing Playboy and a movie aimed at 12-year-old girls.