10 Celebrities Who Ruined The Cover Of Playboy

Playboy is an iconic magazine started by magazine mogul Hugh Hefner back in 1953. Hef created an absolute gold mine when he tapped into the male audience seeking pictures of beautiful women. Of course

Playboy is an iconic magazine started by magazine mogul Hugh Hefner back in 1953. Hef created an absolute gold mine when he tapped into the male audience seeking pictures of beautiful women. Of course, we can't leave out those in depth articles (ha-ha) which pretty much are white noise next to photo spreads of sprawled out naked women and their sexy poses. Playboy has been in our vernacular for over a half century and is still as strong a brand today as it was yesterday. Despite competition from everyone and everywhere, Playboy is still the foremost magazine on sexuality with a splash of class.

Playboy does a lot of things right. They have been able to capitalize on trends and pseudo celebrities at the right time. They also have found the newest diamonds in the rough for us to go cover and enjoy their beauty. Playboy has helped launch the careers of many women who needed the exposure to find their own piece of fame. Now Playboy, like anything else, isn't always perfect. There are going to be a few speed bumps no matter what you do. And some celebrities who have dawned the pages of Playboy probably weren't the best choice to end up there. Playboy’s brand is so strong we demand the highest in quality, and frankly, we expect it. These are 10 Celebrities Who Ruined The Cover Of Playboy.

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10 La Toya Jackson


The mere mention of La Toya Jackson and Playboy in the same sentence is frightening enough. We all know the power of the Jackson family name but we didn't know it was strong enough to place La Toya on the cover of the prestigious Playboy. Hugh Hefner made us suffer through this ill-advised cover spread by one of the most notorious and untalented Jacksons to walk the face of the earth. La Toya is the “Look at me!” Jackson, begging for attention that has escaped her during her life. We are still scratching our head why Le Toya and all of her makeup ever appeared on the cover but we can make the assumption it will never happen again. And thank God for that.

9 Sandra Bernhard


Sometimes you just have to shake your head and do a double-take when you see a certain person who is chosen for the cover of Playboy. They usually get it right but once in a while they try to shock the world with a celebrity we never thought could possibly ever dawn the cover. This is the case with Sandra Bernhard who dawned the cover of Playboy back in September 1992. Neither beautiful nor sexy, Bernhard who is known as a dramatic and comedic actress with the ability to sing, somehow landed a Playboy spread. We're not sure which men were actually fantasizing about the singer/actress. She easily rings as the worst celebrity cover of all time according to a poll conducted by Classic Rock 961 (and that’s with La Toya Jackson on the list!).

8 Heidi Montag


One of the stars of the television reality show, The Hills, Heidi Montag enters the list of one of the worst celebrity Playboy covers of all time. Desperate for attention and for any celebrity status she could get her hands on, Montag has tried to use the reality series to propel what little career she has had. She also has undergone a multitude of plastic surgeries in order to keep herself on the covers of magazines. The extreme nature and desperation displayed by Montag are no reason for her to be on the cover of Playboy magazine. The extreme nature of her dozens of plastic surgeries is more cause for alarm and a cry for help than a pat on the back and a cover spread. However, due to the circus that was surrounding her during her declaration of all the plastic surgeries, Hefner and company decided to take her on and gain extra attention. Again, the public would not be fooled as very few were interested in seeing Montag on the cover of the storied magazine.

7 Ashley Dupre


We might as well get a wannabe celebrity out of the way first. Ashley Dupre was a high-end call girl. She got notoriety for being the mistress/prostitute of Eliot Spitzer (former Governor of New York). Once she was able to get some news coverage over the incident she capitalized by posing naked for Playboy. Playboy is never shy about tackling the flash-in-the-pan celebrities. Dupree even followed up her Playboy shoot by dabbling in a comical singing career. Her Playboy cover will go down as one of the worst of all time and one of the most undeserving. The overhyped call girl was nothing more than a pretty girl trying to make some big cash by selling her body for sex. This is not what we were hoping to see on the cover.

6 Carnie Wilson


Carnie Wilson is a talented singer and daughter of famous Beach Boy Brian Wilson. Carnie also happened to make quite a bit of waves when she sang the hit song “Hold On” in the trio group Wilson Phillips. Now Carnie did an excellent job dropping a lot of the extra weight she held on her body which was clearly unhealthy. But when she sang for Wilson Phillips, she was third banana in terms of beauty and sex appeal. Losing the excess weight doesn't mean we should slap her on the cover of Playboy. Carnie was excited to share her new look with the world and Hugh Hefner was more than happy to throw her on the cover. Again, this seems like a pretty big mismatch as there weren't too many men wanting to see her on the cover in the first place. We applaud Carnie while at the same time wagging an angry finger at Hef.

5 Downtown Julie Brown


Well, "Downtown" Julie brown is a name we remember from the 1980s. She was an MTV VJ who had a little bit of sass and enjoyed her role of being a temporary television celebrity. But when MTV and videos started to dry out, the VJs went away and so did Downtown Julie Brown. So what do you do when you get no more attention and you want to be recognized? Naturally, you pose for Playboy. In 1998, long after the “legend” of Downtown Julie Brown had faded, she appeared on the cover of the magazine. Downtown Julie Brown will definitely not go down as one of the sexiest women to dawn the pages of Playboy. In fact, it is shocking that she was chosen to be on the cover to begin with. With that said, she isn't the worst pseudo celebrity to ever be on the cover of the storied magazine but she definitely was a bad choice.

4 Shannen Doherty


Aaron Spelling's favorite television girl, Shannen Doherty, has had an infamous run on a couple of his shows. She is one of the few actresses that has torpedoed her career not once, but twice. Known as a very difficult person to work with, Doherty was the lead character on two different successful Aaron Spelling series. However, she wore out her welcome when her demands and attitude proved too much. Her ego got her booted from the two shows and she was desperate for one last celebrity gasp. Still hanging on by a thread in the public vernacular, Doherty opted to take some cash and take off her clothes on whatever celebrity juice she had remaining. Television’s bad girl drew little interest as everyone was tired of her crappy attitude.

3 Brigitte Nielsen


Brigitte Nielsen is a very interesting character to say the least. Known as the sexy Russian girlfriend to Ivan Drago in the feature film Rocky IV, Nielsen is a model and actress who never really succeeded too much in either field. Nielsen posed for Playboy back in 1987 when she was at her celebrity status peak. And back in the glory days in the 1980s, she was decently hot. Her celebrity status faded as quickly as the best of the Rocky films; and later in life she was connected as the girlfriend of Flavor Flav. Plastic surgeries, substance abuse, alcohol abuse and a whole long laundry list of things that were going wrong in Nielsen’s life have made her a very poor cover choice. More of a punchline than anything else, Nielsen was put on the cover of Playboy and her career never took off, and in fact, evaporated quicker than you can say "butch haircut."

2 Chyna


Combine some sex appeal and a lot of steroid-like charm, and you have the creation known as Chyna. Born, Joan Marie Laurer, Chyna is a former professional wrestler, an actress, a bodybuilder and she also dabbles in pornographic films. She came on the scene in 1997 for the WWF. She performed under the name of Chyna and was billed as the “Ninth Wonder of the World.” Chyna has dawned the pages of Playboy twice (once was more than enough), had a sex tape released, and starred in 5 other pornographic films. Chyna has also battled drug and alcohol addiction and appeared on Dr. Drew’s Celebrity Rehab Show. Chyna has also been arrested for domestic violence. Clearly, there may be some sex appeal for those who like muscular women, but she has been an absolute mess and isn’t worthy of the cover of a magazine with the status of Playboy. She also isn’t hot either. So…what the hell.

1 Marge Simpson


Okay, we get it. This is a publicity stunt to throw out the Simpson’s name and garner some extra pub for the magazine. But there is nothing interesting to me about a middle-aged cartoon character (assuming anyone wants to see any cartoon characters on Playboy to begin with) dawning the cover of this magazine or any other. There have been numerous celebrities who were on the cover who didn’t take their clothes off which upsets and disappoints fans to begin with. But tossing in a silly cartoon character makes this look a lot more like The New Yorker than Playboy. We’re not looking for irony or cleverness in Playboy, we’re looking for hot naked ladies. This is not kosher in our book. Don’t waste our time. Not only is Marge Simpson not sexy, but this is the most ridiculous Playboy cover of all time and ruins what the covers are supposed to be all about.

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10 Celebrities Who Ruined The Cover Of Playboy