Playboy was first issued in December 1953 and to kick it off, they put Marilyn Monroe on the cover. The blonde bombshell helped put the magazine on the map and almost 60 years later the magazine is still going strong.
LaToya Jackson posed for Playboy in March 1989, after leaving her father as her manager and trying to make a name for herself. She went on to pose for the magazine in November 1991. The first cover was one of the most sold for the magazine at the time, with eight million copies sold.
Mariah is never one to be too shy and wants to flaunt her body, at least when her body is in the shape that she likes. She had a disaster on her hands with Glitter and to redeem herself, she was releasing The Emancipation of Mimi and decided to pose for Playboy to gain some more publicity. The pop diva did keep her clothes on though.
Downtown Julie Brown was a hit on MTV in the 1990s when she was a VJ and host of the show Club MTV. She was popular and to keep her fans intrigued, she posed for Playboy in August 1998.
Carmen Electra got her start dancing with the Pussycat Dolls and then went on to star in Baywatch and MTV’s Singled Out. She has appeared in movies, but can pay her fame to her appearances in Playboy. She first appeared in May 1996 and has been on the cover three other times
Supermodels have been talked into posing for Playboy many times and Cindy Crawford is one of those models. She has since gone on to make a fortune for herself with her cosmetics and household goods line, but before all that she made the cover on July 1988 and October 1998
Pamela Anderson holds the record for appearing on the cover 13 times! She first appeared in the February 1990 issue and then appeared many times throughout the 1990s and 2000s and made her 13th appearance in January 2011
Naomi Campbell had a lot of issues going on in the late ’90s, with the phone assault on her assistant and a trip to rehab for a cocaine addiction, but she tried to get that attention off of her bad things and she posed for Playboy in December 1999.
Another supermodel who decided to grace the cover of Playboy is Elle MacPherson. She decided to pose for the cover back in May 1994 and has since moved on to bigger and better things with her show Fashion Star on NBC
Tara Reid made a name for herself when appearing in American Pie. She has since become a hot mess and appeared to be drunk at many events and had a Wardrobe Malfunction on the red carpet, but it was enough to want everybody to see everything in the January 2010 issue.
Jenny McCarthy started her career back in 1993 when she posed for Playboy. She went on to become the Playmate of the Year for 1994 and has since appeared in the magazine six times. She posed for the July/August 2012 issue, nearly 20 years after her first appearance
Lindsay Lohan has been a hot mess over the past few years and can’t seem to keep herself out of trouble with the law, including her recent arrest for punching a girl at a bar. Why doesn’t Lindsay just stay out of the bar? She was broke and needed some money, so Playboy offered up some dough and Lindsay accepted and appeared in the January/February 2012 issue.
This was one that caused an uproar for Playboy. An image of Jessica Alba appeared on the March 2006 issue, but it was without her knowledge. She sued the publication, but the lawsuit was dropped eventually. She is known as a sex symbol, so shocking she hasn’t bared it all for Playboy.
Kim Kardashian pretty much made a name for herself via a sex tape she made with Ray J back in 2007. She is now known for the family reality show Keeping Up with the Kardashians. Anyone whose watched the show knows that her Mom helped manage the December 2007 cover of Playboy.