The relationship between the WWE and Playboy began when Sable appeared on the cover of the April 1999 issue. Within months of the release of the magazine, Sable left the WWE and reappeared on the September cover of the magazine. Shortly after that, a magazine dedicated exclusively to Sable and her two pictorials hit store shelves. This made Sable the first woman in Playboy history to appear on three different magazine covers in one year.<p>Chyna appeared on the cover of the magazine in the fall of 2000. The following year, she left the WWE and in 2002 she reappeared on the cover of <i>Playboy</i>. Unlike <a href="https://www.thoughtco.com/biography-of-wwe-diva-sable-2787399" data-inlink="akGtOOhmJzupMB0ee4S8EA&#61;&#61;" data-component="link" data-source="inlineLink" data-type="internalLink" data-ordinal="1">Sable</a> who got a special magazine after her second appearance, Chyna instead was given a video diary entitled <i>Joanie Laurer, Nude Wrestling Superstar</i>. This would not be the last time that Chyna would appear nude. In 2004, a sex tape, entitled <i>One Night in China</i>, featuring her and X-Pac was released.</p>Torrie Wilson appeared on the cover of the May 2003 edition of the magazine. Unlike, Sable and Chyna, she would still be employed by the company by the time she appeared on the cover of the magazine again.<p>By 2004, the bad blood between Sable and the WWE ended and she was back in the company. The March 2004 edition of <i>Playboy</i> featured Sable and Torrie Wilson share the cover and pose in a pictorial together. This magazine marked the beginning of the annual Diva appearance on the cover of the magazine right before <i>WrestleMania</i>. At <a href="https://www.thoughtco.com/shawn-michaels-wwe-career-timeline-2787747" data-component="link" data-source="inlineLink" data-type="internalLink" data-ordinal="1"><i>WrestleMania XX</i></a>, the two women teamed up in a Playboy Evening Gown Match and beat the team of Stacy Keibler and Jackie Gayda.</p>In 2004, Christy Hemme was the winner of the first televised Diva search contest. The last woman she beat out for the honor was Carmella DeCesare, the 2004 Playmate of the Year. Christy would follow in the footsteps of Carmella and take off her clothes for Playboy. Christy appeared on the April 2005 cover. Christy would go on to leave the WWE that December.Even though Christy won the Diva Search contest, Candice would go onto greater things in the company despite not even making it to the fan vote of the 2004 contest. Candice garnered additional fame for appearing in the controversial Super Bowl ads for GoDaddy.com. Candice appeared on the cover of the April 2006 edition of the magazine. In 2007, Candice won the WWE Women&#39;s Championship. Candice was the first WWE Diva to appear on the cover of the magazine that had prior nude work released. She was in an episode of <i>Hotel Erotica</i> and was a Playboy Cybergirl in June 2002.Ashley Massaro was the winner of the 2005 Diva Search and appeared on the cover of the April 2007 edition of <i>Playboy</i>. Just like Candice, Ashley had modeled for Playboy prior to becoming a part of the WWE. Using the name Ryan MacKenzie, she had appeared in one of Playboy magazine&#39;s special edition magazines in 2004.With Maria&#39;s appearance on the April 2008 edition of the magazine, it marked the third time in four years that a contestant from the 2004 Diva Search went on to become the cover girl of a WWE-themed edition of Playboy. Unlike the Divas that appeared on the cover the prior two years, this pictorial marked the first time that naked photographs of Maria were seen by the public.