Jennifer Jackson

Playboy

Jackson was chosen as Playboy's Playmate of the Month in March 1965, becoming the first African American to receive the honor. Jackson was discovered at age 18 while working as a Playboy Bunny at the magazine's Chicago club — the setting of the new NBC show The Playboy Club. Now Jackson lives a relatively tame life with her husband and three children in Washington state.

Darine Stern

Playboy

Stern became the first African-American model featured alone on Playboy's cover in Oct. 1971, 18 years after the magazine's inaugural issue. Stern's iconic pose was emulated by a bare Marge Simpson on the magazine's November 2009 cover.

Ola Ray

Epic Records/Playboy

In June 1980, three years before she became the unsuspecting damsel in Michael Jackson's seminal "Thriller" video, Ray was named Playboy's Playmate of the Month. She went on to be a regular in the pages of Playboy, posing for more than 17 pictorials throughout the '80s and '90s.

Jayne Kennedy

Playboy

Kennedy scored the Miss Ohio 1970 crown 11 years before she became the first African-American actress to grace the Playboy cover in July 1981. She posed with then-husband Leon Isaac Kennedy for the issue's centerfold, although she opted to keep the goods under wraps.

Vanity

Playboy

Prince protégée Vanity (of the group Vanity 6), née Denise Katrina Matthews, adorned the cover of Playboy's April 1988 issue. Ironically, the "Nasty Girl" singer and star of The Last Dragon became an evangelist in the 1990s, even pleading with Vanity 6 fans in her congregation to "keep praying for the Holy Spirit."  

LaToya Jackson

Getty Images/Playboy

Amid turmoil over leaving the Jackson family home and dropping her father Joe as her manager, LaToya Jackson turned to the pages of Playboy's March 1989 issue to declare her independence from her chart-topping brothers. The issue, which featured Jackson's topless centerfold, became one of Playboy's most popular, with around 8 million sold. Jackson returned to the magazine in November 1991, posing to promote her first autobiography; she also went on to act in a 1994 video for the magazine.

Traci Bingham

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Baywatch star Bingham first graced the cover of Playboy alongside her TV co-stars for the magazine's "Babes of Baywatch" edition in June 1998. The issue served as a tame follow-up to the magazine's Babes of Baywatch video, which came out a month earlier. Bingham has since been featured in the pages of Playboy more than five times.

Naomi Campbell

Getty Images/Playboy

In between assaulting her assistant with a phone and a rehab stint for cocaine addiction, Campbell posed nude for a spirited, Yuletide edition of Playboy in December 1999. The centerfold helped divert publicity away from the supermodel's troubles during the latter part of the 1990s.

Shari Belafonte

Getty Images/Playboy

The daughter of entertainer and activist Harry Belafonte, Shari posed nude for Playboy's September 2000 issue at the prime age of 46 — almost 20 years after she starred in the 1980s Aaron Spelling-produced TV drama Hotel.

LisaRaye McCoy

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Single Ladies starlet McCoy may seem like a shoe-in for Playboy, considering her cardinal role as stripper Diamond in Ice Cube's 1998 film The Players Club, but she only posed once for Playboy, in a small February 2004 pictorial.

Vivica A. Fox

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Fox took time out of her busy schedule as FBI Agent Nicole Scott on the Lifetime TV series Missing to pose for her modest spread in Playboy's October 2004 issue, a year after her noted role in Kill Bill, Vol. 1.

Stacey Dash

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She may now be part of VH1's trio of Single Ladies, but any child of the '90s remembers her as Dionne Davenport, and that's just what Playboy was going for when it featured Clueless actress Dash in its August 2006 issue. Dash gave Playboy readers a peek at her more "adult" side, posing nude for a five-page spread at the impressive age of 40.

Mariah Carey

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On the heels of The Emancipation of Mimi, Carey covered Playboy's March 2007 issue in a gilded one-piece, shedding her tame Glitter persona for an image more akin to the sultry, adult tracks of Mimi. While Carey may seldom turn down a cover shoot, a diva must maintain a bit of virtue — she chose to stay clothed.

Garcelle Beauvais

Getty Images/Playboy

Best known for starring alongside Jamie Foxx on his eponymous '90s sitcom, Beauvais bared it all for Playboy's August 2007 issue, six years after her stint as Fancy on The Jamie Foxx Show ended. No word on Beauvais' impetus for doing the shoot — except to show off a rocking 40-year-old body.