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7 Musicians in Playboy: Madonna, Mariah Carey, Azealia Banks and More

by Ryan Book   Jul 15, 2015 14:53 PM EDT

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Thirty years ago, pop fans-but mostly guys interested in the female form-received the most recent issue of Playboy, which featured superstar Madonna on the cover. Looking back, it doesn't seem all too surprising that perhaps the biggest female performer in history stripped down for the men's magazine...after all, she released a whole book of risqué content with Sex during 1992. But for the most part, Playboy has been an arena more enticing to film and television actresses, as well as other recognizable characters. Musicians have been more rare, but they drop in from time-to-time. So withhold your judgement and check out this safe-for-work array:

La Toya Jackson (1989)

One would think that being a member of the Jackson family would be enough publicity on its own, but La Toya thought otherwise. This was during an era where someone like Michael Jackson could become the biggest pop star of all time with nary a sexual suggestion. Maybe his sister wanted to take her music in a sexier direction, maybe she just saw it as a way to separate herself from her talented siblings, or maybe new manager Jack Gordon was bullying her into it (as the Jackson family has continued to claim). Either way, she appeared on the March 1989 cover and it was a hit, becoming the no. 14 bestselling issue in the magazine's history. Although she had clearly broken the family-friendly mold with the appearance, as well as singles such as "You're Gonna Get Rocked!" (don't make us explain it), she and the Reagan administration still got along: Her self-titled album released around that time also included the anti-drug "Just Say No," written for the conservative icon.

Nancy Sinatra (1995)

Musicians who write rather lascivious lyrics are frequently asked how they would feel if it was their daughters in another performer's lyrics. Although Frank Sinatra wasn't all that raunchy in his lyrics, there can be no doubt that he and the rest of the Rat Pack had access to nearly any woman on Earth in their primes. How Ol' Blue Eyes responded when daughter Nancy told him she'd be appearing on the cover of Playboy depends on who you ask: Some of the other family members claim he was in a rage, while Nancy herself says that he asked how much she was getting paid and then advising her to "double it." Most of the controversy that surrounded the shoot had nothing to do with morality however, as men everywhere whined that 54 was too old for someone to appear in the nude. To them we say: Get out of here. Sinatra was behind "These Boots Are Made For Walkin'," one of the sexiest songs of all time, and she kept herself in great shape, to boot.

Ginger Spice (1998)

There's occasionally the false belief that the women who appear in publications such as Playboy must be on-the-out. Geri "Ginger Spice" Halliwell of the Spice Girls (along with Madonna) are case-and-point that this is untrue. Spiceworld may not have been the chart-topping debut Spice, but it still peaked at no. 3 on the Billboard 200. Her appearance on the cover of Playboy's May 1998 issue came suspiciously close to her announcement on May 31 that she would be leaving the group due to depression. There's an argument however that she was attempting to build more of a profile in preparation for a solo career, as she released her personal debut If Only the next year. Of course, maybe Halliwell just bought into Madonna's belief that owning one's body was a feminist as it gets. After all, she did give her eldest daughter the middle name "Madonna."

Tiffany (2002)

Then again, sometimes the suggestion that women who appear in publications such as Playboy might be accurate. Tiffany broke onto the pop scene during 1987 with two no. 1 singles—"I Think We're Alone Now" and "Could've Been"—kind of turning her into a creepy sex symbol in the Britney Spears manner (we don't care what they do in the music video...grown men shouldn't get hot and bothered by high schoolers). Playboy was legally prohibited, of course, from featuring her at the time, but she would be legal at some point during 1990. Unfortunately, her career totally fell through from his freshman to sophomore albums. She explained at the the time of her cover shoot that she did it so listeners wouldn't perceive her as a teenage girl anymore, which makes sense...we suppose.

Debbie Gibson (2005)

If you think we're making assumptions about Playboy reaching out to pop stars as soon as they turn 18...you may or may not be correct. Debbie Gibson, who came up as Tiffany's "pop rival" during the late '80s reported that she had turned the magazine five times since she turned 18. Apparently the sixth time was the charm, as the songwriter finally went for it. Of course, it also played well into her current PR campaign, as she was about to release a single titled "Naked." Did it work? Maybe a bit. It definitely didn't get to no. 1 like "Foolish Beat," and it didn't even result in an accompanying album.

Mariah Carey (2007)

Right? Theoretically the bestselling issue of Playboy ever ended up being somewhat like the 50 Shades of Grey movie (for people who wanted a literal, word-for-word translation). Carey didn't actually reveal anything. She appeared in swimsuits and lingerie, but those who picked up the issue just for her could have saved some money and watched any number of music videos from her catalogue. It would have been perfect if the last page of the feature had a photo of then-boyfriend Nick Cannon with the caption "Punk'd!"

Azealia Banks (2015)

And, 30 years later we've come full circle. Madonna may have shown some skin during her cover shoot with Playboy but you can bet that there was an ulterior social media. Azealia Banks is outspoken to such a degree that she makes Madge almost seem withdrawn, but you can bet that both agree on one thing: Softcore pornography isn't exploitative unless you make it do. And few women have owned their interviews with the publication as Banks did. It's one of the few cases in the publication's history where we heard much more about the words than the picture. The emcee dropped bombs on her usual range of topics, from reparations for slavery to different standards being held for white and black performers. Hopefully someone actually read it.

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