Tiffany arrives at Children Uniting Nations' 9th annual awards celebration

Tiffany arrives at the Beverly Hilton hotel on February 24, 2008 in Beverly Hills, California. 

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Tiffany talks about her infamous 2002 Playboy shoot, and how it affected her career.

In an age of oversharing, naked pop stars aren’t unusual. Miley Cyrus, FKA Twigs, Lady Gaga and Selena Gomez have all stripped for high-end glossy V Magazine. But what’s rare about Billboard cover star Azealia BanksPlayboy shoot is that she’s an artist, presumably at a career peak, who posed completely nude without the pretext of fashion, but in the bold name of good old-fashioned sex.

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Before leaked images regularly turned up online or companies peddled stolen sex tapes, celebrity nudes were a vestige of a pre-fame modeling past (see Madonna’s art-school photos in the September 1985 issue of Playboy) or part of a calculated reinvention. In 1995, country-pop singer Nancy Sinatra graced the magazine’s cover at the age of 54, nearly 30 years after “These Boots Are Made for Walkin’” topped the charts. La Toya Jackson went topless for Playboy in 1989, ostensibly to distance herself from her family (and selling eight million magazine copies in the process). In 2002, former teen-pop star Tiffany posed totally nude in Hugh Hefner’s monthly as a bid for a second act. “More than about being naked, it was about being [seen as] a woman,” says Tiffany, now 43, who in her 30s was still defined by her adolescent mall concerts. “As soon as I posed, we couldn’t stop the phone from ringing — it worked.” (It worked so well that in 2005, her youth-pop contemporary Debbie Gibson also posed for Playboy.)

Playboy-Tiffany-April-2002

Courtesy of Playboy

Here Tiffany talks about what it was like to pose and how she'd do it all over again "in a heartbeat!"

Why did you decide to pose for Playboy?
For me, it was [that I was] still perceived like, "Oh, you’re that mall girl." [Laughs.] Which was really frustrating. Although I’m very proud of my success — how I started, all of that — but as a woman trying to bring new music to light that was really all anyone wanted to talk about: "What’s the mall’s been like? Did you like the mall?" And I was like, "Really?" I came off that tour and all of a sudden I got the call from Playboy. I was going through a divorce — as a woman, I was like, "That is a great idea!"
 
How did it affect your career?
It was a confidence booster. I never thought that I’d be posing nude in Playboy to work my career or push my music. It seemed a little bizarre to me [at first], but when I’m 80 years old, I’m going to look back on these pictures and think, "Wow, that was really cool." But it definitely did work. A lot of TV shows that I’d been asking to do, my PR people were trying to get me on there for the new album [2000's The Color of Silence], and no bites — from The View to a lot of different shows. But as soon as I posed for Playboy, we couldn’t stop the phone ringing. It worked.

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What were the negative reactions like?
When you’re talking branding or representing somebody for a commercial, a lot of people don’t want to be associated [with nudity]. I’ve had that little bit of backlash, but for the most part it’s been very favorable. It’s always going to be there in my life. I love the pictures. It really opened up more of a male audience for me, which was really cool. More than it was being naked, it was about being a woman.
 
What was the experience of posing like?
It was wonderful. I couldn’t eat anything during the two days I was posing, but they’ll give you whatever you want to eat! I was like, "I don’t think I can" [Laughs.] But after, they throw you a big party.

Did you think about posing for Playboy when you were just starting your career?
Oh, no. I started out as a kid, I was only 15, so we couldn’t even talk about that. It was hard for my label and my management to figure out how to bridge that gap: How to make me a valid older teen, young adult, and be a little more sexy and flirty. There’s a fine line there. For me, I got frustrated at 18 and dyed my hair black and got my nose pierced! [Laughs.] I probably did it all wrong.

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What do you think about younger artists on the rise, these days, who decide to pose nude?
It’s a great honor to be asked to pose for Playboy. I do think that as a woman, it is your choice. As a career move, it definitely launches you into a different brand, it expands that brand. You’re not just a musician; you’re a sex symbol. Maybe with a band it’s different, but for women, the image is so important — what you wear, your hair — all of it.
 
Have any artists reached out for advice before posing themselves?
I usually meet the girls after: Carnie Wilson — we talked about how she posed — or Downtown Julie Brown. These are my friends. It’s funny that we all have that in common, the Playboy shoot. Everybody I know [who did it] thinks it was an amazing experience. They make you feel beautiful.
 
Would you do it again?
Yeah, I probably would do it again! I had a young son when I did it — some family members weren’t happy about it — but I was happy with it. Now, I’m 43 years old, I would do it again in a heartbeat! [Laughs.]

This story originally appeared in the April 11 issue of Billboard.