Unlike other pop stars who pose nude, Tiffany doesn't offer a convoluted explanation: She needed the attention.
The former teen sensation is hoping her 10-page Playboy pictorial will shatter her squeaky-clean image and get her back on TV and the radio.
"I did it to break down those barriers so people couldn't say, 'Aww, she's still 14,' and I also did it because I couldn't get booked on shows and it was a chance for me to say, 'Hey, if that phone rings, yes, it'll be because of Playboy, but I can talk about my music,'" she told ABCNEWS Radio.
"If they'll give me a shot, I can go out and do my thing, and I think it'll work."
'It Was Because of My Name'
The April issue of the men's magazine confirms that Tiffany has come a long way since 1987, when she sang to teenage girls in malls across the country and had a smash hit with a remake of "I Think We're Alone Now."
Now 30, Tiffany is a married mom. Her latest album, The Color of Silence, released in 2000, got fine reviews. But she says she couldn't get airplay because she's still thought of as a little kid singing silly pop songs.
"It was because of my name," says Tiffany, whose last name, by the way, is Darwish.
So, how do you tell your 9-year-old son that you're in Playboy?
"I tried to handle it the best that I could, which was kind of hard," Tiffany says. "But I did pull other magazines like Vogue and Elle … and frankly there's semi-nudity in those magazines.
"So, you know, I tried to explain to him, 'It's kind of like this but a little bit more.' But I'm just going to take it one day at a time with him. It's not something we talk about on a daily basis and he hasn't seen any Polaroids and I won't show him the magazine."
'Yes, I Had Breast Implants'
Tiffany admits that it was hard — even for her — to get used to seeing herself naked.
"I think I was a little overwhelmed at first," she says. "I mean I have the Polaroids at home … But it's different to see them in a magazine, you know, especially when you are flipping through and you see all these girls and then you see me."
Later-day teen stars like Britney Spears play up their sex appeal with belly-baring outfits and provocative dance acts. But Tiffany never went that route.
"I knew I had a lot of girl fans because we'd talk about earrings and shoes and shopping and boys and stuff like that," she says. "But the guys were pretty low-key."
The guys started stepping forward years later, she says. "Now I go places and there are all these guys come up and go, 'Oh my gosh, I had your picture above my bed,' and 'You know you were hot' and I'm going, 'Where were you?' So I had no clue. I really didn't."
Don't be afraid to ask if Tiffany's had a little plastic surgery. She says there is no point concealing that she's had work done on her breasts.
"People were going to ask no matter what. So you can take one of two approaches," she says. "You can lie about it, [but] they're going to find the truth anyway because somebody is going to come out with it … or you could say, 'Yes, I had breast implants.'
"I didn't do it because of Playboy," she says. "I did it because I was a mom and you know I didn't enhance my breasts as far as getting then bigger. I just put them back the way they once were, so that's all I wanted. I mean, that's what I said to my doctor, 'Just make me the way I used to be, OK?'"
ABCNEWS Radio and Buck Wolf contributed to this report.