Playboy Asked Debbie Gibson to Model 5 Times Before She Agreed

Bruce Glikas/FilmMagic

Videos by Rare

Videos by Rare

When 80s Pop Icon Debbie Gibson first made it big, she never thought that she’d one day be in Playboy. But after about 15 years of being asked to pose for the publication, she finally agreed in 2005. Gibson’s Playboy photoshoot had the biggest styling budget ever. Considering it was technically a “nude” photoshoot, that’s pretty amazing.

Playboy Asked Debbie Gibson to Model 5 Times Before She Agreed

“Playboy approached me for the first time when I was like, 18,” Debbie told Oprah: Where Are They Now? “It was like, ‘Ok, another girl turned 18, pick up the phone.’ And I was like, ‘I’m not even in high heels yet.’ So that was like, not even anything I entertained.”

After about five requests from Playboy over the years, Debbie finally agreed. She was about 32 years old and had just performed on Broadway as Sally Bowles in Cabaret. She felt that with the new sultry and sexy image that she was starting to carve for herself, doing Playboy felt “congruent.”

“I felt oddly excited by it, at home with it. I felt this sense of adventure about it. And they let me do it on my terms — to the point that they said they never had as big of a styling budget for a wardrobe in a nude photoshoot ever.”

Debbie Was Supposed to Be on Cover of March 2005 Playboy Issue — But Was on a Pullout Cover Instead

Debbie ended up posing for about 1,500 photos in total at the shoot. And while many of them showed her nipples and butt, she didn’t end up on the cover. The March 2005 Playboy issue featured Paris Hilton on the cover instead — although Hilton was full clothed as well. Debbie Gibson instead had a pullout cover.

“They said I didn’t show enough,” Gibson told Oprah. “Which I was thrilled with,” she added. Some international versions did feature Gibson on the cover, however. *See above.

Debbie Gibson’s career trajectory went from teenage sweetheart pop queen to skin-baring sexpot, but she somehow managed to always keep it classy. Maybe it’s because she waited until she was in her 30s and was acutely aware of her fanbase.

Speaking with E! News’ Giuliana Depandi prior to the release of the March 2005 Playboy issue, Debbie Gibson said that she wasn’t afraid to “offend” her fanbase. Because, as she’d grown up, so too had her fans.

“I don’t think what people think anymore,” Gibson told Depandi. “My fanbase — they’re not teenagers. They’re not 10 years old. They’re 30-something year-olds. And so, you know, I’m not afraid of offending them at this point.”

Debbie’s Playboy Pictorial Coincided With the Release of Her Single, “Naked”

The March 2005 Playboy issue’s release coincided with Debbie Gibson’s new single, “Naked.” Gibson told Fox that the song came first, but that there was a connecting theme with the Playboy shoot.

“I had been working on revamping the song. Just kind of the theme of the song and the theme in the shoot,” Gibson told Fox’s, Martha MacCallum. “I should say my reason for wanting to do the shoot is the same. It’s kind of like putting yourself out there and saying, ‘You know what? You can all think what you want. This is who I am.’”

Debbie added that while “Naked” is about vulnerability in a relationship, her choice to pose for Playboy mirrored that vulnerability. “This is me open and vulnerable to the cynical people in the world,” she said.

From Teen Queen to Seductress

Gibson also told Fox that when Playboy called to invite her once more to do a feature, the call actually went to her agent instead of her. She took that as Playboy not realizing that she was an adult who could make her own decisions. She said they “didn’t know that Debbie Gibson was an adult. I have been an adult for 15 years.” Debbie added that “I haven’t been a teenager in so long it sounds silly that I was a teenager.”

While Debbie had actually been to the Playboy Mansion three times before to perform songs at the piano for Hugh Hefner’s guests, modeling for the publication was entirely new. Indeed, she was no longer a teenager, but a stunning blonde bombshell with a contagious smile. And her Playboy shoot would solidify her new image.

The March 2005 Playboy cover said, “Teen Queen Debbie Gibson NUDE.” Paris Hilton is leaning back in a red satin balconette teddy and black fishnets. It’s very “Cabaret,” almost a reference to the photos of Debbie Gibson within the pages.

Debbie Gibson’s 2005 Playboy Pictorial


Full disclosure: We don’t have access to the original March 2005 Playboy magazine issue. The descriptions of Debbie Gibson’s photos below are how we found them online. It’s not clear if she showed as much skin in the original magazine as can be seen on the internet. While speaking with Fox and with E!, Gibson mentions and even shows photos with red ribbons covering parts of her body. Those may have been used just for promotional purposes but not in Playboy. It’s not clear.

It’s apparent why Debbie Gibson’s Playboy photoshoot had such a large budget. While lacking many clothes, she’s shown adorned in gorgeous and very expensive jewelry. Her first photo shows her wearing a sheer black underbust corset, matching thigh-high panty hose, garters, and heels. She’s leaning forward in a chair, using her arms to cover her breasts.

Two photos show her wearing nothing but a lime green jacket and diamond necklaces. One of those necklaces is draped around her neck and the other serves as pretend underwear. One angle shows her bare butt, with the necklace hanging across, and the other shows her from the front. The diamonds are placed as a perfect cover-up.

Another photo shows Debbie Gibson looking at herself in a mirror. Her blonde locks are curled and she’s holding them up with one hand. Her other hand is playfully touching her décolletage, which features multiple pearl necklaces of varying sizes. Debbie’s breasts are otherwise bare and very visible.

Another photo shows Debbie as Sally Bowles. She’s wearing a black bubikopf wig with bangs, black satin choker, and above-the-elbow black gloves with bangles. Fishnet thigh-highs complete the look as she’s holding a black fedora to cover herself below her waist.

Other photos show a completely nude Debbie Gibson lying down, with nothing but a hot pink plush stole. In some photos, the stole is strategically covering her breasts. In others, you can see everything and it’s more of a comfort item. One photo features Debbie completely naked but with a red stole and matching lipstick. She’s wearing a chunky diamond necklace and lying on satin sheets. You can see one of her bare breasts as she’s giving her huge smile and looking at the camera.

One thing is clear. Debbie Gibson oozes confidence. You’d never know that she was once a teenybopper icon when looking at her Playboy photos. Props to the pop queen.

Read More: Playboy Immediately Embraced Dorothy Stratten as a Lauded Playmate

What do you think?

Leave a Reply

Your email address will not be published. Required fields are marked *

What Happened to Matthew Garber from ‘Mary Poppins’?

What Happened to Charles ‘Tex’ Watson From the Manson Family?