Hollywood’s leading ladies (and even a couple leading men) have cashed in on their celebrity by posing for adult magazines, including Playboy. Actually, Playboy is the most iconic and best-paying magazine to pose for, but lots of stars have found success posing for other magazines, including Playgirl and Penthouse. Most of these stars understood that showing a bit of skin could make you a household name, and played up their good looks for that career boost.
Unfortunately, not all the stars on this list wanted their photos published. There are a few that didn’t. Some never intended their nude photos to see the light of day, but they’d already signed over their rights to the photographers who bought and sold them. That’s a price some stars are forced to pay when they pose nude before they’re famous and never expect anyone to find out. Such celebrities includes Brad Pitt and Madonna, both of whom dealt with the scandal in different ways.
The draw for adult industry magazines to publish celebrity nudes is obvious. Celebs draw buyers because who wouldn’t want to see Charlize Theron naked, or the very handsome David Duchovny covered by nothing more than a teacup? In fact, the list even includes two of America’s first ladies, our current first lady and Jackie O.
It’s a daring thing to lay it all out there, and these celebs cast aside their fears, and went naked for notable adult magazines. They dared to show it all for the other industry, and for that we thank them.
15. Jessica Biel – Gear (2000)
Back in 2000, Jessica Biel posed topless for the now defunct men’s magazine, Gear. Arguably, the photoshoot was inappropriate because Biel was only seventeen at the time, and her on-screen dad certainly had something to say about the resulting photos.
7th Heaven dad, Stephen Collins, told the NY Daily News that the shoot was “child p——–y.” He slammed and shamed Biel, even going as far as to suggest that her photographs would poison his own child. “I don’t want my kid to get the message that that’s okay.”
Yeah, Collins, may seem outspoken to a fault, but there’s something about this whole story that raises eyebrows. In 2014, Collins admitted to raping underage girls. His marriage counseling sessions were even recorded by his ex-wife, and those recordings were released. In them, he admitted to exposing himself to girls between the ages of 10 and 13. That makes his comments about Jessica more than a bit self-righteous and hypocritical, don’t you think?
14. Jaime Pressly – Ultra (2006), FHM (2005), Playboy (2004 and 1998), and Gear (2000)
Jaime Pressly has had an illustrious career. The beautiful blonde has had supporting roles on some notable films including, Joe Dirt and Not Another Teen Movie. She also became a household name with roles on popular television shows, including My Name is Earl, Raising Hope, and Two and a Half Men. She currently plays Jill Kendall on the television series, Mom.
Pressly loves to strip down. She’s been naked in countless magazines and is often filmed in her skivvies. She’s definitely not shy, and her willingness to take it all off hasn’t hurt her career. As for her nude spreads in Maxim and FHM, they allowed her to earn coveted spots on their annual lists. She was #87 in FHM’s “100 Sexiest Women in the World 2005” and #30 in Maxim’s “Hot 100 in 2002.”
13. Alyssa Milano – Newlook (1998), King (1994), Bikini Magazine (1993)
Alyssa Milano may not be working too much right now, but she’s still A-list. She’s starred in a number of popular television shows, including Who’s the Boss?, Charmed, and Mistresses. She was every man’s dream girl-next-door in the early 1990s, and she was even more desired after her spreads in Newlook and Bikini Magazine. Milano was unafraid to take it all off.
She’s always had a great body, even now, but Milano has this unshakable good girl image. Perhaps that’s why she stripped down for French girly magazines rather than Playboy, or other American staples of the time. Maybe she wanted to be seen as more womanly and artistic through the steamy and sexy photos — most of them are taken on a beach with Alyssa in little to no clothing.
Milano is still very beautiful. As recent as 2013, she stripped down for Maxim magazine. She didn’t quite bare it all, but she was still hot in little more than an unbuttoned flannel top. She looks great in her forties and proves you can be sexy at any age.
12. Angelina Jolie – Loaded (2000)
Back in 2000, Angelina Jolie wasn’t a “modern day saint.” She wasn’t a director, a humanitarian. She wasn’t married (or previously married) to Brad Pit, and she didn’t have six children of varying ages. Back then, she was a 25-year-old bad girl willing to get naked in a hotel room to discuss her role in the Lara Croft franchise. Jolie was arguably a lot more fun back in the day when she admitted installing a firepole in her bedroom so she didn’t have to take the stairs to get to the kitchen.
As far as sex goes, Jolie was never sexier than the late ‘90s/early ‘00s. She told the Loaded interviewer, “I just don’t see sex as this dirty, horrible thing – I see it as a connection with another human being.” She also admits to finding “everybody attractive,” so while you may have thought you don’t stand a chance with Jolie, you might actually do. Now that she’s ended things with Brad Pitt, what’s stopping you from heading to France to find out if she’s telling the truth?
11. Charlize Theron – Playboy (1999)
Long before Charlize Theron was an A-list actress, she was a fledgling model living from paycheck-to-paycheck. She sold some nude photos to get by. Eventually, she found herself in some top-grossing films. By 1999, she’d starred in The Devil’s Advocate with Keanu Reeves and Al Pacino, The Cider House Rules with Tobey Maguire, and That Thing You Do! with Tom Hanks. She also found herself unceremoniously unclothed on the cover of Playboy.
That was an achievement she wasn’t so proud of. Just when her career began taking off, Playboy was shrewd enough to publish nudes that she’d sold early on. Convinced the nude photos would hurt her career, Theron sued Playboy, but she lost the lawsuit and couldn’t stop the photos from running.
Fortunately for Charlize, the Playboy spread didn’t hurt her career whatsoever. She even went on to win an Academy Award for Best Actress for her role in 2004’s Monster. Since then, she’s starred in a number of films and became a household name.
10. Kim Kardashian – Playboy (2007) and Love (2015)
Kim Kardashian is no stranger to stripping down. She’s posed nude many times, and she’s even the star of a popular celebrity sex tape. Her body has certainly opened some doors for her, including landing her the starring role in E!’s most popular reality show, Keeping Up With The Kardashians. From KUWTK to small bits in movies and the covers of popular magazines, Kim K. has certainly made it to the A-list.
Rising to the top hasn’t stopped Kim from posing nude. Since her 2007 Playboy spread, she’s stripped down for Kanye’s music videos, Selfish (her debut book), Love magazine, and Paper magazine, just to name a few, but if you haven’t seen her Love magazine spread, it features Kim K. in full-frontal with “nothing but Prada.”
Kim has even posed naked while pregnant. Actually, people were criticizing her that she wasn’t actually pregnant and was faking the whole thing, so she posed nude to prove them wrong. She’s not at all afraid of baring it all, so expect even more nakedness from Kim K in the future.
9. Drew Barrymore – Playboy (1995)
At 19 years old, Drew Barrymore’s career was on the rise. She’d started acting ten years prior and was well-known for her roles in E.T. the Extra-Terrestrial and Firestarter. She grew up fast and beautiful, and had several roles in forgettable films where she played the girl next door. It wasn’t until 1992’s Poison Ivy that fans learned she had a tough, sexy side.
She dared to bare it all in Playboy and made the cover. The photo spread is a mockery of her formerly youthful image. She sheds this image in a series of pixie-like poses, most of which show off some perfect parts of her body. Following her Playboy spread, Barrymore found herself the star of basically every romantic comedy or sappy drama. Although the magazine didn’t launch her career, it certainly helped her get the attention she needed to catapult her career from the B-list to the A-list.
8. Cameron Diaz – Loaded Magazine (1999)
Cameron Diaz has a great body. She’s a surfer and healthy living advocate, and it shows in her lean, muscular frame. However, despite her incredible looks, she’s long shied away from fully nude photoshoots. One time though, way back in the halcyon days of her career, she posed nude for a photographer, and those pictures ended up being published in Loaded magazine.
She also once posed for a BDSM photoshoot, where she went nude in the photo set, but the pictures were never published to an adult men’s magazine. In fact, Diaz has had some luck in having those photos (and the accompanying video) suppressed. They’re very hard to find.
What’s not hard to find? Diaz’s topless photo shoot from Loaded, which shut down in March 2015 only to relaunch as a digital magazine just months later. Nevertheless, the stunning pictures of a Diaz in the water can still be found online. There’s an archive of Loaded spreads, and there are plenty of sites that republished the set of pictures.
7. Melania Trump – British GQ (2000) and Max Magazine (1997)
You may have seen Melania Trump’s nude photoshoot with British GQ magazine, in which she poses seductively on a fur-laden bed in a Boeing 727. In the various photos from the shoot, she wears handcuffs, diamond rings, and holds a pistol. She is entirely unclothed, except for a pair of stilettos, but she’s unashamed. The FLOTUS counts the photoshoot as “one of her greatest achievements.”
She is maybe not as proud of the photos she took for Max Magazine, as she refuses to discuss them in interviews. In the now-defunct French men’s magazine, she is photographed beside a woman. They’re snuggled together as if they’re about to get it on. The photos were reprinted in The New York Post with the headline, “Ménage A Trump.” In one of the photos, the other model poses to whip Melania, but the most revealing are when the two women are totally unclothed and in bed together.
6. David Duchovny – Playgirl (1997)
David Duchovny, star of The X-Files and Californication, once posed for Playgirl. He bared almost everything, showing his backside and even nearly going full-frontal. Only a teacup separates Duchovny’s manhood from full exposure.
Not a lot of A-list actors have the cojones to pose for adult women’s magazines, so good for Duchovny — despite some of his poses seeming a bit awkward. And it was even at the height of his career in 1997 that he bared it all. He didn’t need the money, but we’re certain the exposure didn’t hurt.
As for the accompanying interview, it tells a lot about Duchovny’s cool-as-a-cucumber personality. The actor actually has a B.A. from Princeton and an M.A. from Yale. He’s a smart guy, and even once taught as an English literature professor before switching to acting full time. His role in The X-files definitely paid more than his teaching gig, so it’s no big surprise he’s stuck it out in Hollywood.
5. Jackie Kennedy Onassis – Hustler (1971)
The most iconic photo of former first lady Jackie Kennedy Onassis is the one where she’s wearing her iconic pink and black suit and crying over the body of her slain husband in a stretch limousine. But for a brief time in 1971, it was Jackie O in her birthday suit that stole the attention of the entire world.
After she was widowed, Jackie Kennedy married Aristotle Onassis. She likely thought the rich shipping magnate would be a good husband because he’d been such a good friend to her following her husband’s death. Unfortunately for Jackie, Onassis turned out to be an asshole. He looked forward to any opportunity to humiliate her in the press. He even once went so far as to tattle that she’d be fully nude on a beach in Europe.
Hustler magazine purchased the rights to the photographs and published them without Jackie’s consent. Her sons were also bullied after the indiscretion, which actually doesn’t seem like such a bad thing now, but it was a different time back then. However, although Jackie was humiliated by the ordeal, she still signed a copy of the Hustler magazine for artist Andy Warhol.
4. Brad Pitt – Playgirl (1997)
Women aren’t the only ones who could find themselves in a nude photo scandal. Back in 1997, Brad Pitt was photographed naked in his hotel’s backyard. He was staying at a hotel in St. Barthelme, which is in the French West Indies, when a paparazzo snuck onto the private property and snapped the nude photos. Those photos were later sold to Playgirl.
Brad successfully sued the magazine, and Playgirl was forced to pull the magazines from store shelves. Brad was also awarded unspecified damages for both infliction of emotional distress and invasion of privacy.
It may seem strange that the judge ruled in Brad’s favor, considering that courts had ruled against both Charlize Theron and Jackie O in their lawsuits. However, Pitt couldn’t force the magazine to recall the copies they’d already sent to subscribers. Those magazines remain out there, which is why the photos can be quickly and easily found online, and they show everything.
3. Arnold Schwarzenegger – After Dark (1977)
Although After Dark magazine didn’t promote itself as a gay man’s magazine, it was very homoerotic. Arnold Schwarzenegger isn’t gay, but he did pose for the publication completely nude.
Today’s straight or gay male can pose for a number of erotic magazines without facing any backlash, but back in the ’70s, you could lose your entire career because homophobia and inequality were so rampant. It was a different, more difficult time, which makes Schwarzenegger’s nude photo spread that much cooler. He’s a big-time star now, but at that time, he was model, and this photoshoot was no big deal for him.
Coincidentally, the spread’s theme was “Musclebound for Glory.” And if anything was true of Schwarzenegger at that time, he was a muscular man bound for total glory. He’s the star of The Terminator, served two terms as California’s governor, and was the most recent host of The Celebrity Apprentice, although he has said he won’t be back on the show.
2. Olivia Wilde – Maxim (2009) and Flaunt (2012)
Olivia Wilde’s Flaunt photoshoot is incredibly risqué, but also beautiful and artistic. It comes with a message about what life is like today compared to pre-Internet days. Today, everything is online; every photo you take has the potential to come out. Rather than wait for someone to catch her naked in a place other than her choosing, Wilde bared it all in the daring photoshoot.
“It’s a strange time that we live in,” Wilde said when discussing the shoot. “Privacy is non-existent. Everything is permanent because of technology; there’s nothing that doesn’t stay around forever.” Lucky for us, these photos aren’t going anywhere either. There’s even an accompanying video on Flaunt’s website where you can watch Wilde strip down, pose, and be adored by the camera.
1. Madonna – Playboy (1985) and Penthouse (1985)
Back before Madonna was a superstar singer, she was a struggling performer. She needed the money, so she said “yes” when a photographer offered to pay her for amateurish nude photos. She was very natural in the nudes — meaning she didn’t shave her pits… or anywhere else for that matter.
Playboy and Penthouse eventually ended up buying and publishing those photos. Can you believe Madonna was paid only between $30 and $50 for the nude photo session? But both Playboy and Penthouse made a fortune off of them.
Instead of suing the publications, Madonna decided to own her sexuality and the fact that she had nude photos out there. Rolling Stone reports, “Both magazines greatly increased their print runs to satisfy demand, and Madonna refused to give in to the media frenzy and remained uncharacteristically mum. A New York Post headline at the time screamed, “Madonna: ‘I’m not ashamed.’” And why should she have been? She looked great.