Celebrity Nude Photo Scandals

He’s been photographed half-naked, mooning the camera, and dressed in drag. Tom Sykes on why Kate Middleton’s little brother has the palace wringing their hands

Pippa Middleton

It turns out both of the Middleton siblings have had scandalous pasts. A day after the release of James Middleton’s alleged nude photos, a racy picture has emerged of Kate Middleton’s sister, Pippa. The picture shows the 27-year-old dancing in a purple bra and a skirt, next to a man in boxers. Pippa, who was the maid of honor at the Royal Wedding (and who also stunned in an Alexander McQueen dress) was largely seen as the ceremony’s “other star.” Pippa is said to be dating a former British cricket player, Alex Loudon.

James Middleton

Less than a week after Kate Middleton wowed the world with her grace as she became the regal wife of Prince William, her younger brother has emerged as a royal pain in her family’s bum. Pippa Middleton’s body-hugging maid-of-honor gown had everyone’s attention, but the Middleton girls’ brother, James, outdid his sisters with a nude photo leak. Pictures of him in his boxer briefs, mooning the camera, and in drag, and even one of him seemingly touching the family jewels popped up on Fleshbot (NSFW) this week. Though the images of James (allegedly from 2008) in various states of undress were previously floating around, they are getting more attention with all eyes on his family. The 24-year-old James is clearly the wild one of the Middleton children—he dropped out of Edinburgh University in Scotland during his first year, and though he cleaned up nice at the wedding to read inside Westminster Abbey, the world is now seeing a new side of James.

Charles Sykes / AP Photo

Jessica Alba

In the same month she graced the cover of Elle magazine telling readers that she's " shy," nude photos of a very pregnant Jessica Alba canoodling with husband Cash Warren surfaced on the website Fleshbot. Though the images show her bare breasts, Fleshbot editor Lux Alptraum says they're not all that racy. "I think Jessica's are just pregnancy pictures, not inherently sexual. These pictures are sweet."

Matt Sayles / AP Photo

Kat Dennings

Before saucy nude shots of Kat Dennings surfaced online, the 24-year-old actress was best known for playing opposite Michael Cera in Nick and Nora's Infinite Playlist. Then Perez Hilton blasted the pictures, reportedly taken with a cellphone, on his gossip website. Dennings hasn't commented on the matter, but a notice on Hilton's website confirms that they're real—Dennings' lawyers made him take them down.

Chris Pizzello / AP Photo

Kanye West

Anyone surprised by leaked photos of Kanye West clearly hasn't listened to his latest song. West, who quickly owned up to the spilled crotch shots, pointed to the first lyric of his latest song "Runaway" as evidence: "I sent this girl a picture of my dick," he raps in the song. His only regret about the pictures? "You cannot imagine how disappointed I was that I got cut off."

Andy King / AP Photo

Brett Favre

Legendary quarterback Brett Favre, who has been married since 1996, betrayed his wholesome persona while trying to win over 26-year-old Jenn Sterger, a model who worked with his then-team, the Jets. After repeated failed attempts at getting her attention by leaving increasingly desperate-sounding voicemails, the record holder for most consecutive starts refused to throw in the towel. Rather, he threw it off, reportedly texting her several pictures of his penis.

Chris Pizzello / AP Photo

Vanessa Hudgens

Hudgens, best known for wholesome Disney fare like High School Musical, has twice seen private nude images of herself leaked online. In 2007, Hudgens apologized to her fans for several risqué shots that had surfaced online, saying she was " embarrassed over this situation." Two years later, more topless pictures emerged—snapped by Hudgens herself—and the actress' lawyers quickly had them taken down. The young actress later told Allure magazine, "It's screwed up that someone screwed me over like that."

Scott Harrison / Retna Ltd.

Pete Wentz

Years before he became a father and Ashlee Simpson's husband, Fall Out Boy rocker Pete Wentz texted some crotch shots to a lady friend—but, of course, they ended up in the hands of a celebrity gossip blogger. Wentz admitted to sending them, writing that although it was " very upsetting," he was soon "ready to get back to laughing." Wentz later spoofed the ordeal in a Fall Out Boy music video.

Chris Pizzello / AP Photo

Ashley Greene

The 24-year-old actress, who plays clairvoyant vampire Alice Cullen in the Twilight films, was just a minor character in the series' first entry. However, when nude pictures leaked in August 2009, it seemed to have upped her profile considerably. Since then, Greene's Alice has figured far more prominently in the Twilight films, the actress herself has been seen on the arms of Chace Crawford and most recently Joe Jonas, and she's been cast in a series of big Hollywood roles, including opposite Hugh Jackman and Jennifer Garner in the upcoming film Butter. The pictures were reportedly leaked illegally and were taken down after Greene's lawyer threatened legal action.

Lefteris Pitarakis / AP Photo

Rihanna

2009 was a nightmare for Rihanna. In February 2009, then-boyfriend Chris Brown allegedly beat, choked, and threatened to kill her. Then, in May 2009, Perez Hilton posted a series of nude photos of her online. In an interview with New York City radio station Hot 97, the singer admitted she was the person in the photos. "They were for my boyfriend at the time," said Rihanna, adding, "if you don't send your boyfriend naked pictures, then I feel bad for him." She was, however, incredibly embarrassed by the incident. "It was humiliating and it was embarrassing—especially my mom having to see that," she said.

Chris Pizzello / AP Photo

Miley Cyrus

Miley Cyrus is no stranger to controversy. At 15, the Hannah Montana actress was first mired in a photo scandal back in January 2008, when the then-15-year-old actress posted pictures of herself in underwear on her MySpace page. Then, Cyrus posed in a controversial Vanity Fair photo shoot for Annie Leibovitz. Finally, in June 2010, gossip blogger Perez Hilton Tweeted an upskirt photo of Cyrus reportedly exiting a car sans underwear. Since Cyrus was only 17, Hilton narrowly avoided child-pornography charges.

Matt Sayles / AP Photo

Soulja Boy

DeAndre Cortez Way—now the Grammy-nominated artist Soulja Boy, known for his smash hit "Crank That"—was in hot water back in September 2008, when rumors on the Internet started appearing alleging that the rapper was the star of a gay sex tape. Stills from the tape of the singer receiving a blowjob from another man leaked, but were later proven to be fake. Then, in July 2009, Soulja Boy took to his Twitter, saying, "Question of the day. With me improving my music & hustle everyday how long before Soulja Boy becomes the next best rapper?" to which he attached a picture of him in his underwear. When his Twitter followers began mocking him for his lack of bulge, the rapper proceeded to stuff his underwear.

AP Photo

Jamie Foxx

A nude photo of Jamie Foxx leaked in August 2009. The actor later confirmed it was him. "What happened was, is that we were doing Miami Vice and I had to do a nude scene in Miami Vice," he explained. "So my makeup artist wanted to see the before-and-after, meaning, like, my body wasn't in shape and then we got it to that point, we wanna… but in transferring that material, I guess these people hang out on your Internet whatever, and they grabbed the picture and put it out there. So I apologize to my family."

Frederick M. Brown / Getty Images

Chelsea Handler

Never one to be tight-lipped, the host of last year's MTV VMAs was almost left speechless when Radar Online released stills from an alleged decade-old sex tape between the comedienne and an unknown British man. The tape begins with Handler in a standup comedy routine, and then quickly cuts to her having sex. Handler claims the tape was just a big, fat joke, reported the New York Daily News. "I would like to say to Radar Online, thanks for ruining my surprise Christmas gift to my staff," joked Handler. "No. 2, it was made as a joke. I put it on an audition tape for a comedy club, because I'm a comedienne, and I've been showing it at birthday parties for fucking years!"

Evan Agostini / AP Photo

Dustin Lance Black

"This is cold!" wrote gossip blogger Perez Hilton of someone's decision to sell pictures of Milk screenwriter Dustin Lance Black having unprotected sex, before posting them on his site. For Black, a gay-rights activist and safe-sex advocate, the most scandalous thing about the photos was that the sex was unprotected, something he was quick to address in a statement to " E!". "More important than the embarrassment of this incident is the misleading message these images send. I apologize and cannot emphasize enough the importance of responsible sexual practices." Black went on to sue the publication that bought the photos and the man he claims stole them.