A famous Olympian turned reality star, the brother of a princess and an A-list actor have all been caught in this gallery of High Heels, Lacy Bras & Fishnet Stockings: 20 Cross Dressing Scandals that Rocked Hollywood.
John Travolta: In 2012, the National Enquirer exposed the Hairspray star donning women’s clothing in real life! The shocking photos taken at a Los Angeles party in 1997 show Travolta wearing a blonde wig, white dress, brown belt, fur stole, earrings and a necklace. The actor also had piled on thick black eyeliner and pink lipstick. According to the Enquirer’s sources, the cross-dressing scandal humiliated his wife, actress Kelly Preston, who has endured years of gay rumors about Travolta.
Jeff Chandler: Screen legend Esther Williams shocked fans when she wrote in her 1999 autobiography, Million Dollar Mermaid, that her former boyfriend, the late actor Chandler, was a cross dresser. Recalling the evening she allegedly found Chandler in red wig and flowered chiffon dress, Williams wrote, "Here was my lover--a strong, manly figure by anyone's estimate--who had just been standing before me in high heels and a dress. This was no joke. He enjoyed that kind of thing." Williams said she then broke up with the Merrill’s Marauders star. Many friends and co-stars of Chandler, however, staunchly denied Williams’ claims (she died in 2013 this year at age 91).
Pope Benedict XVI
The Vatican: Did a gay sex and cross-dressing scandal “drag” Pope Benedict XVI out of the papacy? When Benedict ended his reign as Pope in 2013, sources claimed he resigned after receiving a secret dossier that included details about a network of gay priests in the Vatican. The priests were allegedly being blackmailed by a network of male prostitutes who worked at a sauna in Rome. The evidence reportedly included compromising photos and videos of the prelates—sometimes caught on film in drag!
Bradley Manning: The U.S. Army soldier who was convicted of leaking restricted documents to WikiLeaks was revealed to be a cross dresser who wears lipstick and a long-haired blond wig. During his court martial hearing, the Army released a photo of Manning in drag which the soldier had sent to a sergeant to explain his sexual identity issues. Manning said in a statement she had felt female since childhood and wanted to be known as Chelsea -- and get hormone replacement therapy to become a woman.
Piero Marrazzo: The President of Lazio, a region of Italy, Marrazzo was the victim of a blackmail attempt in 2009 after government security guards had footage showing him in a bedroom with a transvestite prostitute. Marrazzo, also a former journalist, admitted to the affair and resigned in disgrace. The hooker, known as “Brenda” was found burned to death in her Rome apartment in 2009.
J. Edgar Hoover
J. Edgar Hoover: For years, it’s been rumored that the hard-nosed FBI chief known for maintaining voluminous files on perceived wrongdoers was also a cross dresser! In 1993, Anthony Summers, in his book Official and Confidential: The Secret Life of J. Edgar Hoover, claimed that Hoover did not pursue Mafia leaders because they blackmailed him over his cross dressing and alleged homosexuality. Summers quoted a socialite as saying that in 1958, she was at a party at New York’s Plaza Hotel where Hoover appeared wearing a fluffy black dress with flounces and lace stockings and high heels, and a black curly wig.
Oscar De La Hoya
Oscar De La Hoya: In 2007, stripper Milana Dravnel photographed the boxer in a fishnet bodysuit, wig, high heels, and women’s panties. When she allegedly leaked the photos, De La Hoya at first said they were a Photoshop forgery. But in 2011, he admitted, “Let me tell you, yes, it was me. I’m tired of lying, lying to people, lying to myself.” De La Hoya said he was under the influence of cocaine and alcohol at the time the pictures were taken. Later, New York model Angelica Marie Cecora claimed during a party that De La Hoya “started to put my stuff on, my underwear. I had a skirt with me. He put that on. He was playing a woman, very feminine.”
Eric Brewer: Brewer, the mayor of East Cleveland, Ohio, was running for reelection in 2009 when photos surfaced on the internet of the politician in drag. He was seen decked out in garters and a bra and suggestively displaying his butt. Brewer, who blamed his challenger, Council President Gary Norton, for the photo leak (Norton denied it), lost the election. In 2013, Brewer launched a launched a new digital newspaper, The Cleveland Challenger.
Kelsey Grammer: The actor’s ex-wife, former The Real Housewives of Beverly Hills star Camille Grammer, caused a firestorm after she implied to Howard Stern that he’s a cross-dresser! When Stern asked her on his radio show if Kelsey enjoyed dressing up in lady clothes off-camera, she said coyly, “I didn’t say it.” Camille also laughed, “He has a little waist. I don’t know what to say.” In a 2012 interview, however, Kelsey said he has been "very sexually adventurous" during his life but has “never been a cross-dresser.”
Marv Albert: When the NBC broadcaster known as “the voice of basketball” went on trial for felony charges of forcible sodomy in 1997 against girlfriend Vanessa Perhach, another woman took the stand and said Albert was a cross dresser. The hotel employee testified that Albert called her to help him send a fax. But she said she arrived to find Albert wearing a garter belt and women’s underwear, and he tried to force himself on her. She escaped by fleeing the room. Albert pleaded guilty to misdemeanor assault and battery charges and was given a 12-month suspended sentence.
DJ Mister Cee
DJ Mister Cee: The prominent hip hop DJ resigned from New York's Hot 97 after 20 years with the radio station in 2013 after drag queen and video blogger Bimbo Winehouse posted an audio in which Mister Cee offered him money for sex. The DJ decided to leave the station. But he quickly resumed his job, admitting although he “loves women,” he occasionally gets “the urge to have oral sex with a transsexual, a man that looks like a woman.” Mister Cee had previously been busted in 2010 and 2011 after cops found him with cross-dressing prostitutes.
Anthony Weiner: The scandal-plagued New York Congressman resigned in 2011 after the National Enquirer published a shocking cover photo of him wearing women’s lingerie. The pictures, taken in 1983 when Weiner was 18, dated back to his college days at the State University of Plattsburgh. In one photo, Weiner smiled for the camera while wearing a bra and pantyhose. Within hours of publication, Weiner announced he had made the decision to give up his House seat and resign. He lost in the recent New York mayoral election.
Kevin Wallin: In 2013, the priest of St. Augustine Parish in Connecticut was indicted on charges of distributing crystal meth. Monsignor Kevin Wallin allegedly sold shipments of meth to undercover cops between September 2012 and January 2013. It was also claimed the priest dabbled in cross-dressing! A source told The Connecticut Post that rectory officials were aware that Wallin occasionally cross-dressed and engaged in sex acts with "odd-looking men," who also sometimes dressed in women's clothing.
Lee Tamahori: The Die Another Day director was caught allegedly dressed as a woman and trying to sell himself for sex to an undercover cop in Los Angeles in 2006. Police said he donned a black wig and a revealing, off-the-shoulder dress and wore makeup. But Tamahori was convicted only of criminal trespass, having pled no contest in exchange for other charges being dropped.
Richard Curtis: In 2007, Washington state cops released a report that said Republican Representative Richard Curtis dressed up in women's lingerie and met a man in a local erotic video store which led to consensual sex at a downtown hotel and a threat of blackmail. During his visit to the video store, Curtis was allegedly observed wearing the women's underwear while receiving oral sex from an unidentified man in one of the movie viewing booths inside the store. The married father promptly resigned, saying, “I sincerely apologize for any pain my actions may have caused.”
Ronaldo: Brazilian soccer star Ronaldo was caught in a sex scandal with three cross-dressing prostitutes in 2007. In Rio de Janeiro, the 2002 World Cup winner allegedly picked up three hookers. Once at a motel, the AC Milan striker discovered that the prostitutes were in fact men. According to Rio police, Ronaldo charged that the transvestites then tried to extort money from him. His wife dumped him, they later reconciled, but split again in 2012.
James Middleton: Photos of Kate Middleton’s brother in drag raised eyebrows when they were released in 2011. One picture showed a youthful James dressing in a French maid’s uniform while goofing around with friends and in another photo, the Duchess of Cambridge’s brother, who now runs a cake kit company, was shown wearing a tight black and white polka dot woman’s mini dress and grabbing his crotch.
Marvin Gaye Sr.
Marvin Gaye Sr.: The minister father of Marvin Gaye, who shot and killed his famous singer son in 1984, was a compulsive cross-dresser. According to the book Divided Soul: The Life of Marvin Gaye, his dad’s habit of dressing like a woman humiliated the What’s Going On singer. At the age of 12, he witnessed Gaye Sr. wearing his wife’s clothes. Gaye Sr. killed his son after Marvin and his parents got into a days-long argument over business. He pleaded no contest to a voluntary manslaughter charge and died of pneumonia in 1998.
Bruce Jenner and Ellen Kardashian
Bruce Jenner: During an interview, Robert Kardashian’s former wife Ellen claimed the Olympian was a cross dresser! In 2012, Ellen reportedly told how she learned about Bruce's habit during drinks with Bruce's ex-wife, Chrystie. Ellen claimed Chrystie told her, “I went on a trip and I came back and he had gone through all my clothes. And I found my bras…He’d clip them together and wear them. I couldn’t live with that." And in a recent Star magazine article, sources said Kris Jenner was preventing Bruce from divorcing her-- allegedly “threatening to expose Bruce as a cross-dresser if he tries to leave her!”
Robert Durst: In a bizarre case of a cross-dressing killer, wealthy real estate heir Robert Durst (whose wife Kathleen mysteriously disappeared in 1982), was arrested in 2002 for murdering his neighbor in Galveston, Texas — where he’d been living as a woman under a fake name. Durst was known as “Roberta” and was seen tottering around town in high heels, a dress, and a woman's wig. He went on trial in 2003 for shooting his neighbor in the face and chopping up his body but was acquitted of murder by jurors who believed it was self-defense. He’s recently been buying multi-million dollar properties in New York.