Flip Floppers: 10 Celebs That Changed Their Gender Preference Later in Life

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When you’re forced to pick between two appealing options, it can really place you between a rock and a hard place; generally the choice is between two places to eat or something else equally mundane, but in the case of a special few it means picking between men and women! Living a double life is difficult for Celebs since they are always in the public eye and trying to keep up a good image, but even with the media buzzing around every corner some have been able to keep their sexuality under wraps.

All things eventually surface, so rather than let their secrets be revealed some celebs have surprised us all and come clean about their hidden romances; these celebrity flip floppers have changed teams more than sports players, and shocked us by shacked up with both genders! Whether the celebs are bisexual, or they simply changed their mind about who they want to love, it caught us off guard all the same. But which celebs were the most surprising to see start dating the other sex? Here are the top 10 celebs which changed their mind, and swapped their gender preference later in life.

Julie Cypher

Julie-CypherJulie Cypher is a film director from Wichita, Kansas, who was married to actor Lou Diamond Phillips from 1987 to 1990, and during her marriage would end up meeting her future partner while working on a music video. After Cypher and Philips separated, she revealed that she was gay, and began a relationship with singer Melissa Etheridge that would last for a decade.

During her partnership with Etheridge, Cypher gave birth to two children: a daughter named Bailey Jean, and a son named Beckett; both of them would be fathered by the musician David Crosby. Eventually, during a therapy session, Julie would come to the conclusion that she was, in fact, “not gay,” which resulted in the couple splitting up in September of 2000. After her second break up, Cypher would marry again, but this time it would be to a man; Cypher and Matthew Hale have been married since 2004.

Anthony Perkins

Anthony-PerkinsDo you remember Norman Bates from the cinematic masterpiece, “Psycho?” The role of Bates was played to perfection by the rising star, Anthony Perkins. After such an early success, Perkins would proceed to earn an Academy Award nomination for his role in the film “Friendly Persuasion.” In August of 1973, Perkins would marry photographer Berinthia “Berry” Berenson (a fan of alliteration); they would have two sons: Oz Perkins, who would become an actor like his father, and the future musician Elvis Perkins.

Although he was married to a woman for the final 20 years of his life, Perkins had had several homosexual affairs during his long-standing relationship. Perkins would end up dying from AIDS related complications with pneumonia in September 12, 1992, and his wife would end up passing away during the 9/11 attacks just one day before the ninth anniversary of his passing.

Billie Jean King

Billie-Jean-KingDuring her glory days , Billie Jean King was the top ranked women’s tennis player in the entire world, winning an incredible 39 Grand Slam titles. King was also a part of one of the most memorable tennis matches of all-time when she went face-to-face with Bobby Riggs in the Battle of the Sexes in 1973 and won.

Billie Jean got married to Larry King (no relation to Larry King of “Larry King Live” fame) in Long Beach, California, in September of 1965. By 1968, Billie Jean, now Billie Jean King, would realize she was interested in women, and would begin a secret lesbian relationship with her secretary, Marilyn Barnett. King’s illicit affair would become public when Barnett filed a “palimony” suit against her in 1981, and she would divorce Larry King in 1987 after losing great personal wealth in the suit stemming from concealing her sexuality.

Wanda Sykes

Wanda-SykesWanda Sykes got her start as a standup comedian, and gained recognition in the late 1990s as a writer for “The Chris Rock Show.” Sykes would marry record producer Dave Hall in 1991, but would divorce him by 1998 in the beginning of her shift in sexuality. Sykes went on to have film and television success as an actress and publicly revealed she was gay at a same-sex marriage rally against Prop 8 in Las Vegas on November of 2008.

Sykes married her partner of two years, Alex Niedbalski, just a month before the rally; the couple had twins around this point as well, rounding out an extremely busy year. In October 25, 2008, Alex gave birth to fraternal twins: daughter Olivia Lou and a son, Lucas Claude. Sykes came out to her conservative parents at 40 years old, and after declining her wedding and spending a brief time apart, they finally would accept her and her children: uniting the whole family.

Oscar Wilde

Oscar-WildeOscar Wilde lived from 1854 to 1900 in the country of Ireland, and he is one of the most prominent writers of all-time. Wilde was a phenomenal playwright who’s theatrical creations are still on stage. Wilde knew that he was gay at a very young age, even being dragged into a prostitution ring when he was a teenager. He was married to Constance Lloyd from 1884 to 1898, but revealed his feelings to the public during the end of the marriage.

After Lloyd’s second pregnancy, it was said that his “marriage had begun to unravel… which left him physically repelled” and Wilde began seeing a young man named Robert Ross, in what was recorded as his first homosexual affair. Even after Wilde was imprisoned toward the end of his life, Ross stayed with him and was even present at his side for his death in November of 1900.

Anne Heche

Anne-HecheAnne Heche might not be the most memorable actress of all-time, but she was a name that was fairly long-lasting. Some of the notable work that Heche was involved in include “John Q” and “Volcano,” but it was her relationship to Ellen DeGeneres that made her a household name. The couple began dating in 1997 and they once even said they would get a civil union if it ever became legal in Vermont, where they resided at the time. However, Anne and Ellen broke up in 2000, and she has said that all of her other relationships after DeGeneres have been male.

Heche had previously been in homosexual relationships, but has since gone back to men such as Coley Laffoon, whom she had a son with and was married to until 2007. Heche is now with her former “Men in Trees” co-star James Tupper, and they have a son named Atlas Heche Tupper, who was born on March 7, 2009.

Little Richard

Little-RichardOne of the pioneers of rock and roll was Richard Penniman, who went by the stage name of Little Richard. Richard got his start in the 1950s and was a mainstay in music for decades; although his music was consistent, his sexuality was a winding road. Little Richard has said that he felt feminine as a child and was caught wearing his mother’s makeup on various occasions, which resulted in punishment by his father. During the early 50s, Richard appeared as a drag performer and began using makup regularly after being influenced by fellow musician, Billy Wright.

While Little Richard felt that being gay was “unnatural” and “contagious” midway through his life, he revealed to Penthouse Magazine in 1995 that he was gay, and that he always knew it. Still, the rock sensation tried to hide it during his career when he married Ernestine Campbell, and the two were together from 1959 to 1963. “Good Golly Miss Molly,” Richard sure knows how to keep life interesting.

Portia de Rossi

Portia-de-RossiNot a lot of people know that model and actress Portia de Rossi is actually from Australia. The actress is most known for her roles on the American TV shows “Ally McBeal” and “Arrested Development.” De Rossi was once married to Mel Metcalfe from 1996 to 1999, which started out as a plan to get a green card. After her divorce, de Rossi would begin dating singer Francesca Gregorini in a more secretive relationship. Not yet comfortable with her sexuality, de Rossi declined discussing her sexual orientation or her new affair publicly.

In 2004 she split with Gregorini, and Portia began dating the one and only Ellen DeGeneres, and shortly after (2005 to be exact) finally publicly talked about her sexual orientation; since then, she has been in a long term relationship with DeGeneres and they tied the knot in 2008. Portia would finally become a United States citizen in September of 2011 with her name legally changed to Portia Lee James DeGeneres: a beautiful name showcasing her acceptance of herself and her sexuality.

Elton John

Elton-JohnElton John is one of the most prominent musicians to ever walk this Earth, and has been performing for over 50 years, still selling out the biggest arenas and venues all over the planet. John was in many notable relationships with women during the early days of his career, and his first was with secretary Linda Woodrow in the late 1960s; he even mentioned her in the song “Someone Saved My Life Tonight.”

Elton John came out as bisexual in 1976 in an interview with Rolling Stone. The first speculation’s about Elton just being gay, came about during his 1984 marriage to Renate Blauel, where people believed it was a cover for his homosexuality. John would then come out as officially gay in 1988 after divorcing Blauel. Since then, John has been in a relationship with David Furnish, and the two were married in 2005.

Rock Hudson

Rock-HudsonOne of the biggest names in Hollywood during the 1950s and 1960s was Rock Hudson. Hudson was the leading man in many movies: such as “Magnificent Obsession” and “Giant.” In 1955, allegations of Hudson’s homosexuality were perpetuated when Confidential magazine threatened to publish a story on his secret homosexual life. Many colleagues during his career claimed that his gay sexual preference was well known throughout Hollywood. Fortunately for Hudson, his agent Henry Willson, kept his personal life out of the headlines, including preventing the Confidential exposé from being published.

Hudson was married to Willson’s secretary, Phyllis Gates, from 1955 to 1958. It’s believed by many, thanks to an article published by gay news magazine The Advocate, that Hudson and his wife were both gay and used their marriage to hide it from the public. The actor passed away in 1985 due to AIDS related illness, and his death had a tremendous impact on the visibility of AIDS and its funding of medical research.

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