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10 Rich Sportsmen Who’ve Dared to Dress in Drag

Sports
10 Rich Sportsmen Who’ve Dared to Dress in Drag

That a male is willing to dress up like a female says one of three possible things about him. It could be the case that the man is so supremely secure in his masculinity that he feels that putting on women’s clothing for a laugh or two doesn’t take away a shred of his manliness. It’s also possible that the man may be the type who’s willing to undergo embarrassment to be part of a group, such as for an initiation. Lastly, a man might dress up like a woman simply because he enjoys cross-dressing.

Whatever a male’s reasons are for dressing in drag is strictly his business; besides, cross-dressing is legal (in most places, at least). But the public shouldn’t be blamed if it can’t help but be fascinated at the sight of men wearing women’s clothing, more so if it’s a male athlete — the supposed stereotype of a “man’s man” — who’s in drag.

Here are ten rich sportsmen who, for one reason or another, have been photographed or filmed while cross-dressing:

10. Jo-Wilfried Tsonga / Tennis / Net Worth: $10 Million

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Because the ATP tour runs from January to December with practically no off-season, tennis players hardly ever catch a break from their profession. However, at the end of most tournaments, there’s usually a players’ party, where the athletes are given a chance to let go and enjoy themselves.

In 2011, the Monte Carlo players’ party was burlesque-themed, and ATP top-ten mainstay Jo-Wilfried Tsonga of France certainly took the theme to heart. Actually, we have former women’s World #1 Caroline Wozniacki to thank (or blame) since if she hadn’t posted the photo on Twitter, we would have never seen what Jo-Wil wore to the party.

Tsonga proudly sported a loud orange wig and a white bustier accessorized with a black feather boa. It’s certainly to Tsonga’s credit that he’s fully in character, seductive duck lips completing his look. Perhaps the only glaring fashion misstep Jo made is that he… uh… should’ve been more careful not to make it so evident to everyone that he’s really a man.

9. Blake Griffin / Basketball / Net Worth: $20 Million

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In 2008, The Lost Ogle posted three photographs of LA Clippers superstar dunker Blake Griffin frolicking through a field like a little girl while wearing a blonde wig, a pink halter top, and a green skirt. One of the pictures even featured Griffin embracing a man in semi-formal attire. The basketball world immediately went nuts over the photos as fans suspected that Blake actually enjoyed dressing in drag and hugging well-dressed men in open fields.

The website later revealed, however, that the pictures were of a 15-year-old Blake Griffin performing a skit in a back-to-school video for his high school, the Oklahoma Christian School (yes, Blake’s performance was for a Christian school production). So no, Blake doesn’t usually cross-dress, and he doesn’t randomly embrace well-dressed men either.

8. Charles Barkley / Basketball / Net Worth: $30 Million

Being the NBA’s Most Valuable Player in 1993, 6-foot-5 Charles Barkley may be the epitome of manliness. But he was perfectly fine with cross-dressing to promote his 2010 hosting gig for Saturday Night Live. More specifically, Barkley put on a black dress, a ponytailed wig, and hoop earrings to impersonate his co-host, Alicia Keys, as he lip-synched to Alicia’s smash hit, Empire State of Mind.

Apparently, Sir Charles enjoyed wearing a black dress and a wig so much that he donned them again for his 2012 commercial for Weight Watchers:

7. Eli Manning / American Football / Net Worth: $60 Million

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There must be something about Saturday Night Live that allows it to convince top male athletes to dress in drag. In 2012, the show got two-time Super Bowl champ and MVP (XLII, XLVI) Eli Manning of the New York Giants to put on a blonde wig, frosted lipstick, and a yellow gown with yellow feathers as he played Miss Chicken Fried Steak in a drag pageant skit.

One of the lines that Eli had to deliver for the skit was “I was good — I was damn good!” Uh… let’s just say that it’s fortunate that the younger of the Manning brothers only moonlights as a comedian and actually has American football as his main source of livelihood.

6. Dwayne Johnson / Professional Wrestling and American Football / Net Worth: $70 Million


During the 2009 Nickelodeon Kids Choice Awards, viewers voted that the show’s host should dress up like Miley Cyrus. That wouldn’t have been a very interesting gimmick, except the show was being hosted by none other than WWE superstar Dwayne “The Rock” Johnson. Needless to say, The Rock looked quite scary in a red off-shoulder mini-dress and a brown wavy wig.

In 2010, Johnson again dressed in drag, specifically in a pink tutu complete with size-14 ballet slippers, for the commercially successful but critically panned Tooth Fairy.

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5. Barry Bonds / Baseball / Net Worth: $80 Million

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In 2006, the San Francisco Giants put together an intimate gathering of fans and teammates to raise funds for the Giants Community Fund. The event, which was American Idol-themed, featured a mock contest where young players had to sing a song of their choice. And of course, for every competition, there has to be judges. That’s where Barry Bonds and his cross-dressing came in.

The career home-run record holder (726 home runs) gamely attempted to impersonate original Idol judge Paula Abdul as he put on a brown wig, dark shades, and a black strapless dress. Of course, Barry’s steroids-infused physique was a major obstacle preventing him from nailing the Abdul look. But his massive chest did give him some genuine cleavage to work with.

Well, at least Barry learned something from the experience. He shared, “I’ll never tell my wife to hurry up anymore because it took me forever to get ready. I’ll never do that again. I couldn’t get my hair right.”

4. Derek Jeter / Baseball / Net Worth: $185 Million

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So here’s yet another sportsman that Saturday Night Live was able to convince to cross-dress for a skit. The big difference here is that the athlete wasn’t at all painful to watch.

For his turn in drag in 2001, New York Yankees shortstop Derek Jeter hilariously played the wife of Yankees second baseman Alfonso Soriano. For his role, the now five-time World Series champion (1996, 1998-2000, 2009) sported a blue vest and a black skirt matched with a brown wig and gold earrings. One of the lines he hilariously delivered went, “I know I shouldn’t say this, but I think Tito Martinez is super foxy, girl.”

And as if one Yankee cross-dressing wasn’t enough, former pitchers David Cone and David Wells made appearances in drag as well.

3. Oscar De La Hoya / Boxing / Net Worth: $200 Million

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Unlike all the other athletes on this list who never denied their turn in drag, for years ten-time world champion Oscar De La Hoya refused to admit that the pictures showing him wearing a wig, fishnet stockings, and high heels were genuine. However, the Golden Boy eventually came clean in a 2011 Spanish-language interview where he admitted that he had been high on drugs and alcohol when the pictures were taken. Court documents also revealed that De La Hoya’s team had paid $20 million to silence Siberian model Milana Dravnel, who had taken the photos while the couple was still dating.

Oscar was so distraught when the infamous pictures went public that he thought about ending his life. Fortunately, De La Hoya, who started drinking at the age of nine, has been clean and sober for many years now.

2. Arnold Schwarzenegger / Bodybuilding / Net Worth: 300 Million

Austrian-born Arnold Schwarzenegger has worn many hats throughout his life, among them those of a three-time Mr. Universe titleholder, a top-grossing action star, a successful businessman, and a California governor. But Arnold, a cross-dresser? Yes, the Terminator has dressed in drag, specifically for the 1994 comedy Junior, where Arnold portrays a man who, in order to test the effectiveness of a new fertility drug, allows himself to be impregnated.

While granting an interview to promote the movie, Arnie shared how he felt about having to dress up as a woman for the role:

I loved it. I am as normal as anyone, but it is so much fun to see yourself with this make-up on. You know, what would you look like with the beautiful necklace hanging down?  Beautiful necklace — and around the wrists the bracelets, and the rings, and the diamonds sticking out. And also to try on different hairstyles, you know, the ones that soften your jawline. Ivan [the director] came in one day after we’d played around for three hours and said, “No, this is too much.” But I said, “No, Ivan, this is great. I’m really pretty now.”

1. Shaquille O’Neal / Basketball / Net Worth: $350 Million

Dressing up on halloween can be a lot of fun, and four-time NBA champion (2001-02, 2006) Shaquille O’Neal certainly didn’t want to miss out on the action in 2010. With girlfriend Nikki “Hoopz” Alexander dressed as a stout-bellied goon, “Shaqueeta” donned a brown bobbed wig, a diagonally striped blouse and a black skirt. In fact, the 7-foot-1 former center was even videotaped impressively lip-syncing and dancing to Beyonce‘s Sweet Dreams inside a parked vehicle he had been driving.

Shaqtin’ a Drag Queen, anyone?

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