Transvestite Celebrities
Contest Directions: What politicians or celebrities could possibly lose a bet and be forced to dress as transvestite - member of the opposite gender? Show us their humiliating moment of defeat.
This gallery only contains our top 16 selections from its parent contest Transvestite Celebrities. All 16 contest pictures can be viewed here.
  • Colin Powell

    Colin Powell
  • Rudy Guiliani

    Rudy Guiliani
  • Drew Carey

    Drew Carey
  • Hillary

  • Pee Wee

    Pee Wee
  • George Clooney

    George Clooney
  • Dr Phil Good

    Dr Phil Good
  • Charlie Sheen

    Charlie Sheen
  • Keith Richards

    Keith Richards
  • Danielle

  • Tony Blair

    Tony Blair
  • Dave Grohl

    Dave Grohl
  • Nick

  • Tom Cruise

    Tom Cruise
  • Osama

  • Chertoff

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This contest is fueled by the following news: In a recent Skins Game first, Fred Funk played a hole worth a whopping $75,000 wearing a pink flowered skirt. The attire was his penalty for being outdriven by Annika Sorenstam. In the end, the 49 year old Funk did have the last laugh, rolling a 15 foot eagle putt from the fringe on the ninth hole to win $225,000 and six skins. After coming close on the first two holes on the course, Sorenstam passed Funk by seven yards on the third hole. It was then that she pulled the skirt out of her bag. Funk agreed to wear the skirt for the entire hole if Sorenstam outdrove him. He maintained that he did not imagine he would have to wear the outfit so early on, however. Being a good sport, he put the skirt on over his pants and played onward. Sorenstam ended up signing the skirt while Funk was still wearing the garment. At one point, Funk asked Tiger Woods what he thought of the skirt. In the end, Woods' response was better suited to the locker room than anywhere else.

Contest Options

Contest Info

  • Started: 11/27/2005 06:00
  • Ended: 11/29/2005 06:00
  • Level: advanced
  • Entries: 16
  • Jackpot:
  • FN Advanced 1st Place $5
  • FN Advanced 2nd Place $3
  • FN Advanced 3rd Place $2
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