Who are your favorite comedic crossdressers?

We’ve all seen comedy in crossdressing. Who are your favorites? You may pick 3. Have fun!

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  • Milton Berle
  • Jonathan Winters / Maud
  • Flip Wilson / Geraldine
  • Robin Williams / Mrs Doubtfire
  • Tony Curtis / Some Like It Hot
  • Jack Lemmon / Some Like It Hot
  • Dustin Hoffman / Tootsie
  • Dame Edna
  • Tyler Perry / Madea movies
  • Other - respond in chat
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    • #454860
      Araminta Purdy
      Lady
      Registered On: January 23, 2020
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      Not really a cross-dresser, as such, and, sadly, no longer with us. But Lady Chablis impressed me with her forthrightness, sometimes caustic frankness but mostly delightful insistence in being who she really was.

      Araminta.

    • #454853
      Grace Scarlett
      Baroness - Annual
      Registered On: February 16, 2021
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      Hi…

      Definitely the one and only…Eddie Izzard …manic, comic genius.

      Grace x

    • #453490
      Diana Morgan
      Lady
      Registered On: February 22, 2021
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      I love Eddie Izzard, he pleases himself as to which persona he projects and his portrayal of Darth Vader in the Death star cafeteria is a riot.

      1 user thanked author for this post.
    • #453210
      Elaine
      Duchess
      Registered On: September 2, 2015
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      Eddie Izard because he projects as a proud crossdressers.  Most of the others listed are a mockery.

      2 users thanked author for this post.
    • #453202
      Heather Harrison
      Lady
      Registered On: August 3, 2020
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      I voted for a stand up comic, instead of a movie character. I just love Eddie Izzard.

       

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    • #453191
      Brittney Andrews
      Lady
      Registered On: August 1, 2019
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      When I was a child, I’d seen and heard of Milton Berle and Dame Edna on night time comedy variety shows. But my favorite is a little unusual, Julie Andrews in “Victor, Victoria”. In the movie, she portrayed a female singer pretending to be a male singer crossdressing as a woman singer.

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    • #452697
      Sandy Jayson
      Duchess
      Registered On: September 29, 2019
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      I responded other I loved Tom Hanks in ‘Boosem Buddies’> my problem with all these characters is that they are either a character in a skit or a story of someone who needed to ‘hide out’. I would love to see a program of some one who wanted to be a crossdresser and dealing with those around her
      .
      Sandy

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    • #452665
      Millicent Teasedale
      Duchess
      Registered On: August 24, 2015
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      Add me to the Eddie Izzard fan club – especially for helping others – and me – own who I am and be proud of it.

      Then Tony Curtis and Jack Lemon – and especially the last line of Some Like it Hot – Nobody’s perfect!

      1 user thanked author for this post.
    • #452534
      Jamie Taal
      Lady
      Registered On: June 14, 2019
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      Tom Hanks in Bosom Buddies. Being a lost souled teen in the 80’s i was able to watch it easily on network TV and open the door to understand my repressed feelings.

      Fourth Grade Nothing: Bosom Buddies with Tom Hanks

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      • #452815
        Heather Megan
        Lady
        Registered On: May 15, 2020
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        I was only 5 or 6 when this was on, but I saw that and just remember thinking I wish I could dress that way and be seen as a girl too. Really my first memory of feeling like a girl on inside. Definitely a soft spot for BB. Thanks Jamie!

    • #452525
      Peggy Sue Williams
      Baroness - Annual
      Registered On: June 26, 2019
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      My memory might be a little fuzzy, but I remember going with my wife in January 1983 to see Tootsie, at a movie theater in San Angelo, Texas.  I was still in the Navy,  assigned temporary duty at Goodfellow AFB, attending a cryptology school.

      That movie was a must see for any CD, and Life magazine had done a detailed story on how Dustin Hoffman had to prepare for each day’s shooting of the film.  It was fascinating to see photos of him wearing all the proper female undergarments, beautiful clothing, shoes, getting made up by Hollywood experts, and finally seeing him appear as a very convincing looking female, as well as sounding like one.

      It was also frustrating for me, since I was not in any position to cross dress.  All our household goods, which contained my female wardrobe, were en route to Hawaii, which was my next permanent duty station.

      My supportive wife helped me make it through this stressful period, brought on by the stress of not being able to cross dress and the stress of attending a very difficult school.

       

       

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    • #452457
      Marti
      Baroness - Annual
      Registered On: February 5, 2019
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      … and another virtual vote for Saint Eddie Izzard, bless’ed be her name.

      Although my vote from those on the poll was Tony Curtis. He / she(?) played a great role in Some Like It Hot.

      Marti xxx

      3 users thanked author for this post.
    • #452366
      LisaT
      Lady
      Registered On: January 31, 2021
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      I have to love Eddie Izzard for being such an inspiration and role model. She empowers people to be themselves and be who they are not a stereotype  fitting societal norms albeit in a different way.

      3 users thanked author for this post.
    • #452327
      Camryn Occasionnel
      Duchess
      Registered On: December 10, 2018
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      My favorite entertainer/comedian crossdresser, based on looks alone, is actually Lilo Wanders. I’d burn 2 of my best wigs to look like her.

      2 users thanked author for this post.
      • #452544
        Victoria StJohn
        Lady
        Registered On: July 26, 2019
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        She is very pretty and feminine. Also, someone new to me. Thanks for sharing.

        1 user thanked author for this post.
    • #452169
      Rozalyne Richards
      Lady
      Registered On: March 10, 2018
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      Tony Curtis and Jack Lemon in Some Like It Hot has to be the best comedy C/D films ever x

      Hugs Rozalyne x

      1 user thanked author for this post.
    • #452101
      T.J. Byron
      Duchess
      Registered On: October 18, 2018
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      All of those folks are in my lifetime of viewing pleasure. All great folks , love them All, cause I love to Laugh!!

      Watched many as a kid in the 50’s on a 14″ B&W tube T.V.

      Later girls…

      Dr.  T J.

      • This reply was modified 6 days ago by T.J. Byron.
      • This reply was modified 6 days ago by T.J. Byron.
      2 users thanked author for this post.
    • #452087
      Jennifer Swanson
      Duchess
      Registered On: April 20, 2019
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      I just checked out Eddie Izzard on You Tube and she’s great!  First time I saw her.

       

      4 users thanked author for this post.
    • #452060
      Laura Lovett
      Lady
      Registered On: March 26, 2020
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      Eddie Izzard

      Love Laura

      5 users thanked author for this post.
      • #452300
        Heather Megan
        Lady
        Registered On: May 15, 2020
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        Eddie Izzard is fantastic, CD or otherwise. Saw him live (since he presented as male) and all her specials. Her book is a tremendous read as well, highly recommended.

        3 users thanked author for this post.
      • #452072
        IsabelB
        Duchess
        Registered On: March 18, 2019
        Topics: 3
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        Seconded, Laura

        She’s the best! 🙂

        Isabel x

        4 users thanked author for this post.
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