Who are your favorite comedic crossdressers?
We’ve all seen comedy in crossdressing. Who are your favorites? You may pick 3. Have fun!
- 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
- This topic has 21 replies, 20 voices, and was last updated 1 day ago by
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Registered On: January 23, 2020Topics: 4Replies: 284Has thanked: 408 timesBeen thanked: 972 timesNot 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.
- Registered On: August 1, 2019Topics: 3Replies: 659Has thanked: 41633 timesBeen thanked: 1281 times
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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- Registered On: September 29, 2019Topics: 17Replies: 390Has thanked: 811 timesBeen thanked: 1715 times
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
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- Registered On: August 24, 2015Topics: 11Replies: 176Has thanked: 37 timesBeen thanked: 335 times
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!
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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.
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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!
- Registered On: June 26, 2019Topics: 12Replies: 259Has thanked: 930 timesBeen thanked: 1123 times
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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- Registered On: February 5, 2019Topics: 11Replies: 114Has thanked: 494 timesBeen thanked: 479 times
… 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
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- Registered On: January 31, 2021Topics: 14Replies: 131Has thanked: 99 timesBeen thanked: 593 times
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.
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- Registered On: December 10, 2018Topics: 0Replies: 426Has thanked: 775 timesBeen thanked: 1098 times
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.
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She is very pretty and feminine. Also, someone new to me. Thanks for sharing.
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- Registered On: October 18, 2018Topics: 0Replies: 319Has thanked: 3116 timesBeen thanked: 1294 times
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.
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- Registered On: March 26, 2020Topics: 13Replies: 871Has thanked: 2791 timesBeen thanked: 4194 times
Eddie Izzard
Love Laura
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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.
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Seconded, Laura
She’s the best! 🙂
Isabel x
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