Crossdressing movies which is your favorite

Kinky Boots

"Ed Wood"

Fun, crazy movie. The main character, played by Johnny Deep, very accurately describes the obsessive, wonderful joy of crossdressing.

Hey Girls, It's Halloween and one of my fav ( showing my timeless beauty ), " Rocky Horror Picture Show " Classic evening fun dressed. Go all out with matching bra & panties with a guarder belt. Have fun  

I also loved The Danish Girl. Another favorite is Mascara. I'm going to look for The New Girlfriend and see if I can watch it.

Hi Cheryl havent seen either of them but will look  thank you..

Stephanie

Maybe I missed it but nobody loves RuPauls Drag Race? I’ve never seen it just because it seems so over the top cliche. Does anyone here know much about it? Worth a look?

GP

There was that niche British film I can't recall the title. It was about a young siblings that take loan from some young loan shark, and he gets engaged in a very strange abusive relationship with the boy, whom he encourages to crossdress and confuses him about who he really is.

If someone can recall this movie, please let me know as I'd happily watch it again. 

As for some classics there is a Polish TV series "Zmiennicy" from the 1980's. It's a completely absurd comedy, picking on the realities of everyday life of communist Poland, but the main plot revolves about the fact that a girl assumed an identity of a boy as she needed a job as a taxi driver and the company refused to employ her as a moment. Her second shift driver falls in love with her, which, obviously, results in a lot of complication. 

I watched it with some of my British friends and while they were not getting references as to Polish culture and living under communist rule, they loved it as a purely absurd monty-pythonesque feel. 

There is also an old Polish comedy classics "Sexmission". It's about two guys who agree to get hibernated for the science experiment, and when they are unfrozen, they found themselves in a totalitarian state and are though to be the only males in the whole world. I won't spoil it, but let's say it turns out they aren't. Some of the elements of the movie would be very politically incorrect nowadays, but it's still a cult classic and quite funny. 

I've got one that NOBODY will come up with! 🙃  In the James Bond movie, "Thunderball", it opens with 007 attending the funeral of a Russian spy. The spy's wife and children are there, with the widow attired in the traditional black mourning, including a hat with a veil. Somehow, 007 smells a rat, trails the grieving widow home, and get in a battle to the death with the widow...who's not really the widow but actually the supposed "late" spy. Seems he was trying to make agencies believe he was dead so they'd stop looking for him, freeing him up to make more global mischief. I was too young at the time to grasp what was going on, but now, after reading a few spy novels, I'm able to interpret what I saw... (If you search "Thunderball opening fight" on YouTube...)

I'm surprised that I don't see any mention a British move ,  Hit & Miss , about a Hit man but really a Hit Woman , who is a Transgender woman,  very well done !!!

Stephanie👠

Here’s one I just recalled due to this thread. The Silent Partner. Starred Elliot Gould and Christopher Plummer. Nice little bank caper flick from 1978. A good movie to begin with that throws in some crossdressing too. There’s a real young John Candy in it and lovely Susannah York looking very ‘70’s sexy as well. It’s also a ‘sorta Christmas movie’ too.

Jeff Bridges in ‘Thunderbolt and Lightfoot” springs to mind as well, come to think of it. That scene of him in drag climbing through a window like a man….Eek! Another great movie though.🥰

Does anyone recall that in the early 2000's, maybe '04, there was a show where maybe six or eight guys would crossdress and each week one would be asked to exit the show. The final episode left one CDer standing and would have to serve dinner to the entire family en femme. It was on network TV. 

I've been meaning to add in a mention for this one for a little while - Pretty Red Dress (2022).  It's a small-scale British film, but stars Alexandra Burke, whom UK girls at least should know from the music sphere, in her film debut.  I think she makes a very good job of it, even if she's not exactly cast against type.  Her Tina Turner cover, quite central to the plot, is superb.  It doesn't hurt that she's drop-dead gorgeous, either 🙂   But it's her boyfriend who is the reason for the CD interest.  His portrayal of the conflict between his very masculine South London street-life and the calling of his inner girl is quite relatable.  He can walk the walk, too.  It was shown on BBC2 at the end of February, and UK girls can stream it on the BBC iPlayer until the same point in 2026.

I liked the movie Too Wong Fu.  Seeing Patrick Swasey in drag was a hoot.

Hi All, I was surprised no one mentioned Will and Harper! It's a documentary, and it is more about coming to terms with transitioning MTF but it addresses a lot of the stress and question many of us face regarding our "hobby" or attraction to our femme side. It came out in 2024 and is on Netflix for sure. There were some very thought provoking scenes for me.....

Thanks, Steph, for inspiring this discussion

Maybe it's already been listed by I really enjoyed:

Ed Wood

Entertaining and the main actor describes his need to crossdress in an accurate and compassionate way.