As promised, here’s part 2 of the previous discussion of “t-films” but it is by far the harder part to write. The problem? Some aspect of cross-dressing or drag queens have been included in an almost uncountable number of films. So the very first thing you have to do is sort out how much transgender content is enough to really qualify for the list.

Then there’s the matter of whether you consider movies which feature anon-transgender person forced by some circumstance (usually for comedic purposes) into a cross-gender presentation (think, “Some Like it Hot”) or whether you narrow the field further to only those plots which turn on an actual transgender character as a central axis. Doing so at least gets you down to a manageable list of candidates.

Further, for me at least, you can lay aside foreign language films as that is simply not my thing and I doubt I’ve ever watched even one all the way through.

Now having done this, I’ve excluded quite a number of comedies which I enjoyed, on some level, but just didn’t see how I could sort through them for a post like this. The aforementioned Some Like it Hot is, of course, the gold-standard as the most high profile and “big ticket” example, usually the trope is found in much more low-brow fare. For instance, the Tim Daley/Sean young film “Dr. Jekyll and Ms Hyde” – there’s nothing classy about that but on some basic level, I was still drawn to the “magic” transformation into a beautiful, if evil, woman. Between those two extremes are a number of mostly forgotten movies which would, while not being great filmmaking, might very well appeal to the person just looking to indulge the escapism of “man gets to be a girl” themes. One such movie I’ll mention is “ladybugs” which was a Rodney Dangerfield vehicle but featured a not quite so cut-and-paste take on the “guy disguised as a girl” trope.

Now, having laid out the ground rules, I immediately am forced to violate them not once but twice, because of the high-profile and well done examples I could not help but list. So, without any more delay, here’s my utterly predicable list of the best cross-gender movies that I have actually seen (and remember!).
6. Victor/Victoria – no real trans person here, but the pretense is of being a drag performer so the theme is related. I enjoyed it for James Garner’s nice turn as a somewhat conflicted love interest.
5. The Rocky Horror Picture Show – the legendary example of “so bad it’s good” movie making. If you take it even the slightest bit seriously, it’s a disaster. But if you turn your brain off then you have to appreciate how very many men this movie eventually got into garter and stockings.
4. Mrs. Doubtfire – No, he’s not trans or a crossdresser by nature, but he does crossdress in the film as a choice, not something he’s thrown into. It strikes a nice balance between some of the rather obvious, gentle, cross-dressing jokes, and the heart of the plot which is the frustrated relationship with his kids. Of course, one really has to suspend disbelief somewhat in accepting that he would actually have been able to fool his ex-wife and the kids (don’t kids ALWAYS clock you first?)
3. Tootsie – The other ”exception that proves the rule” – it’s hard to overstate the quality of Hoffman’s performance or the quality of the script. It’s really a film about gender equality more than it is about transgender themes, of course, but what crossdresser hasn’t dreamed about being able to go out and pull off that kind of integration into the world and not “get caught.” Also, get your Google on and find the video of Dustin Hoffman talking about what the experience taught him, which brings him to tears. Powerful stuff.
2. Transamerica – Oscar-nominated (and should have been winning) performance by Felicity Hoffman highlights what is in every respect a film about being trans, and how it affects interpersonal relationships. It can be very profane at times, it’s not for the refined sensitive minded person – but it’s pretty spot on in the ground it covers.
1. Normal – not a theatrical film, but so so deserving of this spot. As someone who transitioned in a very similar circumstance, I deeply related to the situation of the main character here. I did not find my spouse to be able to come around to being supportive, as happened in the film – but if you don’t cry when the wife says to the minister “but he’s my heart.” then you have no soul.

So, what’s your favorite?

Photo by JanneM