Weekend Roundtable: Best & Worst Gender-Swapping Movies

That Tyler Perry sure likes to dress in drag, doesn’t he? With this week’s release of yet another of the writer/director/star’s ‘Madea’ movies, we thought that we’d use today’s Roundtable to look back at some of cinema’s other notable films about cross-dressing shenanigans.

We’ll even allow one TV show in here for good measure. Why not?

Luke Hickman

Best: Michael J. Fox in ‘Back to the Future, Part II‘. Why? Because it’s short and sweet, and not a major character.

Worst: John Travolta in ‘Hairspray‘. Let’s be honest, Travolta has only been in a couple of good movies. Watch ‘Wild Hogs’ and/or ‘Old Dogs’ and you’ll see exactly why he’s not worth watching anymore. Throwing him in a fat woman’s suit only makes him even less tolerable. I’d rather have that gypsy from ‘Drag Me to Hell’ turn me into a fat woman than have to watch that absurd performance again.

Tom Landy

Worst: Considering that gender-swapping movies usually tend to be a pet peeve of mine, it’s safe to say that I can’t really come up with a favorite. Most of the comedies I just don’t find all that humorous, and when we’re talking more serious dramas such as ‘Boys Don’t Cry’… I’m sorry, but I just didn’t buy Hilary Swank as a man at all. As for the worst of these kinds of films, they probably don’t get much more terrible than 1994’s ‘It’s Pat‘. In this spinoff movie from a recurring ‘Saturday Night Live’ sketch, Julia Sweeney stars as “Pat,” a creepy and unfunny humanoid that no one seems to be able to determine whether it’s male or female. Kind of like talk show host Wendy Williams. Anyway, how Pat beat out Toonces the Driving Cat for a feature film is beyond me, and will forever remain one of life’s greatest mysteries.

Mike Attebery

Best: The witty, pitch-perfect script for ‘Tootsie‘ is a staple of screenwriting classes for a reason. Dustin Hoffman was at his “difficult but talented” peak. This is quite possibly Sydney Pollack’s best film as a director. (He’s also perfect as Hoffman’s long suffering agent.) The cast is packed with perfect co-stars: Teri Garr, Jessica Lange, Bill Murray, Charles Durning, George Gaynes and Dabney Coleman. Need I go on?

Worst: Anything ‘Big Momma‘. Where ‘Tootsie’ has wit, sophistication and humor, these movies have Martin Lawrence.

Brian Hoss

Best & Worst: Kathleen Turner in ‘Friends‘. When I was young, one of the movies that my family enjoyed was ‘Romancing the Stone’. Even as a kid, I thought that Kathleen Turner was pretty sultry running around the rainforest. Time passed, and the show ‘Friends’ finally decided to introduce Chandler Bing’s often-mentioned father, Charles Bing. Charles Bing had apparently decided to become a showgirl post-Bing family unit. At some point, seeing ‘Friends’ episodes in syndication, it clicked that “Charles Bing” was Kathleen Turner. It still boggles my mind that the woman who starred in ‘Romancing the Stone’ and voiced Jessica Rabbit wound up as Chandler Bing’s showgirl father. It was kind of like when I thought I caught ‘Romancing the Stone’ on cable, and it turned out to be something called ‘Jewel of the Nile’.

Josh Zyber

Best: So, umm, like, Spoiler Alert: That chick in ‘The Crying Game‘ is really a guy. Whoops, did I just ruin the surprise of this 20-year-old movie for you? More so than the fact that the performer in question eventually received an Oscar nomination for Best Supporting Actor rather than Actress? It’s a pretty famous movie with an incredibly famous plot twist, so this is really nobody’s fault but your own.

That said, one of the greatest strengths of ‘The Crying Game’ is that the film isn’t totally reliant on the gimmick of its plot twist. I first saw the movie long before it had built up any popular buzz or Oscar hype. At the time, it was just a little art film that had gotten a good review in my local paper. I wasn’t aware that it supposedly had a twist at all. Honestly, even so, I figured out that Jaye Davidson was a man pretty early on. Something about his chin just didn’t look right. That didn’t (and still doesn’t) matter. This is one of the most perfectly scripted movies I’ve ever seen. It doesn’t have a single unnecessary scene or line of dialogue. The story is thematically rich on numerous levels, not the least of which are its explorations of gender and identity. This is director Neil Jordan’s most perfectly realized film. It’s a masterpiece.

Honorable mentions to Billy Wilder’s classic ‘Some Like It Hot‘ (which is obviously where today’s banner image comes from) and Tilda Swinton’s gender-defying performance in ‘Orlando‘.

Worst: As much as I respect David Cronenberg, and as much as his 1993 adaptation of the stage play ‘M. Butterfly‘ is a fascinating failure, the film is undeniably a failure all the same. The primary reason for that is John Lone’s inability to convincingly play a woman. He has the wrong body type, the wrong face, the wrong mannerisms, everything. Although a fine actor otherwise, he was just flat-out miscast here. There’s simply no way that Jeremy Irons’ French diplomat character could be fooled by this ruse, no matter how much he wanted to believe it. (One of the story’s primary themes is the power of self-delusion.) Because the audience cannot suspend disbelief over this aspect, the whole thing falls apart. It’s a shame, because the material is actually pretty strong. This was just a huge miscalculation on the director’s part.

Don’t be ashamed to admit that you’ve watched a cross-dressing movie or two in your time. Tell us about your picks for best and worst in the Comments.


  1. JM

    Dog Day Afternoon?

    Hedwig and the Angry Inch?

    The Silence of the Lambs?

    The Skin I Live In?

    Ticked-Off Trannies with Knives?

    The World According to Garp?

    Itty Bitty Titty Committee?

    Dr. Jekyll and Ms. Hyde?


    The Rocky Horror Picture Show ?

    La Cage aux Folles?

    Nuns on the Run?

    Color of Night?

    To Wong Foo, Thanks for Everything! Julie Newmar?


    Shakespeare in Love?

    Ed Wood?

    Monty Python’s Life Of Brian?

    The worst is either ‘The Hot Chick’ or ‘Albert Nobbs.’

    • EM

      Tim Burton’s Ed Wood is an entertaining movie, but in terms of gender-swapping it owes much to the real Ed Wood’s Glen or Glenda, which features in Burton’s film. While Glen or Glenda is beset by Wood’s trademark ineptitude, it remains at heart an honest plea for understanding of and compassion toward transvestites and (to a lesser extent) transsexuals. (It is also a threadbare excuse to shoehorn in Béla Lugosi getting all spooky-like.) Sure, Wood himself was a transvestite (who hijacked the production, originally envisioned as sex-change exploitation, to focus on his own interest, using a stage name to star in the picture while crediting his behind-the-scenes work with his real name)—but that doesn’t change the fact that the film’s call for more enlightened attitudes is quite ahead of its time. Perhaps Glen or Glenda’s saddest scene is the one in which the narrator acknowledges the audience’s laughter at the sight of a bearded man in drag—I’ve never laughed at that image, but I’m sure Wood was right to predict that many viewers, especially in the 1950s, would.

  2. Mike Attebery

    Brian, I like your pick!

    Kathleen Turner boggles the mind. Have you seen her in Marley and Me (lets not get into why I have)? Horrifying? Like Josh says, Body Heat to the sweatpant clad dog trainer in Marley and Me? The head spins.

  3. Alex

    I’m surprised no one mentioned Mrs. Doubtfire (either as a favorite or a least favorite, as its a pretty polarizing movie). I haven’t seen it in years, but I remember loving it when I was younger.

    Some Like It Hot is a crack-up too.

  4. EM

    Best: Psycho (1960). Oh, I hope I didn’t spoil it!

    2nd: Alien, with its deadly twist on childbirth.

    3rd: Jesus Christ Vampire Hunter, in which a transvestite takes on the role of the Good Samaritan.

    • EM

      Officially, Joan was prosecuted for heresy and insubordination. The reality behind the trial was political, as Joan was the defender of a king whose throne had been hotly contested. Joan claimed that God himself drove her actions as a soldier, and both the historical trial and the film overtly focused on that question. The exact meaning of the term transvestite has fluctuated over the years—even in purely polite usage—but I think labeling J. of A. one is obfuscatory. To my knowledge, there’s no reason to believe that Joan wore male attire to satisfy a sexual fetish or her own sexual identity or even out of personal preference for male sartorial styles. In an era in which her vocation was supposed to be off-limits for her gender, dressing as a male allowed her to travel in disguise, ward off the impure attentions of her fellow soldiers, and wear the standard equipment of her job. Joan did cross gender boundaries, but her choice of attire is probably the least remarkable of her achievements.

        • EM

          I don’t recommend substituting religion for truth. I imagine cross-dressing may have added fuel to the fire (no pun intended), and I certainly believe that Joan was treated more harshly than a young man in her (non-gender-bending) position would have been. To the extent that her “crimes” were gender-related, they probably instilled less ire for their violation of religious dogma than for their challenge to male domination (her prosecutors were, of course, all male). Again, politics.

  5. Kelly

    Have you seen the trailer for ‘Alex Cross’? Tyler Perry’s acting looks atrocious. I just don’t get it.

  6. I am going to throw out a movie that I bet most of you have not seen – Hilfe, Ich Bin Ein Junge!. Disney picked it up, and released a horrible dub of it (that should be available on Netflixe) and its called Help! I’m A Boy!

    Ever seen the movie “Freaky Friday”? Well, imagine the same thing, but it happens between an 11 year old boy and girl instead. Great movie, especially love the part when he wakes up as a girl, and goes to take a piss, and “can’t find it”. 🙂 Anyways, unlike Freaky Friday, where their bodies stay in the same place and the conciousness just move, instead they morph into each other, at night. So, between their bedclothes, and then having to find clothes just to be able to leave the house in, they spend the majority of the movie cross-dressed as well.

    Anyways, if you speak German, definately watch it in the original German. I also fansubbed it, just not really sure how to distribute the subtitles. Worst case scenario, just pull the dubbed version off of Netflix. I am almost positive it is there, but Netflix is failing tonight on my PC, Roku, TV, PS3 and my phone. It is available to rent for $2.99 on Amazon, to buy for $7.99 on Amazon, and its available for $2 to rent on Vudu and $9.99 to buy.

    Remember, if you are looking for it on Netflix, Amazon, or Vudu, its Help! I’m A Boy

    If you are looking for the original German disc, it’s Hilfe! Ich Bin Ein Junge