Gumdrop Lane


Men have been dressing as women for entertainment purposes for eons. Let us revisit the fact I learned from Shakespeare in Love that men used to portray all the women’s roles in theatrical productions. Men dressing as women is simply a far more common occurrence than women dressing as men, which I previously discussed. Therefore, selecting the best and worst was a very tough process, as the choices are far greater. However, I believe I’ve whittled the best and worst down to a choice few.

Some of these men weren’t just unattractive as women in a way that made them unconvincing, but simply had no devotion to their female persona. Dedication to persona is a key part in cross-dressing in film and TV. The following, or “best” choices, I feel are men who were truly dedicated to their female persona.


This is one of my favorite films in large part to Dustin Hoffman’s portrayal of Dorothy Michaels. He somehow vaguely reminds me of Bea Arthur – and not just because their beloved characters share a name. Their disparate heights alone should sway me but it doesn’t. Bea and Dorothy Michaels are both slightly mannish, slightly ladylike and both no nonsense charmers. Dustin does such a good Dorothy a senior citizen falls in love with him/her. If that doesn’t spell the best, I guess I can’t spell.

Some Like It Hot

Can you even spot the fellas in this photo? Well, sure, since they’re the least cute – especially when standing next to the goddess Marilyn, but they still manage to jazz their way into an all-girl band. They become best girlfriends with Marilyn and one of them even gets a proposal. Looks like Dorothy Michaels might have some competition! And it looks like senior citizens are totally irresponsible, trying to get hitched to strangers they barely know. They haven’t even seen these guys’/gals’ genitals! What if they’re not to their liking? They don’t know. Stupid senior citizens…

Mrs. Doubtfire

Robin Williams has the most convincing feminine voice. I wish he would read audiobooks in his Mrs. Doubtfire voice. His transformation into the dude who looks like a lady also involves a delightful makeover scene, of which I’m a huge fan and he dances around with a vacuum cleaner! What a kooky misfit! I know as a woman one of my primary goals each day is to dance with my vacuum cleaner. A gal dressed as a guy dressed as a gal can dream…


Ladybugs is life. I’ve briefly discussed the film before. I’d mention it everyday if I could. Jonathan Brandis is brilliant as an excellent soccer-playing guy disguising himself as a girl in order to help his mother’s boyfriend’s boss’s daughter’s soccer team look good. You heard that right. That convoluted story line makes an excellent movie and we watch with joy as Jonathan falls in love with the boss’s daughter and a soccer team full of misfit scamps!

Arrested Development

That clip says it all.

Jack and Jill

Honestly, I didn’t see this movie. The trailer rendered that unnecessary  I don’t think Adam even tried. Maybe he needed the money to buy another yacht or something. I don’t know. An abomination.

Bosom Buddies

Again, to be honest, I’ve only seen a couple episodes and was not that amused. Their wardrobe is basically from the Golden Girls reject pile. But mostly they go in the worst pile for dumbest sitcom title. “Get it, they have BOOBS and “bosom” is both a word for BOOBS and close friends! Genius!!” Until apparently the 2nd season when they cut way down on the whole cross-dressing element. C’est la boobs, I guess.

White Chicks

They don’t even look like human people. They look like weird sex dolls. Or…no. They just look like weird sex dolls from that crazy documentary I saw on TLC about people in relationships with sex dolls. Fail.

Images via,,,,,,

  • Diana Turetsky

    you forgot Chad Lowe in “Nobody’s Perfect”. I loved that movie when i was younger partially because i loved Stephen’s/Stephanie’s struggles.

  • Robin Gropp-Speight

    I applaud your choices, but Kip and Henry from BOSOM BUDDIES are still in my top 5.

  • Matthew Alcala

    What about Tyler Perry as Madea? What about the Too Wong Foo trio? These are some of the biggest cross-dressing characters in film!!

  • Matthew Alcala

    There is a clear bias toward only White actors playing women (or Wayans playing “White chicks”). I thought I would point it out. Stay critical y’all but I love the effort still.

    • Laura Kadner

      I was going to include To Wong Foo and then totally forgot! I LOVE IT!! It was one of my favorite movies as a kid, oddly enough.

      And I’m sorry but I’m not sorry can’t get behind Madea and Martin Lawrence doing whatever it was he did because those were genuinely unwatchable movies for me.

      And speaking of diversity I completely forgot to include Margaret Cho in my last article about ladies dressing as dudes for her portrayal of Kim Jong-il. Cause that was amazing.

  • Mark Whitener

    The Kids in the Hall often dressed as Women and a few of them were very convincing.

  • Guillermo Verde

    Would it be more culturally sensitive if we pointed out that both Martin Laurence and Tyler Perry make horrible movies where they essentially portray absurd racial stereotypes of their own people? Or shouldn’t we just skip them? And black actors crossing the race and gender barrier isn’t diverse enough? Poots to you. Have to agree on Too Wong Fu and add Pricilla to the pile.

  • Guillermo Verde

    The Waynes brothers crossing barriers of gender and race ain’t diverse enough for ya?

    • Guillermo Verde

      Why did I restate the same point twice?

  • Matthew Alcala

    If there were more people of color on film, there would be more opportunities to show different types of characters and not just the stereotypical ones. Are all White women like Mrs. Doubtfire? No because the characters stands for itself, just like Madea should. Tyler Perry doesn’t claim Madea to represent all Black people. I just wish this blog would showcase more ethnic and cultural diversity.

  • Jessica Jose

    You should see Jimmy Fallon dressed like a woman. bAM!

  • Alyssa Christine Lladoc

    Nevertheless, the Wayans Brothers are hilarious in their White Chicks characters<3

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