11 Points

11 Best Gender Bending Moments in Entertainment
written by Sam Greenspan

I'm not sure why the idea for this list came into my head. I'm really not.

Maybe it was watching the giantesses play women's volleyball on the Olympics last night. Really don't know. But, for some reason, I started thinking about cross dressing and gender bending moments I've seen in movies, TV, video games, everywhere. And those thoughts became a list. That's how we always get here.

For this list, I'm not focusing on movie, TV show, etc. as a whole (like, "To Wong Foo" or "Yentl" or "Bosom Buddies"), I'm just focusing on one seminal moment. No pun intended.

  1. It's a (highly pixelated) woman!
    Samus reveals she's a man in Metroid - Nothing caught 10- and 11-year-old boys off guard like finally beating Metroid on their NES... and then finding out the entire time that the hero of Metroid, Samus, was actually a woman.

    For many of us, this was our first true encounter with a gender surprise. (After I spent three months in college interning at the "Jerry Springer Show", for me, it was hardly my last. Some of the transvestites that came in to be on that show were INCREDIBLY well done.)

  2. Felicity Huffman's bathtub scene in "Transamerica" - It's one thing when a respected actress shows her breasts as part of a quest to win an Oscar. It's an entirely new level when she shows her penis.

  3. The reveal scene from "The Crying Game".
    Dil reveals he's a man in "The Crying Game" - Everyone knows about this moment, but I don't know how many people have actually seen it. Tracking down a video of it took much longer than I expected.

    Here's an interesting fact about that scene: Despite popular belief, it doesn't happen at the end of the movie, it happens towards the middle. And then the movie goes back to being about the IRA. Who knew?

  4. Austin Powers revealing that it's a man baby in "Austin Powers" - Only because "It's a man, baby" became one of the many popular "Austin Powers" catchphrases that applied to day-to-day situations and then became unbearably burned out.

  5. Finkel is Einhorn. I don't see it, but Ace does.
    Ace realizes Finkel is Einhorn in "Ace Ventura: Pet Detective" - It's a twist that you never really see coming. Seriously. It's a good one. Also, I never quite understood how Ace figured it out. Like, his dog plops down on top of the Ray Finkel photo, which gives Finkel long hair, and Ace makes the connection. But I never saw it. I just can't get past the mustache.

  6. The end of "Just One of the Guys" - This wasn't just Joyce Hyser revealing to Rick she was a woman disguised as a man... it was her doing that with shockingly fantastic nudity. You watch this movie today and even with an Internet full of porn right at your fingertips, you STILL get giddy at this scene.

    The '80s really knew how to do movie nudity. No one today gets it quite right. (Yes, Dane Cook movies, I'm looking at you.)

  7. Glorious.
    Terry Crews sings "A Thousand Miles" in "White Chicks" - I find Terry Crews hilarious (except in "Everybody Hates Chris", which I just don't find funny at all). In this scene in "White Chicks" (a movie that, against all odds, I find enjoyable and legitimately funny), he's on a date with one of the Wayans brothers (which one isn't important) who's dressed as a white girl.

    It all leads to him singing the Vanessa Carlton song "A Thousand Miles". And that's the moment that makes the movie for me.

    Trust me, it's far better than when the Wayans brothers actually reveal that they're men in drag, or any of the close calls with getting their drag outfits on that happen in every movie like this.

  8. Viola reveals she's a woman and Sebastian is her twin brother in Shakespeare's "Twelfth Night" - I won't go into more detail because I know no one's actually going to read this paragraph, you're just going to skim it because you clearly see Mario Kart below and have no interest in reading what I'm typing here. Philistines.

    Consult your local library or go find some Summer Stock before August is over to find out what I'm talking about here.

  9. Gobe in a dress.
    Gobe unveils his Princess costume in "Real Life Mario Kart" - Sure, maybe it's a cop out to include a moment from one of my old videos on this list. But the moment that Gobe was revealed in his pink dress and wig, it really took our IdiOlympics series to the next level. And I daresay his commitment to that role really contributed to Real Life Mario Kart becoming our most watched video ever.

  10. Screech dressing up as "Sinead O'Connor" to record the girls singing on "Saved By the Bell" - There are two times when Screech dresses as a woman to go into the girls' locker room on "Saved By the Bell". Once, he says his name is Barbara Bush, and he switches out the tapes in the girls' Walkmen for tapes with subliminal messages.

    I voted for the second time he cross dresses to invade the girls' locker room, though, for this list. This time, he says he's "Sinead O'Connor", and gets the girls to sing "I'm So Excited" into his broom. Of course, it's a microphone... he records it... Zack takes the tape... starts making the girls famous... and the next thing you know Jessie's addicted to pills and delivering the most famous line in "Saved By the Bell" history.

    And I'm so excited and so scared that I almost made this list without including this moment.

  11. Robin Williams does shtick in "Mrs. Doubtfire" - I actually don't like this one that much. But I get the feeling that if he stumbled on this list and wasn't included, he'd be really upset. So let's go with the "drive-by fruiting" moment. Hilarious!

This post was originally published on Tuesday, August 12, 2008 at 12:58:42 PM under the category Movies.

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