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How to Cross Dress For Comedy

by Jessica De Leon on April 13, 2011

On television, in movies and on YouTube I’ve seen male countless performers going for cheap laughs with a half-hearted female costume. I suppose what really drove me to produce this satirical video was seeing so many “comedians” on YouTube play female characters with exaggerated makeup, over-the-top balloons in their shirt and sloppy wigs, among other things.

The icing on the cake for these “comedians” is when they use that high-pitched falsetto voice that Monty Python used back when it was funny. Nowadays, it’s just tired and lame.

Man + Drag = Instant Funny

Perhaps some of the inspiration and creative energy for this video came from the fact that it takes me sometimes two hours to shave, apply makeup and choose an outfit before I can perform as Jessica Who? (when not performing I am simply Jessica De Leon).

With that in mind, I present my sarcastic step-by-step instructional video tutorial on how to transform from male to female caricature.


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{ 7 comments… read them below or add one }

Angie April 13, 2011 at 12:39 pm

Great work as always, keep it up.

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Jessica De Leon April 14, 2011 at 12:27 pm

Thanks Angie!

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Alyssa April 13, 2011 at 7:33 pm

I’m doing papers on the brilliant satire of Mark Twain and Kurt Vonnegut. Let me say, Jess, your work is right up there. Keep it up!

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Jessica De Leon April 14, 2011 at 12:39 pm

Wow, thanks for the awesome compliment :)

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jessica April 13, 2011 at 9:14 pm

misses butterworth :-)

I don’t think sloppy drag still works in this day n age, we have higher standards now

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Jessica De Leon April 14, 2011 at 12:27 pm

Hehe, you’d be surprised. Check out some episodes of SNL (Estro-Maxx) and I’d say 70% of the “comedians” on YouTube. Unfortunately, audiences still eat it up like a succulent Thanksgiving turkey.

That’s why I was so motivated to do this satire :) .

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Julie M Shaw April 21, 2011 at 11:47 am

Your sense of humor is very sharp. Your wit comes through – which is one of the hardest kinds of comedy (in my humble opinion) while you don’t go for the “cheap laugh”. Thanks for sharing with us all.

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