Crossdressing on Late Night with Jimmy Fallon

by Jessica Who on September 15, 2009

While watching television late last night, I caught a new skit on Late Night with Jimmy Fallon. It’s called “The Real Housewives of Late Night” and features Mr. Fallon and several members of the staff from the show playing their own wives.

Keep reading for the video, a related link and my take on this new (recurring?) comedy sketch.

This video had me cracking up and in awe of the great job that the show did in transforming these five men into their own wives. It wasn’t enough that they got in drag for that is something that has been done to death in television, movies and such. They went the extra mile and really took on their characters — obnoxious, annoying wives.

They are all pretty convincing and I wonder whether or not any of them are actually crossdressers. I really hope that they keep this series going for at least a few more episodes, I really enjoyed it. It looks like they had a great time doing this and I would have loved to be part of the staff on that day.

Last week, they featured a poll on the best men dressed as women in film, which you can find here. As we’ve discussed before, it’s very reassuring to see other men cross-dressing, even when it’s in a comedy. I always feel a bit more confident in myself when I see other men doing this.

Here’s another clip of Jimmy Fallon playing his wife Denise:

I hope that as cross-dressing is taken a bit more seriously (even when in fun) in mainstream media, we gain more acceptance. Comedy is a great way to break down barriers by pushing the envelope and making light of something that is normally very serious.

So, what did you think of these clips? Would you like to see more of this on Jimmy Fallon’s show? Let me know what you think by posting a comment below ;) .

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{ 18 comments… read them below or add one }

Jess McClure September 15, 2009 at 10:22 am

What a great find!! Thank you very much for sharing this! NBC should make a spin-off show based on this concept.

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Jessica De Leon September 15, 2009 at 10:28 am

Thanks Jess! My wife and I laughed hysterically when we watched this, I would love for it to become a spin-off =)

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Julie M Shaw September 15, 2009 at 1:10 pm

Downright hysterical! Thanks for sharing this, sweetie!

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Jessica De Leon September 15, 2009 at 2:20 pm

:) , I’m glad you enjoyed it

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lynnd September 15, 2009 at 3:03 pm

Thank you for posting that. I agree, it is hysterical.

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Jessica De Leon September 15, 2009 at 3:04 pm

:D … We need to write NBC and ask them for more :) !!! lol

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Lynn Jones September 15, 2009 at 4:19 pm

Thanks for sharing – it raised some laughs.

Was no-one in heels tho? Lightweights :-D

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Jessica De Leon September 15, 2009 at 4:20 pm

That’s true — I didn’t even look at the shoes, though Denise had a very nice bag ;)

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Stephanie September 15, 2009 at 4:24 pm

Very awesome find, I think even for latenight comedy it was tasteful (well as tastful as late night comedy gets) As long as it didn’t turn into another Cavemen, I think it gets my vote for spin off.

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Jessica De Leon September 15, 2009 at 4:33 pm

Yay! I’m going to have to start a petition for NBC ;)

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J September 16, 2009 at 4:26 pm

that was amazing! they were all really convincing! (well some more than others, but still.) i kind of like that they were doing generally earnest impressions of their wives, and not just over the top “look at me, i’m dressed like a woman, but i’m so clumsy i could never be taken seriously and my sexual orientation will not be called into question because i’m clearly a dude!”

very funny :)

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Jessica De Leon September 16, 2009 at 4:27 pm

Yea, you’re so right, great insight J :)

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Stephanie Kay September 17, 2009 at 10:33 am

This is a real hoot!! It was very clever!! I hope they do more!
PS. I wish I had the help of a Hollywood make-up artist!!

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Jessica De Leon September 18, 2009 at 1:40 pm

Yea, they are pretty lucky to have professional stylists and makeup artists. It would be so cool if they made more skits like this.

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june maddon September 24, 2009 at 10:56 pm

That was so hysterical,It was done very nice and the makeup and dress was great .Dale and the band member looked outstanding.Maybe Dale is a closet queen he really great.

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Jessica De Leon September 25, 2009 at 6:58 pm

I wondered the same thing about Dale. His mannerisms are spot on :) !!

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Tracy August 12, 2011 at 10:42 am

making this comment almost 2 yrs after the original post. I think I have seen most of the “Real Housewives/Late Night” skits. Can’t recall anything specific but I seem to recall seeing him doing other crossdress skit roles. He did one last night (8/11/11) and realizing I’ve seen him do that on many occasions wondered if is a crossdresser or simply enjoys pushing the envelope (could be both too). It did strike me how well him and several of the guys did as their wives in the RHoLN skits. :-)

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jonathan September 11, 2011 at 9:10 pm

I downloaded flash 10, over downloaded real player (downloaded over top of) I can see nothing except your blog Jessica.
I guess these Jimmy Fallon episodes are for a select few and I’m not in the bunch?

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