Jon Stewart's Letterman Faux Pas Is Hilariously Awkward (VIDEO)

LOL 19

David Letterman seems to get a kick out of making his guests squirm, and last night was no exception when Jon Stewart appeared on the show. However, you can't really blame Letterman for what happened, because Stewart managed to walk right into what ended up being a hilariously uncomfortable moment for both of them.

It started when Letterman was joking about Mitt Romney, which somehow morphed into a conversation about underwear, and ended up focusing on Letterman's personal underwear. Specifically, whether or not Letterman has staff members whose jobs might involve attending to his groin area, a joke that quickly went off the rails because ... well, because he sort of DID, back in 2009.

Ha ha! It's horribly awkward because it's true!

As you may remember, Letterman weathered a rather nasty scandal in 2009, which involved a CBS producer attempting to blackmail him for $2 million in order to keep quiet about Letterman's various affairs. Letterman eventually publicly admitted that he'd had sexual relationships with female employees who worked with him on his show, including his personal assistant.

Which is why Jon Stewart's joke last night was so awesomely, hilariously, cringe-ingly hilarious.

Here's what happened: Stewart was riffing about Letterman's underwear, and went on to say, "Do you even have to wear underpants? I would think at this stage of your career, you have
people who could just sit there and hug your groin for you."

If you watch Letterman's face at that moment,
it's pretty priceless. He finally interrupts Stewart with, "Jon, I had a little trouble along those lines."

Haaaaaaaa. Yeah, "a little trouble" sounds about right.
Here's the video in all its awkward glory:

I love how Stewart tries to explain himself there at the end:

Can I tell you something terrible? I'm halfway through that bit and all of a sudden I realize ... what the fuck am I doing?

To be honest, I think Letterman could have easily let Stewart get through the joke without interrupting him by calling attention to his past misdeeds—but it's much, much funnier that he did.

Did you get a laugh out of this uncomfortable TV moment?

Image via YouTube



To add a comment, please log in with

Use Your CafeMom Profile

Join CafeMom or Log in to your CafeMom account. CafeMom members can keep track of their comments.

Join CafeMom or Log in to your CafeMom account. CafeMom members can keep track of their comments.

Comment As a Guest

Guest comments are moderated and will not appear immediately.

godde... goddess99

Love David. Handled it like a professional.

nonmember avatar Cara

It was funny. If you can dish it, you should be able to take it. Letterman clearly can.

nonmember avatar hs


(Keep it goin yall)

Kmakk... Kmakksmom

I love it!  I've been watching Letterman since I was younger.  He's great.

LOswa... LOswald0314

Hilarious! I love that Letterman is so candid.

amy7243 amy7243

Love it!!

daerc... daerca574

that is great!

1-10 of 19 comments 12 Last