Jon Stewart's David Letterman Underwear Joke Accidentally Mocks 2009 'Late Show' Scandal (VIDEO)

Jon Stewart was a guest on "The Late Show With David Letterman" Wednesday night, and while the two veteran talk show hosts had a funny and cordial interview, they found themselves in a bind when one of Stewart's jokes left Letterman blushing (and Stewart apologizing).

After some talk about GOP presidential candidate Mitt Romney, Letterman remarked that he reminds him of the men who pose for men's underwear packaging. This prompted Stewart to ask if Letterman himself even wears underwear anymore, then he launched into an off-the-cuff bit that quickly derailed:

"I would think at this stage of your career, you have people that could just sit there and hug your groin for you," Stewart told Letterman. "Just hold on. Just do that. You could have like a group of people --"

At this point, Stewart started losing his focus. Letterman's face became uncomfortable as he (and the audience) quickly realized that this sounded oddly familiar. In case you forgot, Letterman admitted in 2009 that he had sexual relations with female members of his staff, specifically his personal assistant.

"Jon, Jon, Jon," Letterman said after an awkward break for laughter. "I had a little trouble along those lines."

With both hosts laughing off the faux-pas, Stewart admitted that he had realized his mistake mid-bit but just couldn't stop. Watch the snag happen in the clip above or Click here to watch the full thing on YouTube.

Comments

[nitwitsRus]

07:26 PM on 02/17/2012

good thing ya didn't bring THIS one up
, he was not drafted for service in Vietnam due to receiving a draft lottery number of 352 (out of 365)
ain't it Jon?

[brux]

05:35 PM on 02/17/2012

Letterman reportedly had a habit of "dating" interns … there is not much difference between that and prostitution. I think he should have just been honest about it. I also think they should find someone else, to host the tonight show, I have been sick of Letterman since less than a year after he started hosting the show. I don't get what people think is funny about him. Anyone can go out and deliver jokes that a whole team of writers writes.

[darcylu]

01:20 PM on 02/17/2012

Letterman's mention of Romney looking like a men's underwear model was hilarious. My husband and I cracked up at that one, and picturing Romney on a package of men's underwear actually caused me to spit a little coffee on my laptop.

He and Scott Brown. I can picture them in a Sears catalog. Both empty suits.

[Teeman1969]

03:55 AM on 02/17/2012

Real people, make real jokes. Dave and Jon are both true comics. I respect both of them. Great minds.

[markburn]

12:46 AM on 02/17/2012

The whole interview, that was quite funny:
http://www.youtube.com/watch?v=A39ebWK4D0g

[angel figueroa]

12:01 AM on 02/17/2012

if you pay attention the joke is actually a reverse on what dave says, he implied that john stewart was to rich to buy he's own underwear interrupting johns punch line being the stage comic stewart is he came back at him with the same style but funnier framed joke about being wealthy but than realized hes joke was taken as involving the incident he had with the staff lady, witch it was not. even this article takes the interaction out of connects.

[catgirl666]

11:53 PM on 02/16/2012

Too funny!!

[Toolologist]

11:15 PM on 02/16/2012

Oops!

[nightingale801]

10:49 PM on 02/16/2012

*lol* "Here, have a pencil"

[LindyK]

09:00 PM on 02/16/2012

Howard Stern has already joked about it on late night and Letterman was totally fine with it. I doubt the joke was an accident on Stewart's part.

[researchgrrrl]

06:43 PM on 02/23/2012

I don't know. Jon Stewart turns genuinely red-faced in this, and he's not someone you'll see blush on-camera very much. I think he really wasn't thinking about Letterman's affairs when he started rolling with the joke and that his embarrassment was sincere.

[aceshigh11]

08:38 PM on 02/16/2012

LOL, that was great!

[salamanca1]

08:01 PM on 02/16/2012

The T Mobile intro ad features a new, younger, updated lithesome brunette in red dress. Must be Catherine Zeta Jones got too old.

[CTDFalconer]

09:19 PM on 02/16/2012

More likely she got too expensive.

[carmillivanilli]

03:56 PM on 02/17/2012

Or maybe she decided she didn't want her name attached to that least-reputable of phone companies.

[kolach]

07:47 PM on 02/16/2012

Haha Dave is a good sport.

[CanuckLad]

07:27 PM on 02/16/2012

Of course he will be invited back, it's getting extra notice.

Many conservatives/republicans have money and pull. Why don't you just make your own comedy shows, movies etc. instead of complaining about what the left does? If there are so many clowns and stupid ideas among the left there must be comedy gold there, go for it!

[ArkayMI]

08:24 PM on 02/16/2012

All the GOP comedians are either running for office or on Faux Noise.

[ticoune]

11:18 AM on 02/18/2012

There's no such thing as a GOP comedian.

[Buller]

10:52 PM on 02/16/2012

You may gave forgotten, but the right wingers did try a faux comedy news show and it was so funny viewers died laughing!
In the interest of protecting the health and life of their esteemed viewers they cancelled it.

[ticoune]

11:20 AM on 02/18/2012

fox news is a feeble account of a comedy show.

[crabbyguy75]

06:49 PM on 02/16/2012

He won't be invited back.

[monstersfromtheid]

10:35 PM on 02/16/2012

when was the last time Letterman got this much attention? He'd have him back every week if he could now.