Jon Stewart and Friends Use Chatroulette on The Daily Show

Tonight, Jon Stewart finally—and brilliantly—jumped on the Chatroulette bandwagon. Stewart mocked the media's obsession with the Internet's newest fad, before trying it out himself—and running into Diane Sawyer, Keith Olbermann, Katie Couric, Brian Williams and others. Video inside.

Stewart's Chatroulette segment began with a satirical look at the media's interest in the web site (and its apparent naivety of the fact that there is a lot of penis there).

Then, Stewart decided to try the site out for himself—and it was awesome. Who did he run into? Well, among others (all of these were real conversations between the two, by the way):

• Diane Sawyer, who wasn't too excited to see him and "Nexted" him rather quickly,
• Keith Olbermann, who went on one of his normal diatribes before saying, "I think one of us is supposed to take our pants off now,"
• Katie Couric, who asked Stewart to be interviewed for a segment she was doing on the site before setting it up as a place full of "deranged criminal perverts,"
• and Brian Williams, who seemed to be there just for fun.

How did Stewart get all of the aforementioned to agree to do this segment with him? I have no idea, but I'm sure as hell glad he was able to pull it off.

Bonus: [CLICK HERE] to see screengrabs that I took of each of Stewart's notable encounters from the segment.

[The Daily Show with Jon Stewart]

Send an email to Matt Cherette, the author of this post, at matt@gawker.tv.

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