03.19.10

6 Funniest Chatroulette Videos

From the piano-playing improviser to Jon Stewart’s adventures down the rabbit hole, WATCH VIDEO of the funniest moments to emerge from the latest Internet sensation.

What sounds like a French cat-gambling website is actually an Internet phenomenon that allows web cam users to connect with each other at random with the click of a button. Chatroulette has quickly become a place to see the Web’s best (thousands of people connecting with one another using cutting-edge technology) and its worst (thousands of people pleasuring themselves in front of random, disgusted strangers.) But like any Internet success, it’s also spawned countless videos, made both about—and on—the site. Here are six of the best.

Chatroulette: A Scientific Study

This is a brilliant bit of social science from filmmaker Casey Neistat. But is the fact that straight male Internet users would vastly prefer talking to a cute girl over other straight male Internet users really a revelation?

Chatroulette Head-Turn Trick

If you’re not a cute girl, there are other techniques to keep people chatting—like this game, which was so engrossing it was even able to get one of Chatroulette’s notorious masturbators to stop for a moment.

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Chatroulette Piano Improv

Or—if you’re neither a cute girl nor the creator of a cute game—one way to keep your Chatroulette interlocutors interested is to sing to them. About themselves.

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ChattyJerk and the Math Genius

Like any long-term Internet fad, Chatroulette doesn’t just spawn fan-made videos, it creates minor Web celebrities. Like ChattyJerk, the foul-mouthed, mask-wearing curmudgeon whose videos of himself berating people he meets on Chatroulette have thousands of views on YouTube.

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Jon Stewart Checks Out Chatroulette

How big is Chatroulette? Big enough to warrant a segment on The Daily Show—and big enough to garner guest stars, too.

Chatroulette's Shirtless Bird-face Donkey Man

The scary thing about this is that there are real people out there on Chatroulette who are much, much creepier than this guy.

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