The Top 10 Funniest ChatRoulette Screenshots & Videos

Tina Sieber 31-03-2011

<firstimage=”//”>chatroulette screenshotsChatRoulette is a video chat site that randomly matches people for a fun chat. Users from around the world can interact via instant message, webcam, and voice. Everyone is anonymous and no login of any kind is required to participate. Let anarchy reign!


In fact, every visit on ChatRoulette is almost guaranteed to be an entertaining and possibly shocking experience. My screenshots and the YouTube videos below prove it.  Can you come up with more hilarious shots? Post them in the comments!


Many people hide their face behind a mask. This is probably the most primitive I have seen, but I love how he’s wearing his glasses on top of it.

chatroulette screenshots

Mammal Hat

Mickey Mouse or Yogi Bear? I’m undecided. Either way it’s a mammal and the sad face doesn’t match.

chatroulette pics


Camouflage Suit

What does the tag say?

chatroulette pics

Smoking Hot

I hope it’s legal, but I’m afraid the guy in the background looks a little too stoned for that.

chatroulette pics



This guy had a little stickman walking up and down his screen and doing all kinds of funny things. Here it is shooting a rocket.

best of chatroulette

The Glasses

Not only does he win the night’s prize for coolest glasses, also notice the sexy tan lines!

best of chatroulette


Next to masks, glasses are the number one way to “protect yourself How To Protect Yourself When Doing the Chatroulette Shuffle Read More ” on ChatRoulette. Also see this guy:

best of chatroulette

Everything OK?

Does anyone know what this is? Doesn’t look like the glasses came with it.

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This young man figured out how to really stand out: combine a mask with cool glasses.

The Top 10 Funniest ChatRoulette Screenshots & Videos ChatScreen10

The Mask

Nothing, however, beats a great mask like this one.

The Top 10 Funniest ChatRoulette Screenshots & Videos ChatScreen07

Apparently, it is a very popular mask as I later saw a different guy with essentially the same model.

chatroulette screenshots

Beautiful Blue Eyes

Obviously, this is a camera effect and not a reason to be worried.

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The above Chatroulette screenshots were taken during a one hour marathon. Yes, those are the kinds of people you will run into. Don’t believe it? Try for yourself and share your results with us!

Now let’s see what other people found on ChatRoulette. These are the 10 most hilarious ChatRoulette YouTube videos. Enjoy the show!

Funny Piano Improv #1

This is the most viewed ChatRoulette video on YouTube and rightfully so. The man is highly skilled and hilarious!

Master Of Disguise

Meet Batman on ChatRoulette…

Find out more about Spidey Roulette on this Tumblr Blog.

The Last Exorcism

Believe it or not, the movie was apparently promoted on ChatRoulette. This video shows the best reactions.

Funny Improv Pranks

This is one of the best improv series out there. Original and funny.

Rupert On The Web

Hilarious ChatRoulete puppet show!

Edarem vs. Chat Roulette

There are several videos with Edarem floating around. From the ones I have seen I find this by far the weirdest.

Girl In Bikini

Are you attracted to her?

Funny Prank

The girl in this prank is having fun with multiple camera inputs. Watch her freak out the guys.


Best Of Chatroulette

If you turn your head…

Chatroulette Love Song

This may not be the most funny video, but it’s pretty incredible. Whether or not Diana shared her number with the guys is unknown.

You will find more funny ChatRoulette screenshots here:

Which of the screenshots and videos were your favorites? Or can you beat them with something even better?

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  1. Hel M.
    April 9, 2011 at 6:38 pm

    The "everything ok" one is a CPAP mask.

  2. Reygun30012
    April 9, 2011 at 5:48 pm

    Chatroulette Love Song

    • Jessica Cam W.
      June 26, 2011 at 9:58 pm

      I totally agree! So well-planned!

  3. Rupert on the Web
    April 1, 2011 at 4:52 pm

    Thanks so much for including my video on here! (I'm the puppet) I've not had too many hits so far, but keep trying to spread the joy! Chatroulette is a very entertaining place, full of fun and interesting people... and some maniacs!!

    • Tina
      April 1, 2011 at 5:04 pm

      Most welcome Rupert! I loved your show. :)

  4. Ben Wallis
    April 1, 2011 at 10:58 am

    The "popular mask" is from the excellent movie "V for Vendetta"

  5. Ben Wallis
    April 1, 2011 at 8:58 am

    The "popular mask" is from the excellent movie "V for Vendetta"

    • Tina
      April 1, 2011 at 5:06 pm

      I didn't see that movie. So I guess they used Guy Fawkes masks in the movie. Thanks for the input Ben, Sergei and everhopeful! :)

  6. Guest
    April 1, 2011 at 5:36 am

    That is a CPAP (Continuous Positive Airway Pressure) mask people wear at night when they have Sleep Apnea (a medical condition where people stop breathing while sleeping). There are many types of masks out there. Here's a better view of what they look like: [Broken URL Removed]

  7. Anonymous
    April 1, 2011 at 4:09 am

    "The mask" shots are Guy Fawkes masks. Go forth, and google "Guy Fawkes". And also, remember, remember, the fifth of November....

  8. Sergei Trinho
    April 1, 2011 at 2:40 am

    The famous mask...they are very popular among anonymous group.

  9. Mavourneen Strozewski
    April 1, 2011 at 2:30 am

    This is Hilarious stuff!!! Thanks for sharing never heard of Chat Rouelette before!

  10. Slide Buddy
    April 1, 2011 at 1:43 am

    What is up with that "everything ok" screenshot? Was that duct tape on both his forehead and chin?! Lols, my friend tried ChatRoulette a few times, and he told me it was, as you've said, both fun and shocking activity.

    • Tina
      April 1, 2011 at 3:37 am

      As Ray pointed out above it's a C.P.A.P. mask. It helps people with sleep apnea breathe. See the entry positive airway pressure on Wikipedia.

  11. Ray Medrano
    April 1, 2011 at 12:52 am

    The thing in the "Everything OK?" shot is a C.P.A.P. Mask.

    • Tina
      April 1, 2011 at 1:36 am

      Thanks for the clarification, Ray!

  12. Dmitry Kuzmin
    April 1, 2011 at 12:38 am

    "Camouflage Suit" - ??????? is a russian SWAT. What did he say? :)

    • Tina
      April 1, 2011 at 1:36 am

      He actually didn't have the chance to say anything, I ran! lol

      • Dmitry Kuzmin
        April 1, 2011 at 1:40 am

        You did the right thing!