The Masturbating Bear Crashes Conan’s Show In Chicago | Late Night with Conan O’Brien

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Published on November 5, 2021

(Original airdate: 05/09/06) The Masturbating Bear is in New York and there’s nothing he can do about it … or is there?

ABOUT LATE NIGHT WITH CONAN O’BRIEN
Running from 1993-2009, Late Night with Conan O’Brien is one of the most beloved late night shows in television history. Known for its absurdist humor, hilarious celebrity interviews and featuring the best stand-up comedians and musical acts of the 90’s and early 2000s. Hosted by Conan O’Brien alongside sidekick Andy Richter and house band Max Weinberg and the Max Weinberg 7, Late Night with Conan O’Brien featured unforgettable segments like “If They Mated,” “In the Year 2000,” “Desk Driving” and made a breakout star of Triumph the Insult Comic Dog.

ABOUT TEAM COCO
Team Coco is the YouTube home for all things Conan O’Brien and the Team Coco Podcast Network. Team Coco features over 25 years of comedy sketches, celebrity interviews and stand-up comedy sets from CONAN on TBS and Late Night with Conan O’Brien, as well as exclusive videos from podcasts like Conan O’Brien Needs a Friend, Literally! with Rob Lowe, Why Won’t You Date Me? with Nicole Byer, The Three Questions with Andy Richter, May I Elaborate? with JB Smoove and Scam Goddess with Laci Mosley.

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11 comments

  • Yogrannyloveme 2 years ago

    You all liked what you saw?

    Reply
  • Avvv Qvvv 2 years ago

    my favorite tv character of all time

    Reply
  • palmerlp 2 years ago

    No matter how many times they do this joke it kills me every time.

    Reply
  • Guys Night Lab 2 years ago

    The good ole days of Late night!!! my buddies and I would watch this when were in college back in 06… Good times!!

    Reply
  • Sameer Pandya 2 years ago

    I was there at this in Chicago. Best part was I made all my friends sign up for the ticket lottery, and I was the only one to get them. In the comments section of the application, I wrote ‘give me tickets or I will cut you.’ I like to think someone at the show saw that, and knew I was Team Coco fanatic channeling Pimpbot 5000.

    Reply
  • fejic 2 years ago

    The fact that they paid someone to dress up as the bear and jump out of a plane

    Reply
  • Thomas James 2 years ago

    This is just dumb.

    Reply
  • Vincent Falcone 2 years ago

    Poor bear would be cancelled today for toxic masculinity.

    Reply
  • Chris Leon 2 years ago

    Not that funny anymore

    Reply
  • ellman10 2 years ago

    I love you Conan.

    Reply
  • Ronny Holmberg 2 years ago

    Well this is funny and all, but where the heck is Wikibear?

    Reply

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