Conan's 20-Year Blooper Reel Has Ironic Technical Difficulties

10/31/2013 04:53 pm ET
  • Katla McGlynn Senior Comedy & Viral Editor, The Huffington Post

"We're showing a blooper reel and we f***ed it up. How about that?"

Oh, Conan. As if we could love you more.

As Team Coco celebrates 20 years on television this week, remember all of Conan's most awkward moments with the blooper reel above. You'll see unreliable props, a kangaroo in heat and some of the cutest little old ladies you'll ever hear singing off-key around the 5:54 mark.

The best part? The ironic technical difficulties that cause Conan to have to start the blooper reel over. Amazing.

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10 Hilarious News Blooper GIFs