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I must of missed this when it originally aired but holy crap is this insane.  A classic moment in television.  Conan interviewing Hunter S. Thompson is about as crazy as it gets, but Conan and Hunter pounding whiskey at Owl Farm and shooting fully automatic assault riffles sky rockets this one into complete insanity.  Right around 2:50 shit gets really weird.  Conan doesn’t even really get a word in during the whole interview.

“One of the strangest guests I’ve probably had on the show was the legendary author and creator of gonzo journalism, Hunter S. Thompson,” O’Brien said as an introduction to a re-airing of the now-legendary interview. “Hunter Thompson cultivated a reputation not only for his erratic behavior but for producing some of the best writing of the last century, including Fear and Loathing in Las Vegas.” Noting that the good doctor refused to come to the studio for an interview, O’Brien explained the author agreed to shoot a remote segment “and I met him on a farm in upstate New York to shoot guns and drink hard liquor.” Adding, “He probably expected me to say that’s not going to happen … we brought a camera crew, and here’s what happened.”