As Conan O’Brien says goodbye to his Late Night this week, the talk-show host has been taking a look back at his favorite moments from his show’s 16-season run. Last night, he payed homage to Rolling Stone royalty by re-airing his “unusual day” with literary legend Hunter S. Thompson. “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 the clip. “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.”

O’Brien then aired footage of the pair downing giant glasses of whiskey and taking aim at a variety of targets that include a cardboard cut-out of Thompson, a promotional poster for Thompson’s The Proud Highway, copies of the aforementioned hard-covered book, as well as an NBC Peacock and a stuffed ape from FAO Schwarz. Thompson suggests they grab a propane canister. Did we mention they were shooting automatic machine guns?

For more on Thompson, check out our archives:

• Growing Up Gonzo: Excerpts From the Oral History of Hunter S. Thompson
• Photos: Hunter S. Thompson
• Excerpt: Fear and Loathing in Las Vegas
• Fear and Loathing, Campaign 2004