When Jennifer 8 Lee was prepping for her 2008 interview on The Colbert Report, she didn’t know what to expect. A friend who wrote for The Daily Show gave the author some good advice: Don’t try to out-funny Stephen Colbert; “just be calm and roll with the weirdness.”
Over the past nine years, Colbert—in character as a fact-free conservative pundit—has commanded a powerful perch at his round interview table, keeping guests off kilter four nights a week. In especially brilliant moments, he has asked tougher questions than real journalists. After all, Colbert’s the guy who asked Robert F. Kennedy Jr.—appearing on the show to discuss his 2006 Rolling Stone piece, “Was the 2004 Election Stolen?”—if it was easier for George W. Bush to steal the 2004 election, or for Kennedy’s uncle, John F. Kennedy, to steal the 1960 presidential election. Colbert also asked Zero Dark Thirty director Kathryn Bigelow if she believed that the CIA purposely misled her to make torture techniques seem worthwhile.
Truthiness be told, Colbert might be best remembered for the cringe-inducing awkwardness of so many of his Colbert Report interviews. He often seemed to delight in the moment when an unsuspecting interview subject would get a telltale look of cornered confusion. That confused, annoyed look was definitely more prevalent in the early Report years—but not exclusive to them. We’ve rounded up some of Colbert’s most awkward interviews for you to watch, squirm, and laugh through all over again. READ FULL STORY