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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.

Barney Frank

In October 2005, Massachusetts Democrat Barney Frank became The Colbert Report‘s second-ever “Better Know a District” subject. In the interview, Colbert pretends not to know Frank is gay, asks him about being openly left-handed, and queries if Frank’s “wife” thinks he should lose a little weight. You can tell Frank isn’t quite sure what to make of Colbert just yet. “Ignorance does not offend me,” he says at one point.

Barbara Lee

Things got really weird last month with Rep. Barbara Lee (D-Calif.), who represents an Oakland district. Colbert hit on race, sex, lesbians, and propositioned the even-tempered congresswoman after a stadium wave that went on a bit too long.

Philip Mudd

When Colbert interviewed Mudd, a former deputy director of the CIA’s counter-terrorist center and a senior FBI intelligence advisor, in September 2013, the interview turned awkwardly testy when Mudd revealed he doesn’t own a TV. In fact, he said he decided 20 years ago to dump the medium because it “turns your brain into cotton candy.” Colbert’s response: “We’re not on Broadway right now. TV is selling your book right now. You want to amend that in any way?” The testiness continued when Colbert questioned Mudd about “enhanced interrogation.”

Diane Keaton

Colbert’s interview with Keaton was awkward with a capital A, but not so much because of Colbert. Keaton, appearing in May 2012 to promote the paperback release of her memoir, seemed uncomfortable from the start. If she was trying to be funny when she told Colbert she wouldn’t vote for him for president and was planning to bring sexual harassment charges against him, well… she wasn’t.

Eric Schmidt

In September 2010, Colbert dove right into data-mining and privacy issues with the Google CEO, telling Schmidt that his controversial remark about young adults changing their names to escape their online pasts was a good idea. “It was a joke,” Schmidt replied. “And it just wasn’t very good.”

Richard Branson

Branson may be the only guest to have thrown a cup of water at Colbert. While on the show to promote Virgin Airlines in August 2007, he doused the host after a gritted-teeth interview in which Branson complained he wasn’t given enough time to plug his airline. Colbert is handed a water bottle, and a bit of a water fight ensues.

Bonus: John Kerry

Colbert offered this rare glimpse of the advice he gives some guests in the clip of this pre-show meeting, taped by Talking Points Memo TV in 2007. As Colbert tells then-Senator John Kerry, now Secretary of State: “You know that I’m in character, that I’m an idiot… I’m willfully ignorant of what we’re going to talk about. So disabuse me of my ignorance.” Bet some of the people on this list would’ve liked to have a similar pre-interview chat with Colbert.

The Colbert Report
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