It’s been ten years since The Colbert Report debuted, but while we still all get to visit with the real Stephen Colbert nightly over on CBS, it’s not the same and we miss the old him a little. Sure, he could be combative, rude, ill-informed, misogynistic, etc., etc., etc., but it was all a part of the joke and everyone got that… right? Well, maybe not. As Colbert’s old show grew in popularity, many guests came prepared for battle when they sat down across from the host, but some guests of the Comedy Central show simply could not handle what Colbert was throwing at them.
In honor of the 10th anniversary of The Colbert Report‘s 2005 premiere, here are a few hillariously awkward on-air encounters.
Barney Frank
As part of Colbert’s “Better Know a District” segment in 2005, then-Massachusetts 4th district representative Barney Frank sat down for what he very obviously felt was an intolerable interview. Dubbed by the comedian as “flamboyantly liberal,” the Democrat grew increasingly unamused during the conversation.
Colbert began a thinly veiled line of questioning about his left-handedness, then, eventually, started actually questioning the politician about his sexuality. Before requesting Frank list other gay public figures (so he wouldn’t be unprepared in the future), Colbert told the Harvard grad he’s overweight.
Further proof Frank was definitely not in on the joke? In a later interview, he referred to Colbert as an “assh*le.” Shots. Fired.
Robert F. Kennedy Jr.
RFK Jr. was brought on the show to defend/support his 2006 Rolling Stone article that purported former president George W. Bush stole the 2004 presidential election from Kerry. What’s awkward here, other than Colbert’s attempts to spin some of RFK Jr.’s comments as racist, was the mention of the attorney’s late uncle, president John F. Kennedy.
“Which was easier – for a Bush to steal Ohio in 2004 or for your uncle to steal Illinois in 1960?” Colbert asked. RFK Jr. paused and the audience’s very nervous laughter made for a noticeable silence.
The question prompted RFK Jr. to bring up longstanding rumors that dead people’s identities were used to cast votes in Illinois’ Cook County at the time. He explained that Kennedy would have won with or without Illinois, before ultimately acknowledging the presence of some cheating in the campaign. Colbert’s response? “Well, I accept your apology.”
Dan Brown
Author Dan Brown, who many will know as the creative mind behind smash hit The Da Vinci Code, visited Colbert in 2013 to promote his new book, Inferno. For those who aren’t familiar, Brown’s (best-selling) novels often tackle pillars and symbols of Christianity. “What I ask in The Da Vinci Code is, ‘what does it mean for Christianity if Christ literally was not the son of God?'” explained Brown during the appearance.
Colbert, who said he reads Brown’s books because he enjoys being filled with “rage,” started the interview with guns blazing: “You’ve got a thing for the Catholic church … are you gunning for the Catholic church?” Momentarily, the life visibly left Brown’s eyes – it was obviously a question he’d faced before, and one he wasn’t ready to face again.
Diane Keaton
An exchange so uncomfortable it spurned headlines like “Diane Keaton Gets Weird And Super Awkward On Colbert.” Whether she was attempting to go head-to-head with Colbert’s character’s antagonistic nature or not, Keaton left even the host flustered when she (jokingly) accused him of being a “sexual pervert” during her 2012 appearance.
After stepping on stage to promote her memoir, the actress immediately informed Colbert she wouldn’t be supporting his then-presidential bid. She fired back at any of his attempts to change the subject, and convincingly informed him she’d be filing “sexual harassment charges” for the hug they’d shared backstage.
Morrissey
The word “irritated” best sums up Morrissey’s 2012 interview (despite a couple chuckles). First, Colbert brought up Britain’s royal family, whom the rocker had clear disdain for, then he prodded Morrissey about a reunion of The Smiths. When Colbert mentioned the artist’s former bandmate Johnny Marr (who was responsible for The Smiths dismantling in the late ’80s), and urged him to cash in and reunite, the cheery singer replied, “Not everybody is a fat old slag, not everybody is.”
Then, to add insult to injury, the host made a joke about a pig committing suicide after listening to the staunch vegetarian’s music. “You shouldn’t laugh at that,” Morrissey told the audience.
Philip Mudd
Former FBI Senior Intelligence Advisor Philip Mudd stopped by in 2013 to promote his book Take Down: Inside the Hunt for Al Qaeda and, essentially, had absolutely no interest in dealing with Colbert or his antics.
Not once did he crack a smile, even while delivering lines like “TV turns your brain into cotton candy.” Mudd told the comedian he hadn’t turned a TV on in 20 years, which made the appearance on a television show all the more interesting.
“We’re not on Broadway right now,” Colbert retorted. “TV is selling your book right now. Want to amend that in any way?”
He didn’t.
Bart Ehrman
It’s amazing that Bart Ehrman would subject himself to Colbert a second time, because he seemed so completely at odds with the comedian’s character. While promoting his book Jesus, Interrupted in 2009, the author attempted to detail the “contradictions” in the Bible, attempted being the key word.
His range of comebacks to Colbert’s insults (which included calling Ehrman antisemitic) ranged from “yea” to “right.” The American New Testament scholar barely held up in the religious tete-a-tete over the paternity of Jesus.