The Worst Stephen Colbert Interview Moments Fans Are Still Watching In 2024

Over the years, there have been many highly memorable late-night talk show hosts. In the modern era, Stephen Colbert has become one of the richest talk show hosts according to reports that he has a truly impressive fortune. Since Stephen has spent the majority of his career working as a talk show host, there is no doubt that his late-night TV career allowed him to make millions.

Given Stephen's success as a talk show host, some fans may assume that his interviews rarely go wrong. However, the truth is that Stephen has conducted a surprising number of incredibly awkward interviews over the years.

10 Eminem

The Interview Was Awkward Because Stephen Asked Eminem Bizarre Questions

Between hosting The Colbert Report and The Late Show with Stephen Colbert, Stephen Colbert didn't have a talk show for a while. During that era, Stephen interviewed Eminem for a little-seen public access show called Monroe, Michigan.

An interview that obviously was intentionally awkward, Stephen acted completely out of touch and disinterested in Eminem. While it was clear that Stephen and Eminem were both trying to be awkward, their so-called interview was really uncomfortable to watch. The dry humor Stephen was known for at the time really didn't mix well with the always standoffish way that Eminem carries himself during interviews.

9 Natalie Portman

Was Awkward Because Natalie Portman Seemed Uncomfortable While Talking About Her Former Friend

When Natalie Portman appeared on The Late Show with Stephen Colbert, the host brought up that she graduated from Harvard. While discussing that topic, the fact that Donald Trump's son-in-law Jared Kushner at the same time and they were "friendly" came up. While Natalie was very happy to insult Jared, as she called him a super-villain, she kept looking away from Stephen as she notably seemed uncomfortable with the conversation.

8 Elizabeth Warren

Was Awkward Because Stephen Colbert Questioned Whether Elizabeth Warren's Job Should Exist

When Stephen Colbert interviewed Elizabeth Warren in 2022, he asked her a question about the government.

"What if we just get rid of The Senate?"

As a Senator, Elizabeth laughed at Stephen's suggestion only for him to make it very clear that he wasn't joking. "I'm 100% serious here." Elizabeth then looked at Stephen with one of the most uncomfortable and unsure expressions in talk show history. After Stephen explained his argument, the interview ultimately got back on track as they had a substantive conversation. However, that moment was so awkward that Men's Health included the interview as a part of their May 2023 article about the most awkward moments in talk show history.

7 Sarah McDaniel

Was Awkward Because Of How Stephen Colbert Reacted To Sarah McDaniel's Revealing Outfit

When Sarah McDaniel appeared on The Late Show with Stephen Colbert, she wore an obviously low-cut dress she repeatedly adjusted. At one point in the interview, Stephen drew attention to that by holding something over her chest as Sarah laughed felt awkwardly. In response, Stephen's conduct has been praised by some. However, when Sarah once rewatched that moment when she appeared on one of Hasan Piker's streams, she revealed how awful she felt at that moment. Knowing how Sarah felt makes it hard to watch that moment.

"Yeah it was an extremely awkward, probably the worst moment of my life."

6 T.J. Miller

Was Awkward Because Of T.J. Miller's Antics

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When T.J. Miller went on The Late Show with Stephen Colbert, he brought some props with him. The interview became uncomfortable for viewers once T.J. pulled the first one of his props out.

Early on in the interview, T.J. called himself out for hypocrisy. While doing that, T.J. retrieved an egg from his pocket and smashed it on top of his head while stating he had "egg on his face". As the interview progressed, T.J. used skeleton hands to caress Stephen's face for several seconds before the interview came to a merciful end.

4 Casey Affleck

Was Awkward Because Things Instantly Became Tense After Stephen Colbert Called Out Casey Affleck's Outfit

When Casey Affleck went on The Late Show with Stephen Colbert in 2016, he was relatively dressed down. From the moment the interview began, Stephen called Casey out for not being dressed up. The discussion over Casey's clothes lasted so long that Casey eventually asked "How long are we going to talk about this?" and Stephen jokingly suggested they should fight.

While the beginning of the interview was enough of a reason for this interview to belong on this list, there is more to it than that. Casey went on the show to promote his movie at the time, Triple 9. As a February 2016 Sharp Magazine article about how awkward the interview was pointed out, Stephen made things even more awkward. Stephen did that by telling Casey he started watching Triple 9 and then turned it off.

“I’ve only seen an hour and ten minutes of it, because I had to stop and help my son with a science experiment. That’s a true story.”

3 Rose McGowan

Was Awkward Because Rose McGowan's Comments Confused The Audience

When he interviewed her in February 2018, Stephen Colbert quickly brought up how comfortable Rose McGowan is with uncomfortable situations. As the interview progressed, the viewers became uncomfortable, as a Vox article from the time outlined how strange the interview was. After all, Rose often ignored Stephen's questions to discuss whatever she wanted to and the audience went silent as they seemed to have no idea how to respond.

2 Bill Burr

Was Awkward Because Stephen Colbert Didn't Embrace Bill Burr's Humor

Widely considered to be one of the best comedians of his generation, Bill Burr is known for how hilarious he is when he expresses his frustrations. Bill is also known for not holding back when he expresses his opinion. For those reasons, it made sense when Stephen introduced Bill as being known for his "rage-filled humor".

The thing that didn't make any sense, however, was that Stephen didn't seem prepared for Bill's style of humor. Throughout the interview, there were several times when Bill went off on a rant, as he always does during interviews. Instead of playing along, Stephen went silent several times during the interview, which made the interview very awkward to watch. As an article from The Things pointed out, many fans called Stephen out about how he handled the interview.

1 Kristen Stewart

Was Awkward Because Stephen Got Too Close And Seemed To Annoy Kristen

After Stephen Colbert interviewed Kristen Stewart in 2017, a fan put together a 3-minute compilation of all the times she seemed annoyed by him. The most obvious example of that came when Stephen reached out and moved a necklace Kristen was wearing. At the time, Stephen explained that he moved the necklace because the chain was hitting the show's microphone. Still, Kristen seemed taken aback by Stephen getting so close and that was very awkward to see for viewers.