Top 10 Times Talk Show Hosts Made Celebrities Uncomfortable
Top 10 Times Talk Show Hosts Made Celebrities Uncomfortable

Top 10 Times Talk Show Hosts Made Celebrities Uncomfortable

VOICE OVER: Rebecca Brayton WRITTEN BY: Nancy Roberge-Renaud
We're still cringing about all the times talk show hosts made celebrities uncomfortable. For this list, we'll be looking at various moments from talk shows where the host created a visibly uncomfortable situation for their famous interviewee. Our countdown includes “Jimmy Kimmel Live!,” “The Late Show with David Letterman,” “The Tonight Show with Jay Leno,” and more!

Awkward... Welcome to MsMojo, and today we’ll be counting down our picks for the Top 10 Times Talk Shows Hosts Made Celebrities Uncomfortable.

For this list, we’ll be looking at various moments from talk shows where the host created a visibly uncomfortable situation for their famous interviewee. Get ready to cringe.

#10: David Letterman & Uma Thurman
“Late Show with David Letterman” (1993-2015)

In the mid-’90s, David Letterman interviewed Uma Thurman on “Late Show”, and it started out normally, with Dave making his usual light-hearted jokes. Yet things got gradually uncomfortable, as Letterman seemed to be attempting to flirt with Thurman. He speaks of her upcoming film, yet makes a shift into asking her the ages of the men she’s dated, slipping his own age into the mix. Uma, in turn, tries to change the subject while nervously laughing. He tops it off with complimenting her ears and calling her a “lovely piece of work.”

#9: Jimmy Kimmel & Katherine Langford
“Jimmy Kimmel Live!” (2003-)

It’s hard to tell if this next one is a joke or a serious intellectual lapse. Even the guest appears confused. Kimmel was interviewing Katherine Langford from “13 Reasons Why,” who is an actress from Australia. The questioning started the usual way, but then the host asked the actress where she learned to speak English - that is, what he called “regular English,” or what they speak in America. She handled it with grace, yet the question was clearly greatly flawed. Perhaps the unease could have been prevented had Kimmel rephrased his question, and asked about accents instead. Or he could have acknowledged that he misspoke, which would have saved him from the verbal flub or failed wisecrack, whatever it may have been.

#8: David Letterman & Michael Richards
“Late Show with David Letterman” (1993-2015)

This one is guilty of making everyone uncomfortable. In 2006, Michael Richards gained infamy by going off on a bizarre racist tirade in a comedy club. When Jerry Seinfeld appeared on “Late Show” shortly after the incident, he brought in Richards via satellite to apologize publicly. Seinfeld supported his friend, but those in the studio did not. When Richards appeared, the audience almost immediately could be heard laughing. His choice of words, including referring to African Americans as “Afro-Americans”, served as a source of ridicule to the point that Seinfeld himself told everyone to stop laughing. The awkward silences in Richard’s speech were also filled with uncomfortable laughter, and many felt this was not an effective use of air time.

#7: Stephen Colbert & Kristen Stewart
“The Late Show with Stephen Colbert” (2015-)

Sometimes discomfort can be caused by a simple technical difficulty. When Stephen Colbert had Kristen Stewart on his show, everything was going swimmingly… until technology got in the way. Colbert cut off the chatter for a moment, and proceeded to “readjust” Stewart’s microphone, which was hitting a necklace she was wearing and causing audio issues. Colbert got a little close to Stewart’s chest area as he readjusted the mic, and she clearly wasn’t a fan of that. Colbert seemed unphased by the entire thing, and segwayed into the rest of the interview with ease.

#6: Jimmy Kimmel & Joaquin Phoenix
“Jimmy Kimmel Live!” (2003-)

In an interview with Joaquin Phoenix, Jimmy Kimmel brought up Joaquin Phoenix’s childhood break-dancing hobby. Phoenix seemed taken aback, perhaps not expecting the subject to come up. Kimmel pressed on, however, with Phoenix answering his questions - albeit visibly vexed while doing so; Phoenix even told him it wasn’t something to laugh about. To pour salt on the already sensitive wound, Kimmel surprised Phoenix with some “bonus” footage from “Joker,” which made the actor seem like kind of a diva. This led to a very uncomfortable Phoenix suddenly being made to apologize for his behavior on set. We can only assume he was really happy to see this interview come to a close.

#5: David Letterman & Angelina Jolie
“Late Night with David Letterman” (1982-93)

In an interview with Angelina Jolie, David Letterman’s questions became increasingly… mmmm let’s say invasive, and she was clearly struggling to maintain her composure. He almost immediately commented on her “smelling nice,” and brought up her relationship status. She hesitated with her words, as Letterman pressed her for more answers. It became clear that Jolie was not enjoying herself during this interview. We’ve seen some of Letterman’s questionable behavior towards his female guests before on this list and we’ll see it again. And unfortunately, this cringey Angelina Jolie interview was no exception.

#4: Graham Norton & Cara Delevingne
“Comic Relief: Red Nose Day” (2017)

This one is extra cringy. During his “Graham Norton's Big Chat Live” segment of Comic Relief’s Red Nose Day telethon event in 2017, the host zeroed in on Delevingne when the topic of the “mile-high club” arose. He didn’t quite ask her if she’d done it on a plane before, but rather stated it. She immediately appeared embarrassed, and mentioned her father being in the crowd. Norton acknowledged this, yet pursued the line of questioning, brushing the dad issue aside in the quest for comedy gold. Delevingne doesn’t have such a great reputation as an interviewee, but it’s hard not to take her side on this one.

#3: Jay Leno & Judith Light
“The Tonight Show with Jay Leno” (1992-2009; 2010-14)

In 1995, Jay Leno spoke with Judith Light, of “Who’s the Boss?” fame. Things started off awkwardly, and to be honest, we can’t see an interview like this being allowed to take place today. The host immediately brought up a prior interview, in which they discussed a film where Light appeared nude. He then seemed to constantly be looking to raise the topic of her onscreen nudity. This somehow led to Light showing Leno how cable-tv nude shoots work, as he got way too close to her. He then held her hands behind her back and unbuttoned her shirt. She asked to go to commercial, clearly crying out for help, with fellow guest David Spade even showing obvious discomfort.

#2: Jimmy Fallon & Roger Waters
“Late Night with Jimmy Fallon” (2009-14)

Fallon is a big fan of Pink Floyd, and was understandably excited to be interviewing Roger Waters on “Late Night.” The subject inevitably turned to Syd Barrett, a former member of the band who left and was rumored to have suffered from some serious mental health issues, namely schizophrenia. Waters was noticeably emotional when discussing the late Barrett, and took on a serious tone. Fallon then laughingly brought up a story about Barrett interrupting a Pink Floyd recording, referring to him as “a bald man with a toothbrush in his mouth”. Waters cleared up the story, making sure to tell Fallon that it wasn’t a funny tale, and that the entire situation was very sad.

Before we unveil our top pick, here are a few honorable mentions.

Conan O’Brien & Nicole Scherzinger
“Conan” (2010-)

Jimmy Kimmel & Markiplier
“Jimmy Kimmel Live!” (2003-)

Ellen DeGeneres & Bill Gates
“The Ellen DeGeneres Show” (2003-)

David Letterman & Justin Bieber
“Late Show with David Letterman” (1993-2015)

Chelsea Handler & Harry Styles
“Chelsea” (2016-17)

#1: David Letterman & Jennifer Aniston
“Late Show with David Letterman” (1993-2015)

In 1998, David Letterman talked to Jennifer Aniston at the height of her “Friends” fame. The interview started out normally, with typical questions and such. It then took a bit of a sudden weird turn, as Letterman asked for forgiveness, then leaned in ridiculously close to Aniston and took a strand of her hair in his mouth. (She was thankfully handed a napkin to clean it off). He then claimed she scared him, as she let out a slight yell when he was performing his inappropriate action. Just… bizarre. When the interview continued, Aniston was visibly nervous and stumbling over her words from that point forward.