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Top 10 Times Talk Show Hosts Made Celebrities Uncomfortable

For most of us, awkward moments have been embedded in our memories for years since. We see them when we close our eyes to sleep, so imagine how celebrities who lived through them must have felt, all the while on camera. Awkward, isn’t it?
It is undeniable that those awkward on-camera moments involve the talk show host being inappropriate to the guests. Talk show hosts often abuse their position of authority. This can take many forms, such as not allowing guests personal space or asking invasive questions. Surprisingly, several well-known and well-liked hosts have crossed the line.
People have been scouring the talk show archives for other awkward moments after word leaked that talk show host veteran David Letterman is a creep. As a result, it appears that it is not just Letterman who was improper with his guests: inappropriate behaviors and questions are widespread among numerous TV hosts.
From improper flirting to broaching delicate subjects to making fun of their guests, here are 1- times when talk show hosts were making their guests feel uncomfortable.

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

Source: dailymail

This one, in particular, is rather embarrassing. When the issue of the "mile-high club" surfaced during his "Graham Norton's Big Chat Live" part of Comic Relief's Red Nose Day telethon event in 2017, the host questioned Delevingne. He didn't ask her if she'd done it previously on an aircraft, but simply stated it. She seemed ashamed and mentioned her father being in the audience. Norton accepted this, but continued the line of questioning, brushing over the father issue in his pursuit of on-camera comedy. Delevingne's record as an interviewee isn't great, but most people would side with her on this one.

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

Source: neptunepinkfloyd

Fallon is a huge Pink Floyd fan, so he was naturally ecstatic to be interviewing Roger Waters on "Late Night." The conversation inevitably turned to Syd Barrett, a previous member of the band who left and was reported to have suffered from severe mental health problems, including schizophrenia. When mentioning the late Barrett, Waters became visibly sad and serious. Fallon then joked about Barrett disrupting a Pink Floyd performance, referring to him as "a bald man with a toothbrush in his mouth." Waters clarified the statement, assuring Fallon that it wasn't a funny story and that the entire event was quite sad.

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

Source: britannica

Jay Leno interviewed Judith Light of "Who's the Boss?" fame in 1995. Things started off awkwardly, and to be honest, we don't think an interview like this would be permitted today. The host instantly brought up a previous interview in which Light appeared naked in a film. He then seemed to be continuously trying to bring up the subject of her onscreen nudity. As a result of getting too close to her, Light ended up demonstrating to Leno how cable-tv nude shots work. He then unbuttoned her top while holding her hands behind her back. She wanted to go to commercial, evidently in need of assistance, and fellow guest David Spade showed obvious discomfort.

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

Source: YouTube

David Letterman interviewed Jennifer Aniston at the height of her "Friends" stardom in 1998. The interview began properly, with standard questions and so forth. It then took a strange turn when Letterman prayed for forgiveness, then went in close to Aniston and grabbed a strand of her hair with his mouth. (She was later given a tissue to wipe her hair.) He then claimed she scared him since she let out a small yell as he was engaging in his inappropriate behavior. Aniston was noticeably anxious during the rest of the interview, fumbling over her sentences.

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

Source: Youtube

David Letterman's questions to Angelina Jolie were increasingly… invasive, and she was plainly battling to keep her cool. He almost immediately commented on her "smelling wonderful" and inquired about her marital status. Letterman urged her for more answers, and she paused with her words. During the interview, it was evident that Jolie was not having a good time. Evidently, we've seen some of Letterman's dubious behavior toward his female guests before, and we'll see it again. And, sadly, Angelina Jolie's cringeworthy interview was no exception.

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

Source: YouTube | Jimmy Kimmel Live

Jimmy Kimmel brought up Joaquin Phoenix's youthful break-dancing obsession during an interview with him. Phoenix appeared surprised as if he hadn't expected the question to come up. Kimmel persisted, with Phoenix answering his questions - but noticeably irritated; Phoenix even warned him it wasn't something to joke about. To add salt to the wound, Kimmel shocked Phoenix with some "extra" footage from "Joker," which made the actor look like a diva. This resulted in a very uncomfortable Phoenix being forced to apologize for his behavior on stage. We can only presume he was relieved to see the end of this interview.

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

Source: YouTube | The Late Show with Stephen Colbert

A minor technological issue might sometimes cause agony. Everything was going smoothly when Stephen Colbert had Kristen Stewart on his show... until technical issues got in the way. Colbert interrupted the talk for a moment before "readjusting" Stewart's microphone, which was striking a necklace she was wearing and producing audio problems. Colbert got a little too close to Stewart's chest area when readjusting the mic, and she was definitely not pleased. Colbert seemed unfazed by the incident and seamlessly went on with the rest of the interview.

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

Source: Youtube

This event probably made everyone uncomfortable. Michael Richards made headlines in 2006 after launching into a weird racist tirade in a comedy club. When Jerry Seinfeld appeared on "Late Show" shortly after the incident, he invited Richards to apologize publicly via satellite. Seinfeld stood by his pal, but the rest of the cast did not. When Richards appeared, the audience began to chuckle almost immediately. His use of terms, such as referring to African Americans as "Afro-Americans," drew widespread mockery, to the point where Seinfeld himself urged everyone to stop laughing. Many people believed that the unpleasant silences in Richard's speech were also filled with uncomfortable laughter and that this was a poor use of air time.

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

Source: YouTube | Jimmy Kimmel Live

It's difficult to tell whether the following is a jest or an intentional mocking. Even the visitor is perplexed. Kimmel was interviewing Australian actress Katherine Langford from "13 Reasons Why." The interview began in the usual manner, but the host then asked the actress where she learned to speak English - that is, "standard English," or the language used in America. She addressed it gracefully, although the question was clearly wrong. Perhaps Kimmel's concern could have been avoided if he had rephrased his question and asked about accents instead. Or he could have admitted he misspoke, which would have saved him from the verbal gaffe or missed wisecrack, whatever it was.

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

Source: Youtube

David Letterman interviewed Uma Thurman on "Late Show" in the mid-'90s, and it began normally, with Dave delivering his typical light-hearted quips. However, things became increasingly uncomfortable when Letterman appeared to be flirting with Thurman. He mentions her next project before shifting gears and asking her the ages of the men she's dated, inserting his own age into the mix. Uma, for her part, attempts to change the subject while nervously chuckling. He finishes by complimenting her ears and referring to her as a "beautiful piece of work."
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