One of the mainstays of the entertainment business is talk shows. Sometimes, it can improve the relationships between hosts and their guests, and vice versa.
Some talk show hosts get along perfectly with certain celebrities, while others have, to put it mildly, had rocky relationships with some celebrities. Harry Styles, for example, frequently makes appearances on The Late Late Show with James Corden. He even took over as host when Corden had to skip episodes due to his child’s birthday.
However, there are still instances where we have to cringe at talk show hosts who made celebrities feel awkward. With their flirtatious or blatantly intrusive questions, we can’t decide who’s cringing more – us, or the celebrities in these interviews. These interviews turned out to be such a mess, and we can’t look away.
In this list, we’ll be looking at various situations from talk shows where the host put their famous interviewees, like Angelina Jolie, Joaquin Phoenix, and Jennifer Aniston, in a clearly uncomfortable situation.
#1 David Letterman & Angelina Jolie “Late Night with David Letterman” (1982-93)
In an interview with Angelina Jolie, David Letterman asked increasingly intrusive questions that she was obviously finding difficult to answer. He brought up her relationship status almost immediately after making a remark about how she “smelling nice.” As Letterman pressed her for more information, she hesitated before speaking. During this interview, it was obvious that Jolie was not having fun. On this list, we’ve seen some of Letterman’s dubious behavior toward his female guests before, and we will see it again. And sadly, this embarrassing Angelina Jolie interview was no different.
#2 David Letterman & Jennifer Aniston “Late Show with David Letterman” (1993-2015)
Jennifer Aniston talked to David Letterman in 1998 when she was at the peak of her “Friends” fame. The interview began normally with standard questions and other things. After asking for forgiveness, Letterman leaned in unreasonably close to Aniston and took a strand of her hair in his mouth. This is when things took a slightly sudden weird turn and s he was fortunately given a napkin to wipe it off. Then he said she scared him because she yelled a little bit as he was doing the inappropriate thing. Simply bizarre Aniston began to stumble over her words as the interview went on and was clearly nervous.
#3 David Letterman & Michael Richards “Late Show with David Letterman” (1993-2015)
Michael Richards made headlines in 2006 by launching into a bizarre racial tirade in a comedy club. Richards was brought in via satellite when Jerry Seinfeld showed up on “Late Show” shortly after the incident to make a formal apology. Seinfeld stood by his pal, but the other studiogoers didn’t. The audience started laughing as soon as Richards entered the room. Seinfeld himself asked everyone to stop laughing after his word choice, which included referring to African Americans as “Afro-Americans,” became a target of ridicule. Many thought this was a poor use of air time because uncomfortable laughter also filled the awkward silence in Richard’s speech.
#4 David Letterman & Uma Thurman “Late Show with David Letterman” (1993-2015)
Uma Thurman was a guest on David Letterman’s “Late Show” in the 1990s. The interview began as usual, with Dave cracking his customary lighthearted jokes. However, as Letterman appeared to be attempting to flirt with Thurman, things started to become increasingly awkward. In between talking about her upcoming movie and asking her about the ages of the men she has dated, he slips in a question about his own age. Uma then nervously laughs and tries to change the subject. He finishes by praising her ears and referring to her as a “lovely piece of work.”
#5 Graham Norton & Cara Delevingne “Comic Relief: Red Nose Day” (2017)
In 2017, when discussing the “mile-high club,” the host of “Graham Norton’s Big Chat Live” focused on Cara Delevingne during the Red Nose Day telethon. He simply stated it rather than asking her if she had done it on a plane before. She mentioned her father being in the crowd right away, looking embarrassed. Despite acknowledging this, Norton persisted in his line of inquiry, ignoring the father issue in his pursuit of comedic gold. Although Delevingne doesn’t have a great reputation as an interview subject, it’s difficult not to support her in this case.
#6 Jay Leno & Judith Light “The Tonight Show with Jay Leno” (1992-2009; 2010-14)
Source: Celebrity Videos
The “Who’s the Boss?” star Judith Light spoke with Jay Leno in 1995. Since the interview got off to a rocky start, we doubt that it would be permitted to continue today. The interviewer immediately brought up a previous discussion about a movie where Light appeared nude. Then, he appeared to be trying to bring up the subject of her nudity on screen constantly. Light ended up showing Leno how cable-tv nude shoots operate as a result of him getting way too close to her. He unbuttoned her shirt while holding her hands behind her back. Clearly looking for help, she requested to go to commercial, and even fellow guest David Spade appeared visibly uncomfortable.
#7 Jimmy Fallon & Roger Waters “Late Night with Jimmy Fallon” (2009-14)
Fallon is a huge Pink Floyd fan, so it makes sense that he was excited to speak with Roger Waters on “Late Night.” The conversation inevitably turned to Syd Barrett, a former band member who quit and was said to have battled severe mental illnesses, including schizophrenia. When talking about the late Barrett, Waters became noticeably emotional and her tone changed to seriousness. After that, Fallon joked about Barrett interrupting a Pink Floyd song by calling him “a bald man with a toothbrush in his mouth.” Waters clarified the situation, making sure to inform Fallon that it wasn’t a humorous tale and that everything was actually very tragic.
#8 Jimmy Kimmel & Joaquin Phoenix “Jimmy Kimmel Live!” (2003-)
Jimmy Kimmel brought up Joaquin Phoenix’s childhood interest in breakdancing during an interview with him. Phoenix appeared surprised and may have not expected the topic to be brought up. Phoenix continued to answer Kimmel’s questions, despite appearing visibly frustrated while doing so; he even said it wasn’t funny. Phoenix was shocked by Kimmel with some “bonus” footage from “Joker,” which made the actor come off as a bit of a diva and added salt to the already sensitive wound. Because of this, Phoenix was abruptly forced to apologize for his behavior on set, which made him feel very uncomfortable.
#9 Jimmy Kimmel & Katherine Langford “Jimmy Kimmel Live!” (2003-)
Source: Headline Planet
Australian actress Katherine Langford, who appeared in “13 Reasons Why,” was being interviewed by Kimmel. The host asked the actress where she learned to speak English—specifically, what he called “regular English,” or what they speak in America—after asking the usual questions. Despite the fact that the question was obviously very flawed, she handled it with grace. Perhaps the unease could have been avoided if Kimmel had asked about accents rather than rephrasing his query. He could have avoided the verbal flub or failed wisecrack, whichever it may have been, by admitting that he erred in speaking.
#10 Stephen Colbert & Kristen Stewart “The Late Show with Stephen Colbert” (2015-)
Everything was going smoothly when Kristen Stewart appeared on Stephen Colbert’s show, but then technology interfered. Colbert briefly stopped the conversation before “readingjusting” Stewart’s microphone, which was causing audio problems because it was rubbing against a necklace she was wearing. Stewart was obviously not a fan of Colbert’s proximity to her chest area as he repositioned the microphone. Colbert carried on with the interview as usual without seeming phased by anything that had happened.