Talk show interviews don’t always go as planned, if they are planned at all, and the potential for an awkward exchange between the host and their guests is pretty huge.
Sometimes, the unpredictability makes for great entertainment. But for this list, we’re looking at different moments from talk shows where the host made their guests very uncomfortable.
Ellen DeGeneres and Justin Bieber
In 2015, Justin Bieber was invited on Ellen DeGeneres’ talk show. And the comedian quickly brought up a photo the paparazzi took of him in Bora Bora where he wasn’t wearing any clothes.
Talking about it was awkward enough, but DeGeneres also showed the photo on the screen behind him during their conversation.
Stephen Colbert and Tiffany Haddish
During a visit to Stephen Colbert’s talk show, Tiffany Haddish offered him some solid tips on how to treat his growing white beard. He claimed his wife was his beard’s biggest critic because of the unpleasant texture.
So Haddish told him to condition it and Colbert just looked at her mortified and said, “I’ll keep that in mind.” But when someone like Haddish offers you grooming advice, you should take it.
Conan O’Brien and Maria Menounos
Maria Menounos talked to Conan O’Brien about her workout regimen and how firm her abs were. Then she asked him to punch her abs and also returned the favor. Afterwards, she rubbed his arm and told him that he just got hotter. Then she started laughing awkwardly, which shocked O’Brien.
He pointed out that her laughter broke him out of the trance she put him under, and she tried to pretend like she wasn’t bothered by the comment.
Stephen Colbert and Sarah McDaniels
While Playboy model Sarah McDaniels was doing an interview on “The Late Show With Stephen Colbert,” she kept lifting her strapless dress up. And then Colbert asked her, “Can I get you some duct tape?” But McDaniels soldiered on.
Then Colbert got a paper towel from his desk and placed it over her cleavage, which was undoubtedly very awkward for the model.
David Letterman and Uma Thurman
In the 1990s, David Letterman appeared to be flirting with Uma Thurman during an interview. He started out with lighthearted jokes but then moved on to asking her the ages of the men’s she’s dated.
He then slipped his own age into the mix forcing her to laugh it off nervously while trying to change the subject. The whole situation made viewers die from second-hand embarrassment.
Jimmy Fallon and Katherine Langford
Jimmy Fallon was interviewing Australian actress Katherine Langford from “13 Reasons Why” when he suddenly asked her where she learned to speak what he called "regular English."
While she answered it gracefully, Kimmel could have used the phrase American accent as opposed to regular English.
Jimmy Kimmel and Markiplier with MissesMae
Jimmy Kimmel was interviewing YouTubers Markiplier and MissesMae, but he made distasteful comments after Markiplier explained how being an influential gaming figure helps him make a difference.
Then MissesMae tried changing the subject by talking about how her mom reacted to virtual reality and Kimmel made an inappropriate comment about her mom’s screaming.
Stephen Colbert and Kristen Stewart
During an interview with actress Kristen Stewart, Stephen Colbert tried to adjust her microphone which was hitting a necklace she was wearing and causing audio issues.
But he got a little too close to the star’s chest area and she was obviously made uncomfortable by the encounter.
Jimmy Kimmel and Joaquin Phoenix
Jimmy Kimmel brought up Joaquin Phoenix’s childhood breakdancing hobby and the actor was clearly embarrassed.
But Kimmel continued asking him questions and Phoenix kept on answering even though he was obviously cringing about sharing his old hobby with the audience.
David Letterman and Angelina Jolie
During an interview with Angelina Jolie, David Letterman’s questions got a little invasive when he commented on how nice she smelled and then mentioned her relationship status.
He continued to press her for more information on her personal life. At that point, it was clear that Jolie wasn’t enjoying the interview.
Graham Norton and Cara Delevingne
While appearing on the “Comic Relief: Red Nose Day” special, Cara Delevingne got very uncomfortable when the topic of the mile-high club came up. Graham Norton didn’t directly ask her if she had ever been intimate on a plane before but sort of stated it.
And it was obvious that she was embarrassed before she mentioned that her dad was in the audience.
Jay Leno and Judith Light
Jay Leno was interviewing “Who’s the Boss” star Judith Light and brought up a previous interview where they discussed a scene in which she did not have clothes on. He continued raising the topic of other onscreen scenes in which she showed lots of skin.
This led to Light showing him how nude scenes worked, but the host got too close. Then he held her hands behind her back and unbuttoned her shirt. She asked the host to cut to commercial as she was obviously uncomfortable.
Jimmy Fallon and Roger Waters
Jimmy Fallon was interviewing Roger Waters from the band Pink Floyd when he brought up Waters' former bandmate Syd Barrett, who reportedly suffered from mental health issues.
Waters was visibly emotional, but then Fallon brought up a funny story of Barrett interrupting a Pink Floyd recording, referring to him as the bald man with a toothbrush. Waters explained that it wasn’t a funny story and that the situation was sad.
Ellen DeGeneres and Bill Gates
During an appearance on Ellen DeGeneres’ talk show, Bill Gates played a game called Bill’s Grocery Bill. In it, the Microsoft co-founder had to guess the price of certain items.
For one bag of pizza rolls he guessed $22 and the audience kept shouting at him to go lower. Even Ellen was pointing down with her finger and it was obvious that Gates was uncomfortable.
Conan O’Brien and Nicole Scherzinger
While appearing on “Conan,” Nicole Scherzinger spoke about how she met Simon Cowell when she suddenly noticed that Conan O’Brien was busy staring at her cleavage.
But she quickly turned the tables on him by telling the talk show host to focus on her face. And at the end, O’Brien was the one who was red in the face.
David Letterman and Justin Bieber
David Letterman noticed something on Justin Bieber’s arm and asked him if he had a new tattoo, to which the pop star said yes. Then Letterman groaned and asked, “Oh, God! How many do you have?” And Bieber awkwardly replied that he had a couple.
So, Letterman told him to assure him that this was the last one. And the singer said maybe, but he was very disturbed.
David Letterman and Jennifer Aniston
In 1998, David Letterman apologized in advanced. Then he leaned very close to Jennifer Aniston and put a string of her hair in his mouth.
She was later handed a napkin to clean her hair and pointed out that the audience was horrified but Letterman claimed the scene would be taken out during editing.
Megyn Kelly and Jane Fonda
During “Megyn Kelly Today,” Megyn Kelly’s conversation with Jane Fonda took a turn for the worse when the host brought up the actress’ plastic surgery.
Although Kelly said she looked amazing, Fonda was obviously bothered and tried to stir the conversation back to her movie, but it was obvious that she wanted the interview to end.
Kelly Osbourne and Rosie Perez
During a conversation on “The View” with actress Rosie Perez, Kelly Osbourne claimed that if President Trump kicked every Latino out of the United States, then no one would be around to clean his toilet.
And Perez told Osbourne that Latinos are not the only people who do that. And Osbourne explained that she didn’t mean it that way but the damage was already done.
Larry King and Jerry Seinfeld
During “Larry King Live,” Larry King asked Jerry Seinfeld about his sitcom “Seinfeld,” which had come to an end. But things got weird when he asked the actor if he gave it up or if the show was canceled.
Seinfeld got quiet for a second and then he clapped back and questioned King’s professionalism and preparedness.
Jimmy Kimmel and Margaret Qualley
During an interview with actress Margaret Qualley, Jimmy Kimmel pointed out that her feet were featured heavily in a Quentin Tarantino movie. Then he went on to point out that her character, who was a member of the Manson family, had armpit hair and he asked her if it was her real hair.
She claimed she grew it out and he then asked her if she shampooed and conditioned it to which she laughed uncomfortably.
Conan O’Brien and Jennifer Garner
Jennifer Garner felt pretty embarrassed after she appeared on Conan O’Brien and told him that “snuck” wasn’t really a word.
So, rather than continuing to argue with her, he simply pulled out a dictionary from his desk, looked up the word and proved to her that she was wrong.
Oprah and Drew Brees
During an interview with New Orleans Saints quarterback Drew Brees, Oprah noticed something on his face and asked him, “Who just kissed you?”
Then she tried to wipe the substance off his face, not realizing that it was actually Brees' birthmark, which was a pretty awkward moment for him.
Tyra Banks and Robert Pattinson
On her talk show, Tyra Banks made British actor Robert Pattinson very uncomfortable during an interview promoting the first “Twilight” film.
Not only did she pretend to have a British accent, which was terrible, but she also asked him to bite her. Fortunately, he was a good sport and did it anyway.
Oprah and Bristol Palin
In 2010, Oprah invited Sarah and Bristol Palin to her show and asked the younger Palin if she felt that abstinence until marriage was an unrealistic goal. Palin replied and said she didn’t think it was unrealistic.
Then Oprah replied, “good luck to you.” Meanwhile, her mom strained a smile but it was obvious that she didn’t like someone asking her daughter about this topic.