30 Most Awkward Celebrity Interviews of All Time

Chuvic - February 19, 2023
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Are you a fan of celebrity interviews? It’s the rare chance to get up close and personal with our favorite stars and see a glimpse of their true selves, outside of the characters they play on the big and small screens.

But let’s be real; not all interviews are created equal. Some are downright inspiring and heartwarming, while others make us cringe with secondhand embarrassment. And then there are those that spark outrage and controversy.

Take, for example, the time when Samuel Jackson was mistaken for another actor. Umm, awkward much? And who could forget when Katie Couric asked a transgender model about her “private parts” on national television in 2014? Seriously, what was she thinking?

But what about those interviews from yesteryear that, upon reflection, are just downright unacceptable? Some of them went unnoticed at the time, but now have people shaking their heads in disbelief.

Bruce Willis Was Hostile to His Interviewer Just Because He didn’t Want to be There

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Bruce Willis is known for his iconic roles in action-packed movies, but it seems like he was not in the mood for an interview during his press tour for Red 2. In an awkward interview, Willis seemed disinterested and almost hostile towards the interviewer, bringing the interview to an uncomfortable halt. At one point, he even stated that selling the movie was not acting, which implies that he was not having any fun during the press tour. While it’s unclear if he was just having a bad day or if he was tired of promoting the film, Willis’ lack of enthusiasm made for an awkward and uncomfortable interview for all involved. It’s a reminder that sometimes even Hollywood stars have their off days.

Mel Gibson Calls His Interviewer an A$$hole

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The interview between Mel Gibson and Dean Richards is one that many viewers won’t soon forget. Despite maintaining his composure for most of the interview, it’s clear that the actor was feeling the heat when the topic of his past controversies was brought up. Gibson’s guarded responses and defensive demeanor hinted at the underlying tension in the conversation. However, the most memorable part of the interview came when Gibson thought the cameras had stopped rolling. In a moment of candid frustration, he called Richards an a**hole. The comment was caught on camera and quickly went viral, leaving many wondering what other unfiltered thoughts celebrities might have about their interviewers. The awkward exchange was a reminder that even the most seasoned actors can find themselves in uncomfortable situations, and that the pressures of the media spotlight can sometimes cause cracks to show.

Barbara Walters Called Dolly Parton a “Hillbilly”

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Dolly Parton is no stranger to interviews, but her sit-down with Barbara Walters had some uncomfortable moments. Walters, known for her hard-hitting questions, asked Parton about her upbringing, and the way she dressed, and even questioned if people thought she was a joke. She even went as far as calling Dolly Parton a hillbilly! These questions could have easily thrown anyone off their game, but Parton handled them with grace and poise, showing why she’s considered a legend in the entertainment industry. Despite the awkward moments, the interview flowed smoothly, showcasing Parton’s ability to handle tough situations and maintain her composure.

Robert Downey Jr’s Interview Walk Out

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During a press tour for Avengers: Age of Ultron, Robert Downey Jr. encountered an uncomfortable line of questioning during an interview with Krishnan Guru-Murthy. Instead of focusing on the film, the reporter delved into the actor’s past, prompting Downey Jr. to walk out of the interview. Downey Jr. had no interest in rehashing his personal struggles with drugs and alcohol and made it clear that the interview was veering off-topic. He eventually cut off the line of questioning and left, commenting on the way out that the interview was becoming too much like a personal expose. Downey Jr. was determined to keep the conversation focused on his work in the Marvel franchise and his role as Iron Man.

Samuel Jackson Was Mistaken for Another Actor

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Oh boy, have you heard about the time a reporter mixed up two of Hollywood’s biggest stars? It was an absolute disaster and had everyone in stitches! During an interview, the reporter mistakenly asked Samuel L. Jackson about a Super Bowl commercial that Laurence Fishburne had starred in. At first, Jackson looked puzzled before realizing what had happened. He couldn’t believe it and yelled out, “I’m not Laurence Fishburne!” But it didn’t end there – Jackson couldn’t resist giving the host a hard time about his mistake, making for a hilarious and unforgettable interview. He even pointed out, “We may all be black and famous, but we don’t all look alike!” Let’s just say, the host learned a valuable lesson that day!

Ben Affleck’s Interview with a Canadian-French Journalist

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Let me tell you about one wild and crazy interview that actor Ben Affleck had back in 2004! While promoting his movie “Jersey Girl” on “Box Office,” he spoke with a French-Canadian journalist named Anne-Marie Losique who, get this, sat in his lap for the entire interview. Can you imagine?

Affleck didn’t hold back either, suggesting that Losique take off her shirt, mocking French accents, and even making comments about her “firm breasts.” Yikes! But that’s not even the worst of it.

But wait, there’s more! Losique later defended the interview, saying that it was taken out of context and that they had “many interviews like that.” She even aired the full, unedited interview because she thought it was “kind of fun.” Apparently, their on-camera antics were a hit in Quebec, with people loving the clips of Affleck’s outrageous behavior.

Vin Diesel Reacted to Charlize Theron’s Comment on His Kiss

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Vin Diesel is known for his tough-guy persona on and off-screen, but even he can get flustered in interviews. During an appearance on The Ellen Show, the actor was confronted with a comment made by his Fast & Furious 8 co-star Charlize Theron, who claimed that his kissing skills were lacking. Diesel was visibly taken aback by the comment and even stood up to ask the audience if he looked like a “dead fish.”

Despite the awkwardness of the situation, Diesel was able to laugh it off and joked that he needed to “work on his moves” before his next on-screen kiss. The audience seemed to be on his side, cheering and clapping in support. While it may have been an uncomfortable moment for Diesel, it’s a reminder that even tough guys like him can be caught off guard in interviews.

Jane Fonda Was Uncomfortable that She Was Asked About Her Plastic Surgery

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In a 2017 interview on Megyn Kelly Today, Jane Fonda was visibly uncomfortable when the topic of her plastic surgery came up. Kelly asked Fonda about her decision to have work done, to which Fonda responded with visible annoyance. She redirected the conversation back to the Netflix film she was promoting, Our Souls at Night. The awkward exchange left the studio audience cringing as Fonda shut down the conversation about her personal life. After the interview aired, Fonda expressed her dissatisfaction with the line of questioning and went on to say that she wished she had responded differently in the moment. The incident serves as a reminder to interviewers to be respectful and mindful of the topics they bring up, especially when it comes to a celebrity’s personal life.

Tom Hardy Was Asked About His Sexuality

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Tom Hardy, the talented actor known for his roles in films such as “Mad Max: Fury Road” and “The Dark Knight Rises,” has had his fair share of media attention over the years. However, one interview in particular stands out as being particularly awkward. During an interview with a reporter from a LGBT publication, Hardy was asked about his sexuality. In response, he shut down the question, stating that his private life was not up for discussion and that it had no bearing on his work as an actor. The exchange left the interviewer and many fans feeling uncomfortable, as it is often seen as important to have LGBTQ+ representation in the entertainment industry. Despite the awkwardness of the moment, Hardy’s decision to set a boundary around his personal life was a reminder that celebrities are entitled to privacy, even in the public eye.

Rihanna Was Asked What She’s Looking for in Her “Next Man”

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During a 2014 fragrance launch event, reporters were eager to ask the superstar all sorts of juicy questions, including what she was looking for in a man. But when one bold journalist posed the question, Rihanna’s response was anything but typical.

First, she leaned in to make sure she heard correctly. Then, with a sassy swerve, she declared, “I’m not looking for a man. Let’s start there.” Boom! The room went silent as Rihanna shut down any notions of romance right then and there. It was a fierce and unapologetic move, but would we expect anything less from this iconic queen?

Meg Ryan’s Uncomfortable Interview

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Meg Ryan’s interview with Michael Parkinson on the BBC was certainly an uncomfortable one. Parkinson seemed to question Ryan’s comfort level with being a star, and she struggled to remember what she had previously said. The interview quickly turned awkward, with Parkinson pushing Ryan about why she would continue in a career she was uncomfortable with. Ryan seemed to grow more and more uncomfortable with the questioning, and eventually asked to wrap it up.

Lindsay Lohan Cried When Asked About Her Plans About Getting into Rehab

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Get ready for some drama! Lindsay Lohan’s 2013 appearance on “Late Show” was supposed to be about promoting “Scary Movie 5,” but things quickly took a turn when Letterman brought up her upcoming stint in rehab. The host began by complimenting Lohan’s appearance but then fired off questions about her supposed thieving habits and financial responsibility.

But the real focus of the interview was Lohan’s upcoming rehab stint. Letterman grilled her on when she was going, why she was going, and how long she planned to stay. The pressure was too much for the actress, and she couldn’t hold back her tears.

Desperate to steer the conversation in a more positive direction, Lohan pleaded with Letterman to move on and keep things light. But the damage had been done, and the cringe-worthy interview will go down in history as one of the most uncomfortable moments in late-night TV.

Ariana Grande Called Out a Sexist Question

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Ariana Grande is no stranger to speaking her mind, especially when it comes to issues that matter to her. So, it’s no surprise that during an interview for KPWR radio, she didn’t shy away from calling out a sexist question.

When asked if she’d rather give up using her phone or stop wearing makeup, Ariana Grande was quick to fire back, “Is that what y’all think girls have trouble choosing between?” The host then pressed on and asked her if she could really go without her phone, to which she replied, “For many hours.”

However, the host didn’t stop there and took it upon himself to offer unsolicited advice, saying, “Ladies, learn!” Ariana was having none of it and snapped back, “Boys, learn!”

Diane Sawyer Defended the Person who Threatened to Shoot Britney Spears

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In 2003, journalist Diane Sawyer sat down with Britney Spears for an interview that made headlines for all the wrong reasons. In a montage of her most misogynistic interviews in “Framing Britney Spears,” Sawyer is shown asking the pop star whether she likes her own voice and focusing on her wardrobe choices instead of her talent.

But that’s not all. Sawyer also brought up a shocking comment made by Kendel Ehrlich, the then-governor of Maryland’s wife, who said she would shoot Britney Spears if she had the chance. And instead of calling out this outrageous threat, Sawyer seemingly defended Ehrlich!

To make matters worse, Sawyer went on to grill Spears about her breakup with Justin Timberlake, suggesting that the young singer was responsible for his heartbreak. It all became too much for Britney, who finally broke down in tears and asked for a break.

After the “Framing Britney Spears” documentary aired in 2021, many fans demanded an apology from Sawyer for her disrespectful and harmful interview.

Jesse Eisenberg was just Plain Rude

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Jesse Eisenberg, known for his roles in The Social Network and Now You See Me, has had a reputation for being a bit of a rude dude. But in this particular interview, he takes it to a whole new level.

When interviewer Romina Puga asks him a question, he responds by comparing her to the infamous comedian Carrot Top. And that’s just the beginning! He goes on to tell her not to cry during the interview, but to save it for after so it doesn’t look like his fault. Ouch!

Throughout the entire conversation, there’s a mix of playful banter and straight-up insults. And it all comes to a head when Romina finally tells Jesse, “You’re such a jerk.” The whole thing is a catastrophe, but it’s definitely one of those trainwrecks you just can’t look away from.

Cara Delevingne’s British Humor on Good Day Sacramento

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Cara Delevingne is no stranger to the entertainment industry, having worked as both a model and an actress. However, when she appeared on Good Day Sacramento to promote her role in the film Paper Towns, things quickly took a turn for the awkward. The hosts mispronounced her name, calling her “Carla” instead of “Cara,” and continued to make cringe-worthy comments throughout the interview.

When they suggested that Cara seemed less enthusiastic than in a previous interview, she pushed back, telling them that wasn’t the case. The hosts then suggested she take a nap or drink a Red Bull to perk up. It was an uncomfortable moment for both Cara and those watching the interview.

Cara later defended herself, saying that some people just don’t understand the British sense of humor. While it’s important for interviewers to keep things light and engaging, it’s equally important to be respectful and avoid making their guests uncomfortable.

Interviewer Kept Asking Quentin Tarantino about the Violence in His Movies

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Quentin Tarantino is an iconic director known for his incredible films that are famous for their graphic violence. After a long career, Tarantino has often been asked about the effect of his movies on people and whether they promote real-life violence. When Krishnan Guru-Murthy decided to delve into this topic during an interview, Tarantino was quick to shut it down.

Guru-Murthy seemed determined to press the issue, despite Tarantino’s clear discomfort with the subject. Tarantino responded by warning the interviewer that he won’t be pushed into answering questions he doesn’t want to. He made it clear that he won’t be bullied or manipulated, and that he has every right to steer the conversation in a direction he’s comfortable with.

It’s clear that Tarantino is a fiercely independent artist who won’t be swayed by external pressures. He’s determined to stay true to his vision and won’t let anyone interfere with his creative process. It’s no wonder that he’s become a cinematic legend, thanks to his uncompromising attitude and innovative approach to filmmaking.

Dakota Johnson’s Awkward Convo with Her Mom

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Get ready for some red carpet drama! At the 2015 Academy Awards, Dakota Johnson and her mother, the iconic actress Melanie Griffith, stepped in front of the cameras for a live interview. But things went south quickly when the interviewer referred to Dakota as Melanie’s “little girl.”

The situation didn’t get any better when the reporter asked Melanie if she had seen Dakota’s provocative film, 50 Shades of Grey. Melanie responded with a simple “no,” while Dakota looked visibly uncomfortable. But it was Dakota’s response that took the interview from awkward to cringe-worthy.

After her mother’s response, Dakota snapped, “Alright! You don’t have to see it,” and looked hurt as she spoke. The tension between the mother-daughter duo was palpable, and it seemed like the interviewer had hit a nerve with her question. Despite the awkward moment, Dakota maintained her composure and continued to promote her film.

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Jessica Simpson’s Awkward Interview with Ellen

Jessica Simpson’s recent appearance on The Ellen DeGeneres Show left both viewers and the host herself in a state of confusion. As soon as the interview started, Jessica caught everyone off guard by announcing that she got an IUD to prevent any pregnancies. The revelation set the tone for an interview that would be anything but typical.

When Ellen asked about the activities that Jessica and her husband enjoy doing together, the singer struggled to come up with an answer, leaving the audience to wonder if they even have shared hobbies. It was a rare moment where the usually bubbly and effervescent Jessica seemed to be at a loss for words.

During the interview, Jessica struggled to answer simple questions, like how long she and her husband have been married and what activities they enjoy doing together. At one point, Ellen even turned to the camera, unsure how to react. While some have speculated that Jessica may have been nervous or under the influence of something, the interview serves as a reminder that even the most successful and glamorous celebrities can have moments of vulnerability and uncertainty.

Jim Carrey’s Eccentricity Shines Through in Awkward Red Carpet Interview

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Jim Carrey is undoubtedly one of the most talented actors of his generation. He has made audiences laugh and cry with his performances in films like “The Truman Show,” “Eternal Sunshine of the Spotless Mind,” and “Man on the Moon.” However, in recent years, he has also gained a reputation for being a bit eccentric. This was on full display during a red carpet interview with E! News reporter Catt Sadler at the Harper’s Bazaar Icons Party.

As Sadler tried to ask Carrey a few simple questions, he responded with answers that left her feeling uncomfortable and unsure of how to react. When asked why he decided to attend the event, Carrey responded with a bizarre statement: “There’s no meaning to any of this, so I wanted to find the most meaningless thing that I could come to and join.” He went on to say that he didn’t believe in personalities and that he didn’t believe Sadler existed. It was a strange and uncomfortable exchange that left Sadler staring at the camera, unsure of what to do next.

Mila Kunis Stands Up for Justin Timberlake During Awkward Press Conference in Moscow

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Mila Kunis and Justin Timberlake’s press tour for their movie “Friends with Benefits” brought them to Moscow for a press conference. While answering questions in her native language, Russian, Mila couldn’t help but stand up for her co-star when a reporter asked him a strange question.

The reporter asked why Timberlake transitioned from show business to film, and why it wasn’t enough for him. In response, Kunis asked the reporter, “What would you rather have him do?” and then added, “Why are you here?” to imply that everyone has the right to choose their own path and it’s no one else’s business.

Scarlett Johansson Shuts Down Inappropriate Interview Question

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Actress Scarlett Johansson is no stranger to weird or inappropriate questions in interviews. During one press conference for the movie Avengers, she was asked a question that crossed the line. The interviewer asked whether she was able to wear undergarments while in her character’s costume.

Johansson, clearly taken aback by the question, responded with a hint of frustration, saying, “You’re like the fifth person that’s asked me that.” She then questioned why it had become acceptable to ask such personal questions during interviews. When the interviewer asked if it was inappropriate, Johansson made it clear that it was, in fact, inappropriate to ask such a question.

Sharon Stone and Sebastian Stan Flirt Shamelessly During Interview

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An interview with actress Sharon Stone and Avengers actor Sebastian Stan may not have gone according to plan, but it certainly made for an entertaining and flirtatious exchange. The actor, who has been a longtime admirer of Stone, decided to take his shot and flirt with her during the interview.

In his native language of Romanian, Stan shamelessly tried to pick up Stone, while James Corden, the host of the show, egged him on. At one point, Stone even asked Stan if he would bite her neck, in reference to Dracula, and he eagerly obliged.

While the interview may not have gone off the rails, the chemistry between Stone and Stan was undeniable. The playful banter and shameless flirting made for a fun and lighthearted exchange that left the audience and even the host, James Corden, amused.

Lauren Conrad’s Quick-Witted Response to Inappropriate Question

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Reality star and businesswoman Lauren Conrad found herself in an awkward situation during a Q&A in 2014. During the session, which was designed for fans to ask Conrad questions that had been prepared by producers, the star was asked a highly inappropriate question that caught her off guard.

The question read, “What’s your favorite position?” Conrad was clearly flustered by the inappropriate query, and took a few seconds to gather her thoughts. But instead of ignoring the question or becoming upset, Conrad responded with a quick-witted answer that showed off her clever sense of humor.

Daniel Radcliffe’s Awkward Interview with Miriam Margoyles

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Daniel Radcliffe is best known for playing the iconic role of Harry Potter in the successful film franchise. However, in a recent interview, Radcliffe found himself in an awkward situation with Miriam Margoyles, a fellow actor from the Harry Potter films.

During the interview, Margoyles, who played Professor Sprout in the movies, made a comment that left Radcliffe feeling uncomfortable. She pointed out that Radcliffe’s voice had changed significantly since he first started playing the role of Harry Potter at the young age of 11.

While this observation may seem like an innocent comment, it clearly made Radcliffe feel uncomfortable. He awkwardly laughed it off, saying, “It’s the elephant in the room, isn’t it?” Despite the uncomfortable moment, Radcliffe handled the situation with grace and humor, making light of the situation.

Weird Interview with Intoxicated Mark Wahlberg

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Mark Wahlberg is no stranger to entertaining audiences with his comedic acting, but his appearance on The Graham Norton Show in 2013 left everyone in shock. The talk show, which featured fellow guests, Sarah Silverman and Michael Fassbender, quickly turned awkward as Wahlberg seemed to have had one too many drinks backstage. The actor slurred his speech and talked over the other guests, creating an uncomfortable atmosphere. But that wasn’t the worst of it. Wahlberg climbed onto host Graham Norton’s lap and began stroking his chest, almost giving him a “purple nurple.”

While the audience appeared to be amused, it was an awkward moment that left Norton and other guests surprised and uncomfortable. It also served as a reminder that allowing guests to drink backstage may not always lead to a great interview. Nonetheless, Wahlberg’s antics on the show have become a memorable moment for viewers and fans.

Helena Bonham Carter’s Funny Moment with Rihanna

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During a 2018 appearance on The Graham Norton Show, the cast of “Ocean’s 8” was asked if they had been invited to the MET Gala. Everyone except Helena Bonham Carter had received an invitation, leaving her as the odd one out. Rihanna, who was also a guest on the show, jokingly blamed it on Bonham Carter’s fashion choices, which caused the audience to erupt in laughter. While the moment may have been slightly awkward, Helena took it in stride and was a good sport about the situation. This incident serves as a reminder that even the biggest stars can experience moments of discomfort and awkwardness during interviews, but it’s how they handle those moments that truly shows their character.

Kourtney Kardashian Froze on TV When Asked About Kim’s Traumatic Experience

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In 2016, Kourtney Kardashian was interviewed for an Australian television show when she was asked about her sister Kim’s traumatic experience of being robbed at gunpoint in Paris. The question seemed to catch Kourtney off guard, and she froze for a few moments, staring into the screen with a blank expression. The hosts of the show were left wondering if they had lost connection or if Kourtney was simply ignoring the question. Eventually, Kourtney found her words and proceeded to answer the question. It’s understandable that the topic would be sensitive for the Kardashian family, and Kourtney’s initial reaction shows how difficult it can be to talk about such traumatic experiences in a public setting. While some may criticize Kourtney’s response, it’s important to remember that everyone processes trauma differently, and it can take time to find the right words to express one’s feelings.

Kiera Knightly was Described as “Worn Out” by her Interviewer

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During a press tour for the movie “The Imitation Game,” Keira Knightley and Benedict Cumberbatch were exhausted from the non-stop interviews. One interviewer thought it was a good idea to mention to Keira that she looked tired, which is definitely not the best thing to say to a hard-working actress. Benedict, being the chivalrous gentleman he is, immediately jumped to her defense and put the rude interviewer in their place. “That’s not a nice thing to say to one of the most beautiful women on the planet,” he said. And just when you thought it couldn’t get any better, Keira chimed in and dropped an epic F-bomb. Talk about a power duo!

Carmen Carrera was asked about her Private Parts

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It was supposed to be an uplifting segment showcasing the story of transgender model Carmen Carrera on Katie Couric’s talk show in 2014. But the interview took a nosedive when Couric went from asking about Carrera’s modeling career to prying into her personal life.

With cameras rolling and a live audience watching, Couric dropped the bombshell: “Your private parts are different now, aren’t they?” Carrera was taken aback, and shushed Couric, “I don’t want to talk about it because it’s really personal.”

The conversation took a sharp turn, and Carrera tried to steer it back to the positive aspects of her life post-transition. But the damage had been done. Couric’s intrusive line of questioning resulted in intense backlash, with many calling out her insensitivity towards the transgender community.

Even Laverne Cox, who appeared on the show after Carrera, spoke out against Couric, explaining that focusing on someone’s transition instead of their everyday life objectifies them.

These cringe-worthy moments during celebrity interviews just go to show that even the most famous and composed stars can become flustered or taken aback by unexpected questions, awkward moments, or simply miscommunications. From uncomfortable questions and awkward silences to technical difficulties and cultural differences, these celebrities have found themselves in some of the most uncomfortable interviews in history. However, their reactions vary from losing their cool to remaining calm and collected, proving that how one handles a difficult situation can truly make or break the interview. While it may be entertaining for us to watch, it’s important to remember that celebrities are humans too, and they can experience just as much discomfort as the rest of us.

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