Top 10 Celebrity Interviews That Made Everyone Uncomfortable

And the Academy Award for the most awkward red carpet interview goes to… Hugh Grant! The British actor raised eyebrows at the 2023 Oscars when he stopped for a brief chat with model and TV presenter Ashley Graham. Grant quickly made it painfully clear he’d rather be anywhere else, offering blunt, almost comically short answers to every question. Even when Graham tried to inject some enthusiasm by asking about his experience filming “Glass Onion,’ Grant shut it down with a reply so lifeless, it could have been the subject of its own murder mystery. Once the interview hit the internet, it went viral, with some criticising Grant for being rude, while others chalked it up to classic British humor.

Comedian Bobcat Goldthwait is famous for his wild antics on stage. And when he was invited on “The Tonight Show with Jay Leno” in 1994, he brought some of them along. During the interview, Goldthwait, who was apparently furious over the cancellation of “The Arsenio Hall Show,” decided to stage a protest by setting the guest chair on fire. It was a stunt that could have gone horribly wrong, but thankfully, Leno doused the flames with his water and then made Goldthwait sit in the now-charred seat. Whatever point the comedian was trying to make got lost in the smoke. Instead, he ended up getting charged with a misdemeanor, fined $2,700 and forced to film a series of fire-safety PSAs.

For an interviewer, breaking juicy celebrity news must be thrilling. But you’d think a seasoned talk show host would know when to exercise a little restraint. Back in 2008, Mariah Carey appeared on “The Ellen DeGeneres Show” amid rumors that she was pregnant. In reality, she had been dealing with fertility issues and wasn’t ready to go public with the news yet. That didn’t stop DeGeneres who, despite Carey’s glaring discomfort, pulled out a bottle of champagne and dared her to drink. Carey then faked a sip, which pretty much confirmed the news and led to DeGeneres screaming in delight. Looking back, the singer described the moment as “extremely uncomfortable,” made even worse by the heartbreaking fact that she miscarried soon after.

It doesn’t speak well of you if you’re an entertainment reporter and you can’t tell two very famous actors apart… especially when they look nothing alike. During a 2014 interview with Samuel L. Jackson, KTLA anchor Sam Rubin asked him about his recent Super Bowl ad. There was just one problem; Jackson hadn’t been in one. Rubin had actually mistaken him for Laurence Fishburne, who reprised his role from “The Matrix” in a commercial that year. Once the blunder was out there, there was no taking it back. Morgan Freeman wasted no time calling Rubin out, reminding him that not all black actors look alike. Of course, Rubin was clearly embarrassed and quickly offered an apology to Danny Glover.

Sometimes, an awkward interview is the host or reporter’s fault. Other times, like in this instance, it’s the celebrity who is to blame. In 2016, Brazilian YouTuber Carol Moreira was simply doing her job, interviewing Vin Diesel when he visited the country. But the actor had other plans. Diesel spent most of the interview shamelessly flirting, repeatedly commenting on her looks while ignoring almost all of her questions. Moreira looked uncomfortable, yet she remained professional and tried to get the interview back on track, to no avail. At one point, Diesel even declared her “too sexy” to continue and suggested they ditch the interview for a date. It was too fast, too furious and way too frustrating to watch.

There are bad interviews, and then there’s whatever happened when Jennifer Aniston appeared on the “Late Show with David Letterman” in 1998. Aniston was there to promote her film “The Object of My Affection,” but somehow became the object of a truly bizarre moment. As she casually chatted, Letterman crept up behind her and sucked on a strand of her hair. He then handed her a tissue to wipe off. What purpose did this weird act serve, you might ask. Well, we’ll never know, because Letterman brushed past it and simply forged ahead. Years later, in a 2013 interview with Lindsay Lohan, Letterman proved that old habits die hard, as he relentlessly pressed the actress about her time in rehab despite her obvious discomfort (xref).

Ever since he rose to fame in the early 2000s, Kanye West has made so many inflammatory remarks that it would be easier to list the few that weren’t controversial. One of his most shocking comments came during a 2018 interview at the TMZ headquarters. When asked about his support for Donald Trump, West veered into a rant in which he seemed to suggest that slavery was a choice. His remarks left the room in stunned silence. Eventually, TMZ host Van Lathan spoke up, voicing out the disappointment that everyone was feeling and urging West to do better. Clearly, Lathan’s words went in one ear and out the other, as West has racked up plenty more controversies since then.

Almost every actor in Hollywood would do anything to earn $1.8 million per episode on a TV show. Charlie Sheen had that and threw it all away when he picked an unnecessary fight with Chuck Lorre, the creator of “Two and a Half Men,” which got him fired. Amid the scandal, Sheen appeared on “Good Morning America,” where he attempted to assure the public that he was unfazed by his dismissal. However, his erratic behavior during the interview, where he famously declared himself “bi-winning” and claimed to have cured himself of substance use disorder, only made people more concerned. We weren’t the only ones who found this interview uncomfortable; even Sheen himself later admitted that it was “a little bit cringeable.”

Britney Spears’ private life has long been a subject of public scrutiny. Back in 2003, when the pop singer was just 21, she sat down for an interview with veteran broadcaster Diane Sawyer. What should have been a regular conversation quickly turned into an interrogation, as Sawyer grilled Spears about her high-profile split from Justin Timberlake, essentially blaming her for it. As if that wasn’t bad enough, Sawyer then appeared to justify a statement from the then-First Lady of Maryland, who had openly said she wanted to attack Spears for being a bad influence. At one point, the singer felt overwhelmed and broke down in tears, but that did little to stop Sawyer from pressing on.

Throughout his career, R. Kelly has been dogged by allegations of sexual assault and predatory behavior. He managed to escape conviction in 2008, but when these allegations resurfaced with the 2019 docuseries “Surviving R. Kelly,” there was no slipping away. Shortly after he was criminally charged in Illinois, Kelly appeared in a contentious interview with Gayle King. For 80 exhausting minutes, he insisted he was innocent of the allegations. He even put on a grand show, pounding his chest and yelling at the cameras. If Kelly was aiming for sympathy, he completely missed the mark, as his aggressive display only made him look unhinged. The evidence against the singer continued to mount and he was eventually sentenced to a combined 31-year term.


What celebrity interview left a bad taste in your mouth? Let us know in the comments below.