Every time a celebrity agrees to be interviewed, it has the potential to go one of two ways. The first — a memorable, joyful experience that leaves both the interviewer, the celebrity and the world feeling warm and fuzzy.
The other way? An unforgettable trainwreck that feels majorly uncomfortable to watch, but somehow leaves you unable to actually turn it off. Who could forget the time that a young Britney Spears was reduced to tears by Diane Sawyer, or Meghan and Harry’s Oprah interview that left the Royal family reeling?
While you might assume these kinds of celebrity interviews are quite rare, you’d actually be mistaken. There have been countless instances where either the interviewer or the celebrity has been left with a very, very bad taste in their mouths, and unsurprisingly, they’re a little hard to forget.
From Jennifer Aniston having her hair sucked to Anne Hathaway dodging incredibly sexist Catwoman questions, below we round up the most explosive celebrity interviews of all time.
Jamie Lynn Spears on Good Morning America
Throughout 2021, Britney Spears’ little sister, Jamie Lynn came under fire for her involvement in her old sister’s conservatorship which saw her lose essentially all freedoms. Britney has spoken candidly about the betrayal and torture she faced at the hands of her family, but Jamie Lynn wasn’t going to let the narrative end there.
Instead, she organised an exclusive with Good Morning America where she attempted to redeem herself. She feigned ignorance around the entire conservatorship, saying that she understands “just as little about it then as I do now,” before calling herself her “sister’s biggest supporter.”
She also spoke about her teenage pregnancy, which upset many fans as it lead to the cancellation on popular Nickelodeon show, Zoey 101. Jamie Lynn claims she was pressured by many people, including family members and her management team to make the “issue” disappear, but when she was refused, was sent to a remote cabin with no connection to the outside world.
“It felt like you’re almost like suffocating,” she told the host. “I felt like what was I going to do, I was a kid, and maybe this is in my best interest and maybe this is what I’m supposed to do because of course I don’t want to be, you know, hounded by the paparazzi or the tabloids or allow them to control my narrative. But it felt like I was really being alienated.”
Dakota Johnson on The Ellen DeGeneres Show
The world was in shock when actress Dakota Johnson bravely called out talk-show host Ellen DeGeneres while appearing on her show. During the interview, Ellen accused Dakota of not inviting her to her 30th Birthday party, but she was quickly called out.
“Actually, no. That’s not the truth, Ellen,” Dakota quipped back. “I did invite you and you didn’t come…ask everybody,” she said, before seeking backup from Ellen’s producers. They confirmed that the host had in fact been invited to the celebration but had chosen not to attend — awkward.
This face-off took place back in late 2019 and in the middle of 2021, news began to circulate that Ellen was running a toxic workplace, amongst other damaging accusations (including allegations of sexual misconduct) which lead to her talk-show’s cancellation.
Jordyn Woods on Red Table Talk
At this point, we’re all well aware that monogamy isn’t Tristan Thompson’s thing. But, while he has been notoriously unfaithful to Khloé Kardashian with a slew of different women, nobody suspected that one of them would be Kylie Jenner’s best friend, Jordyn Woods.
Woods and Thompson were said to have been caught kissing at a party, and after that, the rumour quickly escalated to the pair allegedly having sex. Jordyn denies ever sleeping with Tristan but admitted that he had kissed her. It wasn’t long before the longtime bestie to Kylie was completely ousted by the famous family.
A few months later, Jada Pinkett Smith invited Woods on her show Red Table Talk to tell her side of the story. As for why Jordyn wasn’t upfront about what had happened, she claims she was trying to protect Khloé.
“I was trying to protect Khloé’s heart,” she said. “She doesn’t deserve this either. People have even dehumanized her in this situation where they can’t feel for her. And it’s not fair that she has to deal with this either. And the last thing I wanted to do was be that person.”
“I’m not home-wrecker. I would never try to hurt someone’s home, especially someone that I love and someone who has a beautiful daughter. I never was trying to steal someone’s man. I don’t need your situation. I really just hurt so many more people by not telling the truth.”
To this day, the Kardashian’s are still not friends with Jordyn, despite Khloé giving Tristan several more chances to stay faithful to her.
Meghan Markle and Prince Harry on Oprah
Meghan and Harry’s interview with Oprah could not have been more eye-opening and damning for the Royal family.
It started with Meghan revealing that she’d suffered from suicidal thoughts and was not offered any help from ‘The Institution’, later revealing that both she and Harry felt trapped.
“I went to the institution, and I said that I needed to go somewhere to get help, I said I’d never felt this way before… and I was told that I couldn’t, that it wouldn’t be good for the institution.”
In perhaps one of the most explosive revelations, the couple revealed that there were ‘concerns and conversations’ over the colour of their son Archie’s skin.
Madonna and Courtney Love on MTV
Courtney Love and Madonna have never been the best of friends, in fact, they’re downright rivals. No pop culture moment was greater proof of this than the 1995 VMA’s, when the two came to blows on live television.
Madonna was giving an interview, when out of nowhere, a makeup compact flies over the top of her head, skimming her hair. Upon looking down, it seems that Courtney Love is responsible, and she continues to throw a seemingly endless string of makeup compacts at Madonna, while making her way up the stairs toward her.
“Courtney Love’s in dire need of attention right now,” Madonna tells the cameras.
Speaking about people they used Mohave crushes on within the industry, Courtney reveals that she used to fancy Dennis Miller, before turning to Madonna and saying:
“You don’t even do rock stars anymore! You—as Michael Stipe would say—dip into the population…”
“Yeah..” Madonna replies, sounding unamused.
Courtney then goes on a long tangent comparing the music business to working in a hospital, before Madonna suggests that she should leave said metaphorical hospital.
“Nah, man I like it in here! Nice clothes… good money,” Courtney replied.
“And lots of available drugs!” Madonna added.
Courtney then tells Madonna that Kurt Cobain compared the two women to one another, telling Courtney that she was the spitting image of Madonna in Truth Or Dare. This comment sent Madonna over the edge, who couldn’t have been more unimpressed by the comparison, and had to be taken away by her people before the situation escalated.
Princess Diana on the BBC
Martin Bashir’s interview with Princess Diana in 1995 was a huge scoop for the network, as a Royal family member had never spoken so candidly with a media outlet before.
During the interview, Diana admitted to having an affair, battling an eating disorder and spoke about the personal impact of Charles and Camilla’s relationship.
The interview proved to be even more controversial when it was revealed that the BBC had actually faked documents in order to persuade Diana to give the interview.
Ben Affleck on Box Office
Ben Affleck has been haunted by one interview in particular, which seems to keep rearing its head several decades later. Back in 2004 while promoting his film Jersey Girl, Affleck spoke with a French-Canadian journalist named Anne-Marie Losique, who sat in his lap for the duration of the interview.
Throughout their conversation, he made highly inappropriate comments about her body, suggesting that she take off her shirt and commenting on how ‘firm’ her breasts were.
During the #MeToo movement in 2017, Hilarie Burton claimed Affleck groped her breast during a 2003 appearance on MTV’s TRL (which would have been just a year prior to this interview).
Not long after these claims, Ben’s interview with Losique began re-circulating, with many questioning his behaviour towards woman. Losique actually defended Ben, saying she conducted interviews like this all the time and hadn’t felt uncomfortable in the actor’s presence. She did however acknowledge that it has not aged well.
Anne Hathaway on Extra
Anne Hathaway was forced to endure an uncomfortable string of questions from Jerry Penacoli while doing press for The Dark Knight Rises.
The reporter repeatedly made comments about Hathaway’s body, asking if it was difficult for her to get into ‘perfect shape’ for the role, and commenting that her figure looked great.
“It wasn’t about being in perfect shape,” the actress replied. “It was about being able to do the stunts and the fighting perfectly.”
The reporter persisted with asking questions related to her diet and exercise routine leading up to the film, with Hathaway brushing her regimen off as “boring”.
The interview took a turn when Hathaway flipped his intrusive line of questioning back on him, asking:
“Are you trying to lose weight? What’s the deal, man? You look great,” she said. “No, no seriously. We have to talk about this. What do you want? Are you trying to fit into a catsuit?”
Jennifer Aniston on David Letterman
In one of the most bizarre celebrity interview moments of all time, David Letterman sucked on a piece of Jennifer Aniston’s hair when she appeared on the Late Show in 1998.
“Forgive me if this is rude. I just want to try one thing,” Letterman said, before moving his chair closer to hers and trying to capture a strand of her hair in his mouth.
Aniston, unsurprisingly, was shocked and began squealing and wriggling away, asking Letterman what he was doing. After appearing to suck on a piece of her hair, Aniston wiped off his saliva with a napkin and Letterman carried on with the interview.
Later, he asked her: “You’re still traumatized by that hair deal, aren’t you?”
She told him that she was in fact traumatised, before jokingly asking if someone could carry her offstage.
Britney Spears on Diane Sawyer
At just 21-years-old, Britney Spears appeared on Diane Sawyer, but she wasn’t expecting the interview to take the nasty turn it did, which saw the young singer in tears.
Sawyer began quizzing Spears on the nature of her breakup to Justin Timberlake, accusing her of being unfaithful.
At one point Sawyer reads this quote Spears gave: “But you said, ‘I’ve only slept with one person in my whole life, two years into my relationship with Justin.’ And yet he’s left the impression that you weren’t faithful, that you betrayed the relationship.”
If you were talking to your little sister [Jamie Lynn Spears] now, and the girl who said she was gonna stay a virgin until she got married,” Sawyer says. “Do you still think there’s something to be said for that?”
Then, Sawyer began grilling Spears about a recent magazine shoot which saw her dressed a little more provocatively than usual.
“What happened to your clothes?” Sawyer asks Spears, holding up photos of the singer’s nearly-naked photos. “What is it about?”
“What is it about? It’s about doing a beautiful picture,” Spears replied, unapologetically. “I feel comfortable in my skin,” she says. “I think it’s an okay thing to express yourself.”
Late last year, after finally being freed from her conservatorship, Britney put Diane on blast for the interview. Taking to Instagram in a since-deleted post, she wrote:
“Seriously though… I lived in my apartment for a year and never spoke to anyone… my manager put that woman in my home and made me talk to her on national television and she asked if I had a shopping problem!!! when did I have a problem with shopping ??? When I never left my apartment ???”
“Something I never shared when I had that big break up years ago was that I couldn’t talk afterwards. I never spoke to anyone for a long time …I was in shock. I was a baby …I was almost 22 and didn’t understand … but I f— know now !!!”
Katherine Heigl on Vanity Fair
Knocked Up was arguably a career-defining film for Katherine Heigl, but in an explosive cover interview with Vanity Fair, the actress revealed that she actually hated the movie, which saw her receive significant backlash.
“It was a little sexist,” she told the publication. “It paints the women as shrews, as humorless and uptight, and it paints the men as lovable, goofy, fun-loving guys. It exaggerated the characters, and I had a hard time with it, on some days.”
“I’m playing such a bitch; why is she being such a killjoy? Why is this how you’re portraying women? Ninety-eight percent of the time it was an amazing experience, but it was hard for me to love the movie.”
Her comments did not go down well with her costar Seth Rogen and the film’s creator Judd Apatow, who expressed their fury in an interview with 60 Minutes.
“I hear there’s a scene [in The Ugly Truth] where she’s wearing underwear with a vibrator in it,” Rogen said. “So I’d have to see if that was uplifting for women.”
Apatow stated his disappointment and hopes that the actress would call him to apologise, but revealed that she had not yet done so.
Taylor Swift on Entertainment Tonight
While walking the red carpet at the 2015 Grammys, a reporter from Entertainment Tonight stopped Taylor Swift for a quick chat, but things quickly turned awkward when the interviewer suggested the singer would likely be going home with more than just awards.
“As I was telling you ahead of time, you’re going to walk home with maybe more than just a trophy tonight. I think lots of men,” the reporter said.
“I’m not going to walk home with any men tonight,” Swift quickly responded, with an unamused face. “I’m gonna go hang out with my friends, and then I go home to the cats. Men get me in trouble.”
Emma Thompson on Sky TV
Emma Thompson shut down an interviewer from Sky TV who repeatedly asked her questions about the Royal family, despite her expressing her disinterest in the subject.
When asked about the then-impending nuptials behind Prince Harry and Meghan Markle, Thompson replied that there’s “not a single thought about it in my head to share with you, I’m so sorry.”
When prodded again, the actress replied:
“I haven’t even… It doesn’t occur to me actually, my son’s getting married next year so I am much more sort of dealing with that, but really I have nothing to say about it.”
Then, as if she hadn’t answered the question comprehensively enough, she was then asked whether or not she wished the couple well.
“Obviously, yes, but I don’t know them,” she snapped back. “Of course I do. Stop it, just stop it, okay! Stop doing the, ‘Ooh, let’s talk about the royal wedding’. Just give the poor kids a break.'”
Ariana Grande on Power 106 FM
In 2015, Ariana Grande embarrassed two male radio hosts when they asked her a series of stupid questions, until one sexist ‘would you rather’, sent the singer over the edge.
“If you could use makeup or your phone one last time, what would you pick?” one of them asked.
“Is this men assuming that that’s what girls would have to choose between?” Grande shot back. “You need a little brushing up on equality,” she continued.
Later in the interview, she was also asked what she would like to change most in the world, to which she replied:
“I have a long list of things I’d like to change …I think, judgement in general. Intolerance, meanness, double standards, misogyny, racism, sexism. You know, all that shit. There’s lots we’ve got to get started on. That’s what we need to focus on. We have got work to do … We’ll start with you, though.”
Scarlett Johansson on Extra
While on a press tour for The Avengers in 2012, Jerry Penacoli from Extra asked Scarlett Johansson if she wore underwear beneath her Black Widow costume.
“You’re like the fifth person that’s asked me that today,” Johansson said, unimpressed.
“What is going on? Since when do people start asking each other in interviews about their underwear?” she continued.
The reporter attempted to explain the reasoning behind his question, claiming that her costume was so ‘skin-tight’ it simply begged an answer.
“I’ll leave it up to your imagination. Whatever you feel like I should be wearing or not wearing under that costume,” she finished.
