Mariah Carey, Lindsay Lohan and Taylor Swift are just a few of the celebrities that have endured awkward interviews.
It’s no secret that celebrities and media are mutually exclusive - you can’t have one without the other just like you can’t have movies without those poorly paid writers.
But what happens when the media upsets their celeb counterpart? What happens when an interview includes such an ill-phrased question that the star shuts down mid-interview, or worse yet, walks out?
Over the years, we have seen many wild moments. From Robert Downey Jr being asked about his drug-fuelled past while promoting a Marvel movie, to Paramore’s Hayley Williams being asked when the last time she orgasmed was - there’s been no shortage of ‘oh my god’ moments.
Here are seven shocking interview moments that will go down in history:
Whether you love her or find yourself entranced by her Instagram posts, it’s fair to say Britney Spears has had her fair share of hardship. One particular moment saw a heartbreaking interview with ABC powerhouse Diana Sawyer who had the star in tears.
In 2003, Sawyer sat down with the Toxic singer to discuss multiple things, one being her breakup from Justin Timberlake. It was a topic that should have been handled with care but minute 22 of the interview appears to show it was anything but.
Years later, Spears spoke out about the interview with a scathing now-deleted Instagram post, writing: “Do we dare forget the Diane Sawyer interview in my apartment almost 20 years ago?” she wrote. “What was with the ‘You’re in the wrong’ approach?? Geeze ... and making me cry???”
She continued, to address her split from Timberlake, claiming she was “in shock” following Sawyer’s questions about it. “Something I never shared when I had that breakup years ago was that I couldn’t talk afterwards,” she wrote, before adding, “I was in shock ... pretty lame of my dad and three men to show up at my door when I could hardly speak ... two days later they put Diane Sawyer in my living room ... they forced me to talk!”
Her father Jamie Spears released a statement shortly after denying involvement in the interview.
@user147589987 The Olsen twins 2004 interview with Oprah #olsentwins #oprahwinfrey #interview #fyp #2000s #tw
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In 2004, when the twins were only 17 years old, Mary-Kate had been hounded by the press about her weight. Following intense media speculation that the former Full House star was suffering from an eating disorder, Oprah Winfrey decided to take matters into her own hands and ask the star about the rumours during an appearance on her show.
Outright asking what dress size Mary-Kate and her sister Ashley were, Winfrey said, “I know there’s been a rumour that has recently surfaced that’s really upset you.”
The twins were clearly taken aback as Winfrey continued, “You know, the one about the eating.”
Mary-Kate looked almost to be on the verge of tears as she nervously tucked her hair behind her ear while Ashley jumped in to rescue her.
“We try not to read the good or the bad because it just kind of comes with the territory. Either you’re too fat or you’re too skinny …” continued Ashley before she was interrupted mid-sentence by Winfrey who problematically asked, “What size are you by the way?”
“Size ... ?” Ashley said shocked before trying to joke off the questions, “I’m short”.
A 1999 interview has revealed the moment former Spice Girl Victoria Beckham was asked by British talk show host Chris Evans to weigh herself mid-interview.
Having given birth to her and David Beckham’s eldest son, Brooklyn, just two months ago, Evans appeared to interrogate the singer-turned-fashion designer on her post-pregnancy body before forcing her to stand on a set of scales three and a half minutes into the interview.
“A lot of girls want to know because you look fantastic again,” he said. “How did you get back to your shape after birth?’ Victoria appeared cool, calm and collected as she explained her exercise regime before Evans then asked: “Is your weight back to normal?”
Victoria stated that she was back to her pre-pregnancy weight however Evans was not convinced and presented a set of scales as he said, “Can I check? Do you mind?” Visibly uncomfortable, Victoria said, “Oh no,” before adding, “This is horrible.” The star then stepped on the scales while Evans read out her exact weight to both the live audience and the nation.
She may be known for writing songs about love, heartbreak and all the dating emotions in between, but while she is open about her relationships with men in her music, when it comes to interviews it’s clear any questions are to be avoided.
While walking the Grammy Awards red carpet in 2015, the beloved songstress was asked by Entertainment Tonight host Nancy O’Dell about her plans that evening with the O’Dell joking only 25 seconds into the chat that the star will be heading home with “lots of men”.
“You’re going to walk away with more than a trophy tonight, I think, lots of men,” the reporter said which was quickly met by a very telling icy stare from the then 25-year-old Cruel Summer singer.
“I’m not going to walk home with any men tonight,” Swift firmly stated before doubling down on her answer adding, “I’m going to hang out with my friends, and then I go home to the cats.”
@adam_birmingham anyone else feel uncomfortable? 🤣😅😂 #johnahill #hollywood #fatguy #fatguyinhollywood #comedy #funny #hilarious #interview #celebrities #fyp #viral
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Jonah Hill showed fans why it’s important to live by the motto “If you’ve got nothing nice to say, say nothing at all” after a reporter made an insensitive comment about his healthier lifestyle.
Despite the Superbad actor sharing snippets of the reason for his weight loss journey in recent years, he has mostly kept quiet about his transformation, even sharing an Instagram post asking people to stop asking him about it completely, however, one journalist decided to try his luck during a 2011 interview.
While doing the media rounds for his then-newly released film, Moneyball, the actor was asked about his inspiration for the life-changing decision admitting, “I just decided one day I wanted to be healthier, and I went and saw a nutritionist.”
As a follow-up question, another reporter asked Hill whether he was ‘still considered the fat guy’ in certain situations, like at parties and it clearly upset the actor.
Trying to justify their question, the reporter said: “I run into that a whole lot. I’m the fat one. So are you the fat guy in Hollywood still or does everyone like look at you and they’re like ‘oh this is great, now you’re healthy’?”
Pondering the question before choosing to ignore it, Hill said “Do you have any other questions? That are smart?” before moving on to another reporter’s question.
Howard Stern has become a household name with his long-running radio show The Howard Stern Show, but his career hasn’t come without controversy.
In 1998, while interviewing the beloved singer Mariah Carey on his show, he made multiple inappropriate comments that caused discomfort for both the singer and the audience. It all started when Carey asked what kind of shots the camera would be getting, with Stern responding, “Right up your dress!” Prepared for the comment, the superstar hit back saying, “I’m not sure about what’s going on, and you guys can be a little bit lewd sometimes.”
Despite calling out the host, Stern did not take the hint and added, “Why didn’t you flash me on stage?” He then drew attention to her breasts multiple times. Ignoring the shocking comment, Carey brought up prior mean things Stern made on his show and warned him not to do the same with her, however he completely ignored her and continued to ask inappropriate questions such as, “Do you ever wear underwear, ever?” and “Are you wearing underwear tonight?”
Carey eventually said, “Howard, don’t say that. You’re making a mockery of me,” before suggesting the interview would be cut short.
It’s no secret Lindsay Lohan has suffered from substance abuse issues, but it’s clear she prefers to avoid interviews about her experience. Despite this, David Letterman sat down with the star in 2013 and subjected her to an insensitive line of questioning.
Then 26 years old, the actress appeared on The Late Show to talk show to promote her new horror comedy Scary Movie 5, but instead was brought to tears by Letterman’s off-script questions.
Sitting down with Lohan, the host said, “Aren’t you supposed to be in rehab now?” Adding, “How many times have you been in rehab?”
Lohan, who could be seen repeatedly looking to someone standing off-camera, replied: “Several.”
Letterman then asked, “How will this time be different? What are they rehabbing, first of all? What is on their list? What are they gonna work on when you walk through the door?” The audience began laughing however it was no laughing matter with Lohan saying that those particular questions were not mentioned in the segment’s “pre-interview”.
“Do you have addiction problems?” Letterman continued to probe. “Is it alcohol? Do you drink too much?” Later in the interview, Letterman revealed a printed-out list of things Lohan “has endured”, which Lohan grabbed from him and asked him not to read out loud. “You can’t make a joke of it,” Lohan said upset. “That’s so mean.”
Lillie Rohan is an Auckland-based reporter covering lifestyle and entertainment stories who joined the Herald in 2020. She specialises in all things relationships and dating, great Taylor Swift ticket wars and TV shows you simply cannot miss out on.
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