10 Disturbing Interviews With Celebrities
James Brown
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1988 In the music world, Brown was a legend. But his personal life was shadowed by scandal. In 1988, he was arrested for domestic assault. Brown was then interviewed on CNN by Sonya Friedman, and it didn’t go well. Brown behaved erratically throughout. He randomly sang to avoid answering any intense questions. Yet when he did decide to answer something, it wasn’t very coherent. Except when it came to his gospel magazine, then Brown responded articulately. It was bizarre. At the end, he sang, “this is a man’s world,” only for Friedman to sarcastically thank him for reminding everyone. In the aftermath, people were convinced Brown was under the influence, something he had a troubled history with.
Britney Spears
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2003 In 2003, ABC interviewed Britney Spears, who was going through a public breakup with Justin Timberlake at the time. Diane Sawyer was given the task of getting the big scoop. But instead of achieving that, the journalist thought it was a good idea to verbally berate the pop star. Sawyer told Spears that then-First Lady of Maryland Kendel Ehrlich had proclaimed she would shoot Spears if the opportunity arose. Sawyer then seemingly emphasized with Ehrlich as she criticized Spears’s influence on children. Yikes. Add in sections of Sawyer asking the “Toxic” singer about her virginity and accusing her of cheating on Timberlake, and we have an incredibly long and uncomfortable chat. In 2021, Spears posted on social media slamming this infamous interview.
Lindsay Lohan
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2013 In 2013, Lohan appeared as a guest on the “Late Show with David Letterman” to promote “Scary Movie 5.” Instead, she was ambushed with a series of questions about her stint in rehab and her addiction issues. As she points out, this wasn’t an agreed topic. Lohan then sees a list of her scandals Letterman had written down and the jokes attached. At one point, Lohan seems to cry from Letterman’s constant questioning. But this isn’t the only time the talk show host has been bizarre with his methods. In 1998, with Jennifer Aniston as a guest, Letterman creepily got close to her, put her hair in his mouth, and sucked on it. Yep, that happened for some reason.
Kanye West
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2018 In recent years, Kanye West, now known simply as Ye, has seen many controversies. But perhaps the most infamous was when he arrived at the TMZ office for a chat in 2018. Kicking things off, he begins with rambling responses before delving into his passion for Donald Trump. And then, West seems to suggest that because slavery went on for 400 years, it was a choice for the victims. Yikes. He then goes further by suggesting the black community is “mentally imprisoned.” This sparked a member of the TMZ staff to fire back with their disgust at West’s comments. Afterward, the rapper attempted to walk back his comments on social media by stating he knows that people weren’t shackled out of free will.
Charlie Sheen
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2011 In 2011, the “Two and a Half Men” actor watched his professional and personal life collapse due to addiction problems. After the show went on hiatus, instead of keeping his head down, Sheen took part in a series of unsettling interviews. One of the big ones was with ABC. There, the actor spoke about his addiction problems and dropped in the infamous “tiger blood” message. Next, he claimed he was on a substance called “Charlie Sheen” and told the interviewer that if they tried it, they would perish and their face would melt off, a disturbing visual, indeed. A few days after the interview, Sheen’s contract on the sitcom was torn up.
Megan Fox
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2009 In 2020, an interview with Fox on “Jimmy Kimmel Live!” in 2009 was rediscovered and went viral for all the wrong reasons. The actor talked about the time she was an extra for a club scene for Michael Bay’s 2003 film, “Bad Boys II.” Because she was only fifteen then, she couldn’t hold a drink or sit at the bar during filming. So, Bay had her in a bikini, dancing under a waterfall instead. Ew. Fox then made the point that that’s how the director’s mind works. Kimmel, instead of being disturbed, joked that that’s how everyone’s minds work, apparently. Fox is clearly uncomfortable at her grim story being used for an inappropriate punchline before the topic quickly moves on.
Sean Connery
1987 James Bond is already not the most progressive action hero, especially the portrayal of him from the Connery era. And this interview with the actor reflects some of those aspects. In 1987, Connery spoke to ABC’s Barbara Walters. Having already made problematic statements about women in the past, he reaffirmed his beliefs when Walters brought them up. Connery claimed that if every other method has been exhausted, then it’s okay for a man to strike a woman. He spoke about women with such venom throughout, talking as though they’re some kind of subspecies. It’s frankly gross. Walters did a great job at keeping her cool and basically letting Connery tarnish his own reputation.
Prince Andrew
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2019 With serious allegations about Andrew and his relationship with Jeffrey Epstein swirling, the UK Royal took to BBC’s “Newsnight” for an in-depth interview to address the scandal. And it didn’t work. The interview conducted by Emily Maitlis, Andrew didn’t apologize to Epstein’s victims and didn’t regret his friendship with the convicted offender. When talking about his own scandal for possible underage relations, his excuse was bizarre. The allegations stated that, in 2001, Andrew was sweaty after dancing at a London club with then-seventeen-year-old Virginia Giuffre. He claimed that as a result of an “adrenaline overdose” during the Falklands War, he couldn’t sweat at the time. The interview did the opposite of what Andrew wanted and strengthened the rumors about his possible misdeeds.
O. J. Simpson
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2006 In 1995, the former NFL star was found not guilty of the slaying of his ex-wife Nicole Brown Simpson and her friend Ron Goldman. Many watching the unfolding court case were stunned at the verdict. In 2018, Fox released an interview they did with Simpson back in 2006. The corporation was banned from airing it at the time. Speaking with Judith Regan, Simpson conducts a hypothetical exercise. Pretending he was at the scene, he explores what happened on that fateful night to Brown and Goldman. Throughout, Simpson nervously chuckles as he goes into vivid detail about how he hypothetically slayed the two alongside his friend “Charlie.” This interview brought up uncomfortable memories for many, as well as made Simpson look incredibly suspicious.
R. Kelly
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2019 In 2019, with the allegations against the R&B singer gaining a lot of traction, Kelly tried to clear his name in an interview for CBS with Gayle King. And it backfired spectacularly. With erratic behavior, Kelly was questioned on the allegations stemming from the documentary “Surviving R. Kelly.” He claimed everyone was lying about him before attempting to cry. When that didn’t go to plan, and King further challenged him, Kelly went with an anger-filled rant. He seemingly attempted to make it look like he was the victim in this situation. Throughout Kelly’s unhinged and disturbing behavior, King was completely unfazed, which, relatively speaking, was incredibly impressive.