Top 10 Disturbing Celeb Interviews With What We Know Now
#10: David Letterman
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The 2021 documentary “Framing Britney Spears” sparked online discussions about the media’s treatment of female celebrities. Amid that backdrop, former “Late Show” host David Letterman came under fire for some of his past interviews. Arguably the most disturbing occurred in 1998, when he interviewed actress Jennifer Aniston, who was promoting her film “Object of My Desire”. During their conversation, Letterman suddenly approached a visibly uncomfortable Aniston and sucked on a strand of her hair. He then handed her a tissue to wipe the saliva off. The veteran host was also taken to task for a 2013 interview with Lindsay Lohan, where he ambushed her with several inappropriate questions, leading her to tear up at one point.
#9: Jussie Smollett
On January 29th 2019, “Empire” actor Jussie Smollett reported that he had been the victim of an alleged hate crime in Chicago. Smollett claimed that two men had attacked him in the early hours of the morning, while yelling racial and homophobic slurs at him. When authorities launched an investigation into the alleged attack, several inconsistencies in Smollett’s story began to emerge. On February 14th, the actor discussed the incident in an interview with ABC’s Robin Roberts, expressing that he was “pissed off” at those who doubted his story. However, less than a week later, it was revealed that Smollett had indeed staged the attack, leading to his criminal indictment for filing a false police report.
#8: Mary-Kate & Ashley Olsen
Back in 2004, celebrity twins Mary-Kate and Ashley Olsen were still teenagers when they appeared on “The Oprah Winfrey Show”. During the interview, Winfrey brought up reports that Mary-Kate had been dealing with an eating disorder. Ashley immediately came to her defense, stating that they didn’t care about what was discussed in the tabloids. However, Winfrey interrupted Ashley with an inappropriate question about their weight, leaving both sisters visibly surprised. This was particularly disturbing given the fact that the twins were minors at the time, and Mary-Kate would seek treatment later that year for an eating disorder. When the interview resurfaced in 2021, Winfrey faced intense criticism for her handling of the situation.
#7: Ashton Kutcher
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In 2023, Hollywood couple Ashton Kutcher and Mila Kunis came under fire after writing letters of support for their former co-star Danny Masterson, who was convicted of sexual assault. Subsequently, one of Masterson’s accusers shared a clip from a 2003 episode of Kutcher’s show “Punk’d” where he made a seemingly predatory comment about actress Hilary Duff. This remark made by Kutcher, who was 25 at the time, raised significant concerns about his behavior. The backlash on the actor further intensified after another clip from a 2002 interview on “The Rosie O’Donnell Show” resurfaced. In it, Kutcher gleefully admitted to participating in a bet with Masterson to french-kiss Kunis on-screen without her consent, even though she was still a minor.
#6: Ellen DeGeneres
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Talk show hosts have always found creative ways to get the scoop on the lives of their celebrity guests. But Ellen DeGeneres seemed to have crossed a line in a 2008 interview with Mariah Carey that left the singer “extremely uncomfortable”. In a bid to confirm pregnancy rumors, DeGeneres offered Carey champagne and pressured her to drink it. Carey, who looked a bit uneasy, initially tried to fend her off but eventually appeared to take a small sip. DeGeneres interpreted this as confirmation and proceeded to celebrate. However, in 2020, Carey disclosed that she wasn’t ready to share the news at the time due to a previous miscarriage. Tragically, she lost the pregnancy shortly after the controversial interview.
#5: Matt Lauer
The MeToo movement led to the downfall of several industry heavyweights, including longtime “Today” host Matt Lauer. Lauer was fired by NBC in November 2017 after allegations of “inappropriate sexual behavior in the workplace” came to light. Following his dismissal, a peculiar 2009 interview with actress Sandra Bullock resurfaced. Bullock was there to promote her film “The Proposal,” only to be bombarded with remarks about her nude scenes. Lauer displayed an unsettling excitement at the thought of seeing the actress naked, even adding that the image had become his screensaver. Many found this disturbing, especially in light of his sexual misconduct allegations. At the end of the interview, Lauer asks Bullock to return soon, an invitation she instantly declines.
#4: Ben Affleck
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In the wake of the MeToo movement, many began to re-examine past behavior of celebrities that was once normalized. Enter actor and filmmaker Ben Affleck. In October of that year, actress Hilarie Burton alleged that Affleck had groped her during a 2003 appearance on MTV’s “Total Request Live”. Following this allegation, the actor issued a statement apologizing for his inappropriate behavior. Shortly after, another video resurfaced from a 2004 interview with Canadian journalist Anne-Marie Losique. In it, Affleck tightly embraces Losique and makes suggestive comments about her body. At first glance, it appears highly inappropriate and raises questions about Affleck’s behavior towards women. According to Losique, however, it was all an intentional act for the cameras, to boost ratings.
#3: Britney Spears
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In 2003, shortly after her high-profile split from Justin Timberlake, Britney Spears sat down with veteran TV presenter Diane Sawyer. During the interview, Sawyer asked Spears a slew of questions that would be uncomfortable for anyone to answer, let alone a 21-year-old. Among other topics, she grilled her about the break-up with Timberlake and also seemingly defended a statement by then-First Lady of Maryland, who said she would shoot Spears if given the opportunity. Needless to say, the now infamous interview felt more like an interrogation. At one point, the singer even broke down in tears. The clip ignited a wave of criticism directed at Sawyer, after it was featured heavily in the 2021 documentary “Framing Britney Spears”.
#2: Danny Masterson
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Who knew late night talk show hosts could predict the future? As earlier mentioned, Hollywood actor Danny Masterson made headlines in 2023 after he was convicted of sexually assaulting two women in the early 2000s. He received a prison sentence of 30 years to life for these crimes. Masterson’s sentencing led to the discovery of an old clip from his 2004 appearance on “Late Night With Conan O’Brien”. When asked about his lack of a Long Island accent, the actor’s response was an uncomfortable joke with a vulgar undertone. Perhaps sarcastically, O’Brien quipped that Masterson’s day of reckoning would soon come. It may have taken nearly two decades, but that statement ultimately came to fruition.
#1: Bill Cosby
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Disgraced actor and comedian Bill Cosby has faced dozens of sexual assault allegations throughout his career. Many of his accusers claim that Cosby drugged them before committing the despicable acts. These allegations may not come as a surprise considering that in a 1991 interview on CNN’s “Larry King Live,” Cosby seemingly alluded to spiking people’s drinks. Speaking with King, the comedian made a joke about Spanish Fly, a drug used as an aphrodisiac. Cosby talked about dropping the pill in a lady’s drink as a means of having one’s way with her. Even King joins in on the topic, concluding Cosby’s lewd joke with “She’s yours!” We’d say it’s a disturbing clip, but even that seems like an understatement. What other celeb interview do you think needs a reassessment? Sound off in the comments.
