Top 28 Most Disturbing Celeb Interviews Because of What We Know Now

Once considered one of Hollywood’s most promising up-and-coming actors, Majors was found guilty of assault and harassment in December 2023. Originally set up to portray Kang the Conqueror, the Marvel Cinematic Universe’s new super-baddie, the actor was barred from any future MCU participation in light of his conviction. As such, this February 2023 Stephen Colbert interview, released just weeks before his initial arrest, now plays out as though it’s from an alternate universe. When prompted by Colbert to explain his well-documented trait of carrying around his own mug, it’s chilling to watch Majors comment on his then-rising star profile, knowing that it would shortly be ripped away.

This May 23, 2005 interview has since become the stuff of pop culture legend. Much has been made of the Oscar nominee’s wildly animated appearance on “The Oprah Winfrey Show.” However, it’s hard to deny its cringiness, even to this day. Cruise had only begun dating Katie Holmes about a month before the infamous “Oprah” appearance, which makes his behavior on the show even more confounding. It’s tempting to chalk Cruise’s outbursts up to being in the “honeymoon phase,” which clearly did not last. Cruise’s “Oprah” interview takes on an uncomfortable new light once you consider the alleged details of his and Holmes’ ugly divorce.

Who knew that this seemingly innocuous interview would haunt “Tonight Show” host Jimmy Fallon, personally and professionally, for years after? Although it may seem hard to believe now, in the aftermath of his two presidencies, President Trump’s candidacy was hardly taken seriously — at least initially. A Sept. 15, 2016 appearance on “The Tonight Show” found Fallon in hot water for supposedly humanizing then-candidate Trump by asking to tousle his infamous head of hair. Trump, who even then had been harshly criticized for offensive remarks about women, minorities, and more, later denounced Fallon’s backtracking. Watching the Trump-Fallon interview now serves as a stark reminder that the president should’ve been taken seriously even then.

Woof. Broadway Joe, what happened here? The widely-revered NFL and Super Bowl champion has long been considered one of the greatest football players of all time, but his antics off of the field have warranted nearly as much attention as his actual playing. Namath has been open about his struggles with substance use disorder — alcohol, in particular. His personal difficulties reached a nadir on December 20, 2003, when a sideline interview with reporter Suzy Kolber culminated in Namath repeatedly telling the journalist that he wanted to kiss her. While Namath quickly apologized, watching this clip in the post-#MeToo era is a tall order.

This interview barely even had a chance to get started before both “Tonight Show” host Jay Leno and his other guest, celebrity chef Gordon Ramsey, took it to an uncomfortable place. You can’t help but feel bad for Emmy nominee Vergara, who’s immediately the subject of… let’s say… unwanted attention. Both men crack several lewd, off-color jokes about the “Modern Family” star, making inappropriate comments about her body and physical appearance. To her credit, Vergara handles it like a professional, and never once appears poised to break. While Leno and Ramsey’s remarks were written off as jokes at the time, it’s clear that they’ve since aged like milk.

If you’re at all familiar with these legendary L.A. funk-rock provocateurs, you may not be terribly surprised to hear that they’re not exactly known for their good behavior. Although they’ve earned their reputation as hardcore partiers, it’s hard to argue that they went several steps too far during their appearance on this beloved British chat show. Following a bizarre a cappella performance, the members of the band began to antagonize host Whale’s other guest for that evening, comedian Cleo Rocos. Whale cuts the segment when singer Anthony Kiedis appears to kiss Rocos’ body without consent. The accusations of assault and misconduct against the band that have cropped up in the years since make this appearance even harder to stomach.

Where do we even start with this one? Disgraced R&B singer Kelly, as you probably already know by now, was convicted in 2019 on federal racketeering and trafficking charges involving minors. A few months ahead of his conviction and sentencing, the quote-unquote “Pied Piper” himself appeared on “CBS This Morning” for an interview with host Gayle King, in an effort to set the record straight. It goes without saying that the interview was an unmitigated trainwreck: Kelly became visibly aggravated, and did little to help his case. Given the sheer volume and credibility of the allegations against Kelly that have continued since then, it’s difficult to watch Kelly describe all of his accusers as liars.

Much like R. Kelly, Sean Combs’ alleged misconduct was a massively focused-upon news story over the course of 2024. The rapper and mogul, who’s gone by the stage names “Puff Daddy” and “P. Diddy” was federally charged with trafficking and racketeering in September 2024. Combs was dealt yet another fatal blow on October 1st of that year, when the Washington Post reported that he would face as many as 120 further lawsuits. Knowing that makes his 2002 “Late Night with Conan O’Brien” appearance an endurance test — particularly the moment when Combs tells O’Brien about the importance of locking your doors during a party.

You might not be familiar with his name, but you definitely recognize his voice. Justin Roiland rose to prominence as the co-creator and voice behind the main characters of the hit animated sitcom “Rick and Morty.” In 2023, however, Roiland was fired from the show following accusations of sexual misconduct and predatory behavior towards minors. As the scandal unfolded, a 2011 episode of his podcast “The Grandma’s Virginity Podcast” resurfaced, in which Roiland made troubling remarks about being attracted to minors. Many perceived these comments as confirmation of the allegations against him. While he was initially cleared of criminal charges, Roiland faced a barrage of new sexual assault allegations later that year, all of which he vehemently denied.

In 2020, comedian and actor Chris D’Elia was accused of sexual harassment and predatory behavior. It was alleged that he had solicited explicit pictures from his accusers, sometimes via Snapchat. After the allegations became public, an old clip from D’Elia’s appearance on the podcast “The Fighter and the Kid” resurfaced. In it, the discussion centered around a high school teacher who was caught sending inappropriate photos of herself to her student on Snapchat. This initially puzzles D’Elia, as he was of the impression that such images disappeared. But his confusion quickly morphs into astonishment when he learns that content on Snapchat can actually be saved. For some, it appeared that the comedian realized the potential consequences for his own alleged actions.

In 2017, Hollywood was rocked by numerous sexual assault allegations against movie producer Harvey Weinstein. While these claims stunned the world, they seemed to already be common knowledge within the entertainment industry. This was evident in a 2005 red carpet interview with Courtney Love at the “Comedy Central Roast of Pamela Anderson.” When asked what advice she had for aspiring actresses in Hollywood, Love warned them to steer clear of Harvey Weinstein. Following the resurgence of this video, Love disclosed on Twitter that she was essentially blacklisted by the talent firm, Creative Artists Agency, for speaking out against Weinstein. It may have taken years, but her warnings were eventually vindicated.

“Supergirl” star Melissa Benoist appeared on “The Tonight Show Starring Jimmy Fallon” in 2016, where she shared a story about a home accident. She recounted how she tripped down a flight of stairs and injured her eye by crashing into a potted plant. Despite the lighthearted delivery, it later emerged that the entire incident was fabricated. In 2019, Benoist bravely disclosed her experience as a survivor of domestic violence by an unnamed former partner. She then described a particular incident that was remarkably similar to the staircase mishap, admitting that she had made up the story to evade suspicion. Revisiting the interview, it’s distressing to think of the pain she was concealing behind her smile.

Former child actor Corey Feldman has consistently claimed that he and his fellow star Corey Haim experienced harassment from top Hollywood figures early in their careers. In 2013, Feldman revisited the issue during an interview on “The View,” where he cautioned parents about the potential dangers of putting their kids in show business. Co-host Barbara Walters promptly rebuked Feldman for his comments, accusing him of harming the reputation of the industry. Although the interview soon faded from public consciousness, it re-emerged in 2017 amid the MeToo movement, which shed light on widespread sexual misconduct in Hollywood. Walters was heavily criticized for what appeared to be her disregard for the risks faced by child actors in the industry.

In December 2023, action star Vin Diesel was sued by his former assistant, Asta Jonasson, who accused him of sexual battery and retaliation. Jonasson alleged that Diesel sexually assaulted her while filming “Fast Five” and then fired her, claiming she was “no longer useful.” These accusations brought renewed attention to a little-known interview the actor had done in 2016. Diesel was promoting his film “XXX: Return of Xander Cage” and spoke with Brazilian YouTuber Carol Moreira. During the interview, he quickly became enamored with Moreira, hitting on her relentlessly and preventing her from doing her job. Moreira later admitted that she was “completely uncomfortable” with the actor’s advances, which is pretty obvious just from watching the clip.

The comedian Louis C.K. was one of several industry heavyweights who were accused of sexual misconduct in late 2017. Five women came forward claiming that he had exposed himself to them. C.K. later admitted to the allegations and issued an apology, stating that he had “wielded [his] power irresponsibly.” This revelation prompted scrutiny of C.K.’s previous stand-up material and interviews, some of which shared troubling connections to the real-life allegations. In particular, it cast a disturbing light on a 2012 interview the comedian granted to Vanity Fair. When asked about what trait he most deplores about himself, C.K. responded with an unsettling reference to his genitals.

In 1990, Geena Davis and Bill Murray co-starred in the crime comedy film “Quick Change,” which Murray also co-directed. The film drew attention in 2022 when Davis accused Murray of sexually assaulting her during her audition. Those claims were seemingly confirmed by the actor, not in 2022, but back when the two appeared on “The Arsenio Hall Show” to promote the film. Throughout the interview, Murray repeatedly strokes Davis’ arms and at one point, even pulls down the strap of her dress, much to Davis’ discomfort. The actress recounted the claims during the interview, albeit in a more humorous manner. But in light of her 2022 allegations, there’s no way to look at the clip without feeling creeped out.

While still alive, Jimmy Savile was a widely beloved English media personality, having hosted the BBC’s “Top of the Pops” show for years. However, it wasn’t until after his death that his true nature came to light. An ITV documentary revealed that Savile was a serial sexual predator, with victims potentially numbering in the hundreds. Savile was able to disguise behind his playful character but he seemingly dropped clues about his reprehensible actions. In this 1999 appearance on the BBC show “Have I Got News For You,” Savile alluded to his predatory behavior by phrasing it as a joke. Although some of the allegations against him emerged while he was still alive, Savile managed to deflect them using similar tactics.

To be fair, this interview was disturbing even back when it was made. In 2008, R. Kelly sat down with BET reporter Touré. Earlier that year, the singer had been acquitted in a trial centered around his possession of highly inappropriate material. Touré bluntly asked Kelly if he was attracted to minors. Instead of a flat-out negative response, Kelly asked for further clarification, which was just as bad as answering in the affirmative. Even with such an inappropriate response, the interview had no significant consequences on his career. It would take a little over a decade, with the release of the 2019 docuseries “Surviving R. Kelly,” for this interview to take on an even more troubling layer.

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 “The Object of My Affection”. 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.

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.

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.

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.

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.

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.

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.

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”.

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.

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.


Which interview was the hardest for you to watch? Are there any we missed? Let us know in the comments!