Some celebrities can be a bit eccentric in interviews, but these celeb interviews are straight-up disturbing. Here are the most memorable on-screen interviews that are upsetting to watch because of the controversies that surround the people involved. From Bill Cosby to Britney Spears, here are some interviews that will haunt you because of the actions of either the interviewers or the interviewees.
10. David Letterman
The media’s treatment of Britney Spears has been the subject of numerous discussions, during which David Letterman faced criticism for his previous interview misconduct. When he interviewed Jennifer Aniston in 1998, he sucked on a strand of her hair, which looked uncomfortable, and gave her a tissue to wipe herself off. He also borderline harassed Lindsay Lohan in a 2013 interview, asking her so many inappropriate things she cried.
9. Jussie Smollett
The world felt sympathy for Smollett when he reported himself as the victim of a hate crime. However, as the investigation progressed, it unearthed inconsistent details that raised questions. Although Smollett was interviewed by Robin Roberts of ABC and said he was “pissed off” by anyone who thought he was being dishonest, just days later, it was revealed that Smollett was, in fact, lying and had staged the event.
8. Mary-Kate & Ashley Olsen
During their 2004 interview on “The Oprah Winfrey Show,” Winfrey ambushed Mary-Kate with accusations of having an eating disorder. Ashley came to her sister’s defense, but Winfrey unprofessionally interrupted, asking about their weight. This is especially inappropriate, seeing as the girls were minors. Later that year, Mary Kate got treatment for anorexia. Years later, Oprah Winfrey faced criticism for her handling of this situation.
7. Ashton Kutcher
Ashton Kutcher and his wife, Mila Kunis, both faced intense scrutiny after supporting friend and ex-co-star Danny Masterson, who had been convicted of sexual assault. Shortly after, one of Masterson’s victims shared a clip from Punkd, in which a 25-year-old Kutcher made a predatory comment about a young Hilary Duff. It got worse when the internet exposed a “The Rosie O’Donnell Show” interview with the actor, who cheerfully said he French-kissed Kunis on the set of “That 70s Show” without getting her consent. She was a minor at the time.
6. Ellen DeGeneres
When DeGeneres interviewed Mariah Carey in 2008, her lack of professionalism and bullying attitude didn’t paint her in the best light. Attempting to confirm rumors of a pregnancy, DeGeneres offered Carey a glass of champagne and tried to coerce her to drink it. To avoid rumors, she took a small sip, but as the singer revealed in 2020, she remained silent due to a previous miscarriage and didn’t feel comfortable sharing the information. Sadly, she lost the baby not long after the interview.
5. Matt Lauer
Matt Lauer was fired by NBC in 2017 after the MeToo movement led to several high-profile men reaching their demise. Following his dismissal for inappropriate sexual misconduct at work, a 2009 interview between Sandra Bullock and Lauer surfaced. Lauer was disturbingly excited to bring up Bullock’s nude scenes and even said that an image of her without clothes was his screensaver. As the interview ended, he asked her to return to the show soon, which the actress quickly declined.
4. Ben Affleck
After #MeToo, actress Hilarie Burton accused actor Ben Affleck of groping her when she was on a 2003 episode of “Total Request Live” on TLC. Although Affleck apologized for acting inappropriately, another video came out of a 2004 interview conducted by a Canadian reporter named Anne-Marie Losique. In the footage, he tightly gripes her body and makes suggestive comments about it.
3. Danny Masterson
As we discussed previously, actor Danny Masterson was convicted of sexually assaulting multiple women. His sentence was 30 years to life, and during the period where he was sentenced, a 2004 interview on “Late Night With Conan O’Brien” showed Masterson responding to a joke about his accent with a vulgar and inappropriate joke. O’Brien joked back that he would be “caught soon,” but little did either man know that the statement would predict the future.
2. Britney Spears
After breaking up with Justin Timberlake in 2003, Britney Spears was interviewed by Diane Sawyer, who asked the starlet a stream of uncomfortable questions. She pressured the 21-year-old to answer questions about the breakup and appeared to defend Kendel Ehrlick, the former First Spouse of Maryland, who said she would shoot Spears if she had the chance. The entire interview came off as an abusive interrogation, one during which Spears started to cry.
1. Bill Cosby
Bill Cosby’s court case lives on in infamy these days. The celebrity dealt with dozens of allegations of sexual assault throughout the years when it came to light that he drugged his victims before assaulting them. It’s not too surprising when you look at a 1991 interview with Larry King, where Cosby casually referenced spiking women’s drinks. He jokes to the talk show host about Spanish Fly, a supposed aphrodisiac, which he would drop into a woman’s drink so that he could do whatever he wanted with her.