Cringe-Worthy Moments In Diane Sawyer Interviews

Diane Sawyer is regarded as one of the most prominent TV journalists of our time. After decades of working with ABC News, including on Good Morning America, Primetime, and 60 Minutes, the anchor is known for her hard-hitting questions, and like any good interviewer, Sawyer obviously knows how to get down to the bottom of topics that her subjects might otherwise avoid. Naturally, this has led to some pretty cringe-worthy moments, some of which have made headlines years later.

In the wake of The New York Times’ Framing Britney Spears documentary, people are beginning to analyze the way we treat celebrities in Hollywood, and Sawyer’s interviews have begun to spark controversy — and not just the one she did with Spears, either. Looking back, several of her sit-downs have included moments that probably never should have happened on camera, and it’s pretty awkward to see the celebrities she’s talking to become so visibly uncomfortable.

We definitely have to give these celebrities props for hanging in there, particularly because these interviews are now preserved in internet infamy and only get more awkward with time. So without further ado, here are the most cringeworthy moments of Sawyer’s career. 

Diane Sawyer blamed Britney Spears for her breakup with Justin Timberlake

In a November 2003 ABC Primetime interview, Diane Sawyer asks a then 22-year-old Britney Spears about her split from Justin Timberlake, seemingly blaming her for whatever had gone wrong between them. Up until this point, Spears had mostly remained quiet on the breakup, while Timberlake had frequently addressed it in interviews, as well as released his hit 2002 single, “Cry Me A River,” about the end of their relationship. 

“He has gone on television, and pretty much said you broke his heart. You did something that caused him so much pain, so much suffering. What did you do?” Sawyer asks Spears. After Spears says that they were “both really young” and a breakup was inevitable, Sawyer pushes even further, bringing how Spears said Timberlake was the only person she’d ever slept with, and asking her why the former NSYNC star would have said she cheated if that were true.

“I think everyone has a side to their side of the story, and to make them feel a certain way … and I’m not technically saying he’s wrong, but I’m not technically saying he’s right, either,” Spears responds, even adding, “This feels really awkward right now.”

The segment later sparked headlines, including at Buzzfeed in February 2021, which claimed that viewers had once again become “enraged” by the resurfaced line of questioning that they viewed as clear examples of “slut-shaming” and misogyny.

The inappropriate way Diane Sawyer framed this question about being a role model

Another cringeworthy moment in Britney Spears’ 2003 interview with Diane Sawyer comes when Sawyer brings up how “Spears has upset a lot of mothers in America” with the way she dresses and her on-stage performances — and she takes it a step further when she plays an audio clip for Spears from Kendel Erlich, the former governor of Maryland’s wife, who says, “Really, if I had the opportunity to shoot Britney Spears, I would.”

Spears is understandably horrified in the moment and calls the statement “really sad” as she looks completely taken aback by it. “I’m not here to babysit her kids,” she says, later adding that the only person she feels responsible for setting a good example for is her younger sister, Jamie Lynn Spears.

Reflecting on the interview now, everyone from fans to talk show hosts are aghast as Sawyer’s questions, especially after clips from it were used by The New York Times documentary Framing Britney Spears as examples of how wrongfully Spears has been treated in the media. On a February 2021 episode of The Talk, co-host Amanda Kloots even said, “Diane Sawyer does owe [Spears] an apology” — and that certainly seems to be a common theme among Spears’ fans, who have been extremely vocal about the interview on social media. So far, Sawyer has not responded to any of this, and Spears has yet to comment on the interview with Sawyer itself.

Diane Sawyer asked Whitney Houston if she abused drugs

During Diane Sawyer’s 2002 interview with Whitney Houston, she shows the singer photos of herself, insisting that she is “scary thin.” Houston becomes visibly annoyed at the interrogation and even hands Sawyer the photos back, but that doesn’t stop Sawyer from pressing her on rumors that she has an eating disorder or uses drugs, which leads to Houston dropping a line in response that ended up living on long after the legendary singer died. “First of all, let’s get one thing straight,” Houston says. “Crack is cheap. I make too much money to ever smoke crack. Let’s get that straight, okay? We don’t do crack. … Crack is whack.”

After Houston’s death ten years later, the coroner’s report revealed that her cause of death was “drowning and effects of atherosclerotic heart disease and cocaine use,” according to The Washington Post. And in a 2013 interview with Harper’s Bazaar, Sawyer revealed she counted that moment among the ones she had been most affected by. “I think when Whitney Houston was doing that somewhat famous interview, she was learning — she was saying it for the first time,” Sawyer told the outlet.

Again, fans have revisited the interview and shared their outrage on social media. In just one example, writer Jamal Jordan tweeted, “I spent my afternoon watching clips from Diane Sawyer’s older interviews with Britney Spears, Michael Jackson and Whitney Houston and I feel like ABC News straight up owes the American public an apology.”

Critics think Diane Sawyer crossed an emotional boundary with Jennifer Aniston

In January 2004 — just a year before Jennifer Aniston and Brad Pitt went their separate ways — Diane Sawyer interviewed the Friends star and asked her questions in a way that YouTube commenters described as “exploitative” and “a session of therapy, a very cruel one.” The interview becomes particularly uncomfortable when Sawyer brings up Aniston’s strained relationship with her mother, Nancy Dow, showing Aniston photos from her childhood that were printed in the book that Dow had written (and that Aniston had intentionally chosen not to read). Many of them were pictures Aniston had never seen, or was seeing for the first time on camera, making this an incredibly personal moment that was caught on camera.

It’s enough to bring Aniston to tears, but Sawyer keeps asking her why she hasn’t forgiven her mother, and what it would take for her to move past their disagreement and repair their relationship, even after Aniston admits in the interview that her mother had made many comments about her appearance growing up.

Despite how fans might feel, however, Aniston certainly doesn’t harbor any ill feelings towards Sawyer. In fact, while discussing with Jimmy Kimmel in 2019 how she prepared to play a news anchor on the Apple TV+ series The Morning Show, Aniston said she “had dinner” with Sawyer. “I love, I worship [Diane Sawyer],” Aniston even said, adding, “If I could emulate anyone it’s her.”

Diane Sawyer pressed Rihanna to talk about the abuse she suffered by Chris Brown

After the world found out about the abuse Rihanna suffered at the hands of Chris Brown when TMZ published a police report and photos of her injuries from that night in 2009, the singer agreed to sit down with Diane Sawyer and talk about the situation on 20/20. Although the entire purpose of the interview was for Rihanna to be able to tell her side of the story once and for all without holding back, some fans believed that Sawyer took her questioning to a place that quickly became exploitative in light of everything Rihanna had been through in the abusive relationship. 

At one point in the interview, Sawyer shows Rihanna the photos of her bruised face before playing her comments from people saying she must have done something to provoke Brown to hit her. And even when Rihanna states that she is “embarrassed” and “humiliated” to see the photos, Sawyer pushes on.

Fans on YouTube have accused Sawyer of victim-shaming and intentionally “going for tears,” comparing this interview to the one she did with Britney Spears — and some people on Twitter certainly seem to agree. As for Rihanna herself, though? Looking back, she saw it as an opportunity to put the situation behind her. “I just wanted to get that out the way so I could move on with my music,” she told The Celeb Factory in 2011.

Ellen DeGeneres still thinks about these derogatory comments from her Diane Sawyer interview

In an ABC Primetime Live interview from 1998, Diane Sawyer spoke with Ellen DeGeneres, who had officially come out as gay a year earlier — an announcement that ultimately led to the cancellation of her sitcom, Ellen, on ABC just a year later. This was one of the few times that DeGeneres spoke about her sexuality publicly back then, and it was a groundbreaking interview in a lot of ways — but also a little uncomfortable.

Sawyer brings up the backlash that DeGeneres received afterwards, and reads some homophobic comments that had been shared in the wake of her announcement — including from the LGBTQ community who didn’t approve of the way that DeGeneres had chosen to come out about who she really is. One comment was from Elton John, saying, “Every program now is about lesbians. Shut up! Just be funny.” DeGeneres says the comments “hurt” her and she “wishes” they wouldn’t have been made publicly. 

Looking back, the whole situation certainly had a longterm impact on her. On an episode of Dax Shepard’s Armchair Expert podcast, DeGeneres recalled how that exact comment from John still stung, making it seem cruel in retrospect that Sawyer had brought it up at all. “I had never met him and I thought, ‘What kind of support is that from a gay person?'” she said, adding, “But everybody assumed I was just nonstop talking about it. … It hurt my feelings.”

Diane Sawyer interrupted Malala Yousafzai

As a young teen, Malala Yousafzai became known for her activism promoting education for girls where it was banned in her home country of Pakistan. In 2012, when she was just 15 years old, a Taliban gunman shot her in retaliation for her efforts. One year later, Yousafzai sat down with Diane Sawyer to talk about the experience, though the interview itself has been upsetting to some people who watched it.

“I️t really bothered me when Diane interrupted her while speaking and telling her brave story,” one YouTube viewer pointed out.

Although Sawyer largely received praise for the interview, critics also singled out the moment Sawyer asks Yousafzai if it was “wise” not to cover her face when she was approached by the gunman, which she had done in a show of bravery and how much she believed in the importance of female education. “[Sawyer] seems not to understand: It was necessary. The hero always finds the courage to do what is necessary,” another YouTube commenter wrote, adding, “‘Was it wise?’ No, it wasn’t wise, it was necessary.”

Malala’s response to the “wise” question is simple: “At that time, I wanted to live my life as I want.”

Did Diane Sawyer get too personal with Brad Pitt?

In 2005, Brad Pitt talked with Diane Sawyer while promoting his movie, Mr. and Mrs. Smith — the film where he famously met Angelina Jolie before he and Jennifer Aniston got divorced. In the interview, not only does Sawyer repeat claims that Jolie is a “homewrecker,” but she also pries further into Pitt’s split from Aniston and how Jolie might have been involved. “I’m a 41-year-old man, and I don’t see any need to defend myself,” Pitt says at one point in the interview when Sawyer tries to get too personal.

Other media outlets later called Sawyer out for her line of questioning when it came to Pitt’s personal life. “Pitt seemed resigned, even depressed, as he sipped ice water and squirmed in visible dread at Sawyer’s invasive and demeaning questions about his breakup with Jennifer Aniston,” a report from Slate published at the time said, pointing to a question about Pitt and Aniston disagreeing over having children.

Diane Sawyer's silence with Demi Moore became uncomfortable

A tried and true trick of the most seasoned interviewers is silence — not firing back with another question quickly to give the subject the opportunity to say things on their own they might not have otherwise in order to fill the silence. This is a tool that Diane Sawyer frequently uses, but in a 2019 Good Morning America interview with Demi Moore as she promoted her book, Inside Out, it became especially uncomfortable. 

In an interview where Moore discussed extremely personal things, including sexual assault, ex-husband Ashton Kutcher’s reported infidelity, and her difficult childhood, Sawyer read a passage of Moore’s book about falling in love with Kutcher, who was 15 years younger than her, out loud to her before sitting there silently, staring at her. Multiple YouTube commenters brought up how cringey the moment was, with one writing, “If i ever end up in a Diane Sawyer interview and she quotes me [then] stares at me, no question, no nothing. I’m just gonna stare right back at her.”

In this case, Sawyer’s strategy didn’t work; Moore broke the seemingly interminable silence simply by saying, “It’s all true.”

A weird editing choice had Diane Sawyer repeatedly interrupting Ashley Judd

When Ashley Judd was on Good Morning America in 2017 to tell her story about the sexual harassment she allegedly experienced at the hands of Harvey Weinstein, a curious editing technique was used that made it seem like Sawyer didn’t let a very clearly emotional Judd do much of the talking. It ended up causing some backlash with viewers, who objected to the use of Sawyer’s voiceover narration, which covered much of what Judd was saying. 

“I usually like Diane Sawyer’s interjections — they’re well placed and are aesthetically coherent with the larger interview, but man oh man was this irritating. Can you please let HER tell us the story?,” read one YouTube comment. “I hate how this interview was done and formatted. I’m shocked an interview by Diane Sawyer was so poor,” another added.

Judd hasn’t commented on whether or not she believes she was given enough of an opportunity to speak during what was her first TV interview about the case against Weinstein. The actor was, however, one of the first accusers to publicly speak out against the producer, who was eventually sentenced to 23 years in prison on counts of rape and criminal sexual acts.

Diane Sawyer got very personal with Jennifer Lawrence

After her success in The Hunger Games franchise, Jennifer Lawrence opened up to Diane Sawyer about her life in Hollywood on Nightline. It begins as a pretty lighthearted interview: Sawyer and Lawrence shoot a bow and arrow a la Katniss Everdeen, and look at photos from happy memories in the actor’s childhood. But even after Lawrence tries to shift the interview to the conversation about closing the wage gap between men and women, Sawyer brings up Lawrence’s personal plans for the future.

“I don’t know if I’ll ever get married,” a visibly unsettled Lawrence (who did, in fact, marry Cooke Maroney in 2019, four years after this interview) tells Sawyer, adding, “I don’t feel like I need anything to complete me.”

Some fans didn’t love the way Sawyer approached it, though, with one writing in a YouTube comment, “There is an undertone of this interview/media coverage that feels like the story of Diane Sawyer.”

Did Diane Sawyer's not press Chris Christie enough?

After former New Jersey governor Chris Christie was embroiled in a scandal nicknamed Bridgegate involving disruptive lane closures on the George Washington Bridge that were allegedly “on orders from high-ranking [New Jersey] officials,” he sat down with Diane Sawyer for ABC News after a report (which was conducted by lawyers he had hired on his own) proved that he wasn’t guilty of wrongdoing in the situation. In its entirety, the interview was awkward, since Christie seemed uncomfortable answering many of Sawyer’s questions, and at certain points, he even became combative, making the interview itself difficult to watch.

At the time, NJ Spotlight News accused him of selectively avoiding media over the scandal except for the chat with Sawyer, which it called it “a softball interview.” Salon went further, calling it a “pity party” in which “Sawyer came off as rather sympathetic” to Christie’s side of the story. Think that’s scathing criticism? The YouTube commenters showed even less mercy, with one particularly disgruntled viewer writing, “How does Diane Sawyer still have a job. That was the worst interview I think I have ever seen. Next time ABC should pick up a 5th grader at a local elementary school to do the interview.” Ouch. 

Was Diane Sawyer drunk on-air or just tired?

While this wasn’t an interview, it was another high-profile moment for the veteran anchor that had lots of people awkwardly gawking. As Diane Sawyer was covering the 2012 U.S. presidential election for ABC, some people believed that she was drunk on the air when she seemed to be slurring her words and mispronounced president Barack Obama’s name. This speculation got pretty wide coverage at the time; outlets including USA Today reported that, on multiple occasions, Sawyer made giggly mistakes she wouldn’t have made otherwise, and people on Twitter that night seemed to agree.

Later, while addressing the incident on Twitter, she seemed to brush the whole thing off. “Awe for the @ABC powerhouse team. Hail the techs who kept us on air during 25 minute power outage,” she wrote, adding in another tweet, “Read your tweets the good, bad, and the funny. See you on @ABCWorldNews.”

A source close to Sawyer told Business Insider that she wasn’t drunk, just tired from a busy work week. “It’s someone who was overworked because they do care so much about trying to put on quality coverage for the viewer and I think that it’s a symptom of her being a workaholic, not as many on Twitter defined to imply an alcoholic,” the source said. “That’s just crazy.”

Michael Jackson may have manipulated Diane Sawyer

In 1995, Michael Jackson and Lisa Marie Presley joined Diane Sawyer on Primetime Live, where he unequivocally shut down all claims that he had acted inappropriately with underage children. The interview became infamous; The New York Times later said Sawyer had “bungled” it, while Marie Claire noted that it was “strained.” But the same year, Vanity Fair fact-checked Sawyer’s reporting and found several incorrect statements she made on air.

Talking to the outlet, District Attorney Tom Sneddon said that Sawyer made a “glaring mistake” when she said that Jackson had been cleared of the allegations, and furthermore, the magazine reported that Sawyer interacted with Jackson and Presley ahead of their interview and even made special concessions for him so he’d be more comfortable. Sneddon also accused Sawyer of not challenging Jackson’s clearly false denials and claims, many of which Vanity Fair disproves with its own law enforcement and investigative sources. The Los Angeles Times also blasted the chat as “less an interview than an infomercial” and an example of “the media gleefully allowed themselves to be used.” 

In a statement to Vanity Fair, Sawyer said, “My interview was entirely in my hands. I decided what questions to ask. No one ever said to me, ‘Don’t ask that. Do ask that.’ I felt my primary mission was to cover the serious charges. If I didn’t get to some questions of Lisa Marie or the video, well, that’s that. The questions I wanted to ask were the serious questions.”

Lisa Marie Presley clearly wasn't feeling Diane Sawyer's Michael Jackson questions

In 2003, Diane Sawyer surprised a lot of people when she spoke to Lisa Marie Presley in a sit-down interview, asking her to explain why she would have married Michael Jackson in the first place. Even when Presley insisted there were parts of his personality that the public didn’t get to see and that she had been in love with him, Sawyer pressed further, asking how she could have been attracted to him.

Commenters on YouTube were astounded by Sawyer’s disbelief at Presley’s attraction to Jackson, with several calling the veteran interviewer “unprofessional” for the way she conducted the interview, and one even declaring, “Diane Sawyer’s reactions to Michael and Lisa’s relationship here border on racism.” Sawyer’s line of questioning even became so uncomfortable for Presley, she said, “I don’t want to keep talking about him. … I’m really not interested in going off on him.” Sawyer’s reply to that? “What about him and drugs?” Yikes.  

Though Jackson unexpectedly died at the age of 50 in 2009, his legacy has been called into question many times since then, including in the 2019 HBO documentary Leaving Neverland, which features the stories of now grown men who claim they were sexually abused by Jackson as children.

Diane Sawyer brought Donald Rumsfeld to tears, but no one bought it

Though this cringeworthy moment was certainly more on Donald Rumsfeld than it was on Diane Sawyer, it was still very awkward to watch. When he sat down for his first televised interview in years with Sawyer in 2011 for an ABC News World Exclusive, former Secretary of Defense Rumsfeld addressed the decision to go to war with Iraq after the Sept. 11, 2001 attacks in a way that wasn’t very impressive to viewers, since he didn’t seem to show any remorse for it.

At one point, Rumsfeld was even brought to tears, crying about his son’s battle with addiction, but many YouTube commenters believed that he was faking it, with one even pointing out that even Sawyer herself seemed to be “uneasy” during the interview.

In a later interview with Rumsfeld, a reporter from the Washington Examiner asked him if he had a problem with Sawyer’s questions, and at that point, “he shrugged” instead of giving a definitive answer, so it may have been true that the interview was awkward for everyone involved (including those of us at home, watching). 

The time Janet Jackson schooled Diane Sawyer on racism

During a 2001 Primetime Live interview with Janet Jackson, there were a couple of cringey moments on Diane Sawyer’s part. One big one? When Sawyer read some of the more risqué lyrics of Jackson’s song, “Would You Mind,” out loud to her, which seemed to make both of them uncomfortable. And it wasn’t just the fact that Sawyer awkwardly read the lyrics out loud — it was also that she seemed to use the moment to slut shame Jackson, asking her if this is something she reads to her mother.

Things got even worse when the conversation turned to race. When Sawyer mentioned that there are “tiny toxic darts” of racism that Jackson must face, Jackson laughed at the fact that she called them tiny, and then, Sawyer asked, “Do you think I’m completely incapable of understanding [racism]?” to which Jackson replied, “Yes, because you are on the other side.”

Jackson hasn’t commented on that exchange and neither has Sawyer — at least, not publicly. But she has remained outspoken about racism that Black people in America face, including in her performances.

Diane Sawyer clearly made Susan Boyle uncomfortable

In 2009, Susan Boyle made headlines when she stunned Britain’s Got Talent viewers with her voice. Her disarming personality won fans over before she went on to sell over 25 million records, and years later, revealed that she had been diagnosed with autism. During the height of her popularity, Boyle spoke with Diane Sawyer, who pressed her on her mental health and the bullying she faced in school as soon as the interview began.

When Boyle asks to move on from the topic of her bullies, Sawyer immediately asks about Boyle admitting that, at nearly 50 years old, she’s never been kissed. “No comment. I don’t want to talk about that,” Boyle says. And where does Sawyer go from there? Money! She basically asks Boyle what she’s going to buy now that she’s rich. “Well, it’s just baby steps at the moment. We shall see how things progress,” Boyle diplomatically answers. Even for a remote interview the awkward silences between Boyle’s curt answers and Sawyer’s stilted laughter were palpable. 

Shortly after the interview aired, The Cut accused Sawyer of being “patronizing” to Boyle, especially when she asked her if she wanted to get a makeover when she comes to the United States. As of this writing, neither woman appears to have spoken publicly about how they feel about the interview in retrospect.

Diane Sawyer gets physical with Dr. Oz

In a rare example of Diane Sawyer being on the receiving end of the cringe during a televised interview, this 2009 Good Morning America segment had the anchor placed in an uncomfortable position by Dr. Mehmet Oz. Controversial in his own right, as over the years some of his medical advice has been criticized by his peers as having no basis in fact, Oz is still a fellow ABC personality, so when it came time to promote the release of one of his books, Oz appeared on the morning show to talk about keeping the brain “young.”

At this point in the interview, Oz asks Sawyer to get out of her chair, and though she is wearing a skirt, asks her to complete an exercise with him that requires her to spread her legs. Sawyer is obviously uncomfortable, and it makes for a very awkward segment, eliciting laughter both on- an off-camera. 

Fortunately, it seems like they both got over it. In 2012, Oz and his foundation, HealthCorps, honored Sawyer for using her platform to promote childhood health and wellness at a gala event in New York.

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