Diane Sawyer's Most Controversial On-Air Moments That Tarnished Her Legacy

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Once upon a time, Diane Sawyer was considered the go-to for honest and hard-hitting interviews that left no stone unturned. However, as the years went by, we began wondering whatever happened to Diane Sawyer since her interviews were suddenly quite few and far between. The veteran reporter's scarce TV appearances should have arguably come as no surprise, though, since she announced that her time as ABC News' flagship anchor had ended in 2014. In a statement shared by The Guardian, Sawyer made it clear that she had no plans to say farewell to television altogether, clarifying, "I'll be joined by an incredible team of journalists dedicated to enterprise reporting, innovative approaches to breaking news and new ways of thinking about big issues and events around the world." 

The move worked in the network's favor since The Washington Post subsequently reported that Sawyer's hit show "World News Tonight" had seen a significant ratings boost ever since David Muir took over the reins from her. Meanwhile, one of the richest news anchors in the U.S. stayed true to her word and expanded her journalistic horizons while continuing to have candid chats with big names. 

In fact, Sawyer was one of the last people to interview the late Matthew Perry before his untimely passing in 2023. In May 2025, she had a hard-hitting chat with Kelsey Grammer about his 18-year-old sister's murder. However, her interviews since stepping down have been noticeably tamer with Sawyer taking a more empathetic approach with her subjects across the board. Although it's difficult to pinpoint the reason for the change, there's a chance that Sawyer wants to avoid the backlash she has received in the past because of her controversial interview moments.

In 2003, Diane Sawyer questioned Britney Spears about how she was handling the media fallout from her breakup with Justin Timberlake the previous year. Although the "Toxic" hitmaker tried to put her complex feelings into words, she ultimately broke down. However, that emotional display evidently didn't compel the experienced interviewer to go easy on her because she repeatedly brought up her negative public image. Among other things, Sawyer detailed how Timberlake had painted Britney out to be a cheater who had broken his heart, apparently to force her to address the rumors head-on. 

However, the iconic pop star refused to either confirm or deny the infidelity rumors. At one point, the Grammy winner even urged her to move past the sensitive topic, but Sawyer pressed on and asked specifically about the "Cry Me A River" music video. Elsewhere in their chat, the controversial journalist also crossed a line and questioned if she would urge her younger sister, Jamie Lynn Spears, to practice celibacy until marriage since she didn't do it herself. And to top it all off, she also questioned how Britney could continue to cater to a younger fanbase while rebranding herself as an adult performer.

In her 2023 memoir, "The Woman In Me," Britney admitted that her sit-down with Sawyer changed her, writing, "I felt like I had been exploited, set up in front of the whole world." She continued, "That interview was a breaking point for me internally — a switch had been flipped. I felt something dark come over my body" Following the book's release, the 2003 interview with Sawyer resurfaced online and upset Britney's fans greatly.

In 2009, Rihanna appeared on "20/20" to open up about her abusive relationship with Chris Brown. However, the interview took a rather insensitive turn when Diane Sawyer showed her the photo that TMZ had shared of her face after Brown physically assaulted the singer, and asked Rihanna how she felt about it. "I get very embarrassed. I feel humiliated, I get angry all over again. Every time I see it, the whole thing plays back in my head," the "Diamonds" hitmaker confessed in response (via YouTube). 

Elsewhere, Sawyer also wondered whether Rihanna had done anything to bring about Brown's abuse, echoing the sentiments of people who didn't believe her story. In response, the Grammy winner clarified that she hadn't provoked him, proclaiming that even if she had, she didn't deserve to be physically assaulted for it. Many commentators under the YouTube video called Sawyer out for intentionally asking questions that would elicit tears from the singer. Sadly, that wasn't the only time her line of questioning bothered viewers. 

In 2003, Sawyer sat down for a chat with Lisa Marie Presley and repeatedly questioned how she could have fallen for a man like Michael Jackson. Even after Presley detailed how she grew fond of the pop titan after learning that he wasn't like the media made him out to be, Sawyer demanded to know whether she was sexually attracted to him. At one point, Presley asserted that she had no desire to talk about her second ex-husband negatively, but Sawyer didn't let up, turning her attention to his alleged drug use instead.

Diane Sawyer's 2002 ABC News sit-down with Whitney Houston started out on an invasive note when the interviewer presented the "I Will Always Love You" hitmaker with a photo of her performing and asked if the rumors of her eating disorder were true. Although Houston confirmed that her weight fluctuated because stress affected her eating habits, Sawyer just wouldn't let up, asking about the growing speculation that drug use was to blame. After the journalist read a headline claiming she was using crack cocaine, the iconic singer seemed annoyed as she clapped back, "Crack is cheap."

Houston continued, "I make too much money to ever smoke crack. Let's get that straight. Okay? We don't do crack. We don't do that. Crack is whack." Although Sawyer's questions were undoubtedly controversial, and even rude, the interview is still considered iconic because of how deftly Houston tackled them. In fact, Janet Jackson took a similar approach to dealing with an uncomfortable Sawyer interview. 

When the "All For You" hitmaker sat down for a chat with the journalist in 2001, she read out the sexually explicit lyrics of her track "Would You Mind?" However, Jackson didn't appear fazed and smiled as Sawyer tried to poke fun at her. Years later, many Redditors were impressed by how coolly the Grammy winner handled the weird situation. However, that wasn't the only odd moment to come out of the interview since Sawyer also asked Jackson if she didn't think she could understand racism, and received: "Yes, because you're on the other side" in response (via YouTube).

In 1995, Michael Jackson and Lisa Marie Presley sat down with Diane Sawyer to discuss the allegations that he had behaved inappropriately with the children who stayed over at his Neverland compound. The infamous interview left viewers deeply divided. On the one hand, some found that Sawyer had gone far too easy on the "Thriller" hitmaker and hadn't fought back against some of his supposedly factually incorrect answers. For instance, in a chat with Vanity Fair, San Francisco District Attorney Tom Sneddon argued that Sawyer had made a grave mistake by claiming that Jackson had "been cleared of all the charges." The DA clarified that that simply wasn't the case, adding, "The state of the investigation is in suspension until somebody comes forward." 

Likewise, he pointed out that the "Smooth Criminal" singer's assertion that there wasn't any evidence to back up the claims wasn't accurate either. However, when Jackson mentioned it in the interview, Sawyer didn't do much to dispel his answer. Meanwhile, another group felt that she had manipulated the King of Pop with her probing questions. One commentator took to X, formerly known as Twitter, to share a clip of Sawyer questioning his decision to settle the lawsuits outside of court, despite claiming he was innocent. 

How in the HELL do you piss off Michael Jackson? Diane Sawyer displayed unethical journalistic practices by asking Jackson questions that had no basis in reality, but used as a tactic to prejudice the viewers. Lisa Marie Presley was here to set the record straight. pic.twitter.com/WBDdpDki92

— Dr. Andrew Greene (@AndrewGreene864) February 9, 2021

"Diane Sawyer displayed unethical journalistic practices by asking Jackson questions that had no basis in reality, but used as a tactic to prejudice the viewers," they posited. Another critic shared the same belief based on the veteran reporter's questions about whether he would continue to bring children to Neverland even after the allegations were made public.

Jennifer Aniston had a complicated relationship with her parents. In 1999, her mother, Nancy Dow, released her memoir, "From Mother And Daughter To Friends" to detail how their complex dynamic eventually spiraled into full-on estrangement. Naturally, the book was a sensitive topic for the "Friends" star. However, that didn't stop Diane Sawyer from presenting Aniston with a page from it during their 2004 interview. It brought tears to the actor's eyes, as she admitted, "I never looked at it," (via YouTube). 

The Emmy winner then continued crying while Sawyer read out some of the positive things she had publicly said about Dow in the past. After Aniston reiterated that she still stood by her words even though her mother had made some mistakes, the interviewer charged on, demanding to know if she felt any remorse about her seeming inability to mend fences. Several YouTube commentators slammed Sawyer for being insensitive and praised the "Morning Show" star for how she handled her probing questions. 

While Aniston remained kind and steady in her responses, her ex-husband, Brad Pitt, took a very different approach the next year. At one point during their super awkward 2005 chat, Sawyer indirectly tried to get the Oscar winner to address the speculation that he had cheated on Aniston with Angelina Jolie. Pitt curtly answered, "I'm a 41-year-old man, and I don't see any need to defend myself," (via YouTube). Many YouTube users found the famed interviewer's questions sexist because she repeatedly tried to paint Jolie as a homewrecker instead of putting the onus on Pitt for his reported wrongdoings.