Diane Sawyer is regarded as one of the most prominent TV journalists of our time.
And as it goes with such prominence, there are plenty of awkward moments on her rap sheet
of high profile interviews.
So without further ado, here are the most cringeworthy moments of Sawyer's career.
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, whereas Timberlake had
frequently addressed it in interviews, as well as released his hit 2002 single, "Cry
Me A River" - a song about the end of their relationship.
"You did something that caused him so much pain, so much suffering.
What did you do?"
Spears says that they were, quote, "both really young" and a breakup was inevitable.
Sawyer pushes even further, mentioning 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.
She responded that everyone has their own side to the story, and added:
"I'm not technically saying he's wrong, but I'm not technically saying he's right, either."
Spears even goes so far as to say, quote, "This feels really awkward right now."
The segment later sparked headlines that continue to this day.
In February of 2021, Buzzfeed claimed that viewers had once again become "enraged" by
the resurfaced line of questioning that they viewed as clear examples of, quote, "slut-shaming" and misogyny.
Another cringeworthy moment in Britney Spears' 2003 interview with Diane Sawyer comes when
Sawyer brings up how, quote, "Spears has upset a lot of mothers in this country" 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:
"Really, if I had the opportunity to shoot Britney Spears, I would."
Spears is understandably horrified, and calls the statement, quote, "really sad."
"I'm not here to babysit her kids"
She later adds 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 at
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 by the media.
On a February 2021 episode of The Talk, co-host Amanda Kloots even said:
"Diane Sawyer does owe [Spears] an apology."
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.
During Diane Sawyer's 2002 interview with Whitney Houston, she shows the singer photos
of herself, insisting that she is, quote, "scary thin."
Houston becomes visibly annoyed at the interrogation and even hands Sawyer the photos back.
However, this doesn't stop Sawyer from pressing her on rumors that she has an eating disorder
or uses drugs, which leads to Houston dropping a memorable line in response:
" 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 Washington Post wrote that the coroner's report
revealed her cause of death to be, quote, "drowning and effects of atherosclerotic heart
disease and cocaine use".
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."
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."
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.
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 lasting 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?'
But everybody assumed I was just nonstop talking about it [...] It hurt my feelings."
As a young teen, Malala Yousafzai became known for her activism promoting education for girls
in her home country of Pakistan - where it was banned.
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.
The interview has been upsetting to some people who have watched it.
One YouTube viewer said:
"I️t really bothered me when Diane interrupted her while speaking and telling her brave story."
Although Sawyer largely received praise for the interview, critics also singled out the
moment Sawyer asks Yousafzai if it was, quote, "wise" not to cover her face when she was
approached by the gunman, which she had done in a show of bravery.
Another YouTube viewer wrote:
"[Sawyer] seems not to understand: It was necessary.
The hero always finds the courage to do what is necessary.
'Was it wise?'
No, it wasn't wise, it was necessary."
Malala's response to the "wise" question is simple:
"I wanted to live my life as I want."
A tried and true trick of the most seasoned interviewers is silence - giving 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.
In this case, Sawyer's strategy didn't work; Moore broke the seemingly interminable silence
simply by saying:
"It's all true."
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.
One YouTube comment reads:
"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?"
Another added:
"I hate how this interview was done and formatted.
I'm shocked an interview by Diane Sawyer was so poor."
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 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.
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.
Lawrence is visibly upset, and says:
"I don't know if I'll ever get married, and I'm okay with that.
I don't feel like I need anything to complete me."
Some fans didn't love the way Sawyer approached it, with one writing in a YouTube comment:
"There is an undertone of this interview/media coverage that feels like the story of Diane Sawyer."
As it turns out, Lawrence married Cooke Maroney in 2019, four years after this interview.
You may remember when 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, quote, "on orders from high-ranking [New Jersey] officials".
After a report conducted by lawyers he had hired on his own proved that he wasn't guilty
of wrongdoing in the situation, he sat down with Diane Sawyer for ABC News to talk about it.
In its entirety, the interview was awkward, since Christie seemed uncomfortable answering
many of Sawyer's questions.
At certain points, he even became combative, making the interview itself difficult to watch.
"I think they love me in Iowa too, Diane.
I've been there a lot."
At the time, NJ Spotlight News accused him of selectively avoiding media over the scandal
except for the chat with Sawyer, which it called, quote, "a softball interview."
Salon went further, calling it a, quote, "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."
In 1995, Michael Jackson and Lisa Marie Presley joined Diane Sawyer on Primetime Live, where
Jackson 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, quote, "bungled"
it, while Marie Claire noted that it was, quote, "strained."
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, quote, "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.
"Okay, when you say 'boys', it's not just boys.
I've never just invited boys to come in my room.
Come on, that's ridiculous."
The Los Angeles Times also blasted the chat:
"The hour was less an interview than an infomercial.
[...] As always, 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."
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.
One viewer said:
"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."
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 abused by Jackson as children.
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 September 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, quote, "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 apparently shrugged
instead of giving a definitive answer, so it may have been true that the interview was
awkward for everyone involved — even for those of us watching from home.
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, quote, "tiny toxic darts" of racism that Jackson
must face, Jackson laughed, and the rest of the conversation went as such:
"Do you think I'm completely incapable of understanding what it is?"
"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.
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."
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."
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, quote, "patronizing"
to Boyle, especially when she asked her if she wanted to get a makeover when she comes
to the United States.
As of the making of this video, neither woman appears to have spoken publicly about how
they feel about the interview in retrospect.
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. Oz.
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.
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 a 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, quote, "embarrassed" and "humiliated" to see
the photos, Sawyer pushes on.
Fans on YouTube have accused Sawyer of victim-shaming and intentionally, quote, "going for tears,"
comparing this interview to the one she did with Britney Spears.
As for Rihanna herself, though?
Looking back, she saw it as an opportunity to put the situation behind her.
She told The Celeb Factory in 2011:
"I just wanted to get that out the way so I could move on with my music."
If you or someone you know is struggling with domestic abuse, please call or chat online
with the National Domestic Violence Hotline at 1-800-799-7233.