All the WTF Moments From Britney Spears' 2003 Sitdown With Diane Sawyer

In the wake of Framing Britney Spears, we're reexamining the 2003 sitdown that’s earning the seasoned journalist a healthy heaping of backlash.

By Tierney Bricker Feb 12, 2021 11:00 AMTags

"Britney Spears, America's most famous paradox in pink."

That was how Diane Sawyer referred the then 21-year-old Britney Spears during their 2003 interview. And that primetime conversation is making headlines almost two decades after the two women sat down together because of its inclusion in "Framing Britney Spears," the Feb. 5 episode of FX's docu-series, The New York Time Presents which—in addition to examining the #FreeBritney movement—shines a light on the media's treatment of the 39-year-old pop star.

Diane's discussion with Britney is shown several times during the documentary, with viewers criticizing the journalist's handling of questions about the demise of Britney's relationship with Justin Timberlake, by asking-slash-accusing, "What did you do?" and the singer's responsibility to be a role model to young women. 

Since "Framing Britney Spears" premiered, critics have flooded Diane's Instagram accounts with comments about her treatment of Britney during that interview and demanding an apology.

Naturally, we decided to go back and watch the hour-long intimate interview to see if the few clips included in the episode were indicative of the overall tone of the special.

And in a word: Yep.

Diane's line of questioning was often patronizing and seemingly in pursuit of getting Britney, who was promoting the release her "In the Zone" album, to break down, eventually bringing the entertainer to tears.

"Framing Britney Spears'" Most Disturbing Moments

Here's a rundown of all of the moments that raised our eyebrows and left us slack-jawed while watching the infamous 2003 sitdown interview...

That Belly Button Montage

What better way to open an in-depth sit-down with the world's most famous pop star than by welcoming in viewers with these 15 words: "Ladies and gentlemen, the most valuable square inch of real estate in the entertainment universe," then playing a 10-second photo montage of Britney Spears' stomach? 

An odd way to kick off the conversation, to be sure. Particularly when you consider they used provocative images of Britney's body to set up Diane Sawyer's line of questioning about the singer's "provocative" image. About that...

Shock and Awe

Holding up several magazine covers and images from photoshoots in front of Britney, Diane bluntly asked, "What happened to your clothes?"

After Britney attempted to laugh it off by explaining, "I have clothes on now!" Diane, feeling almost like a principal admonishing a student, continued, "No kidding, what's this about? Is it about shocking people?"

Explaining that she felt "comfortable in her own skin" and that "it's an OK thing to express yourself," Britney then pointed to some of her peers as examples of other women posing in a similar manner without receiving the same treatment. 

"I hate to bring this up, but Kate Hudson, she's 22, she's in sheets," the "Toxic" singer noted. "Jennifer Lopez poses very provocatively sometimes. Christina Aguilera, what's the big deal when I do it? [Laughs.] Like, come on!"

The big deal, according to Diane, was the belief that "everybody always thought you had a different relationship to young girls." In a later voiceover, the ABC anchor really dug in, stating, "The girls who always played it close to the line on how much skin she showed, posed in this for Esquire magazine. Consider the line officially crossed."

The Leading Question

After Britney defended several images of herself on various magazines, including the previously mentioned Esquire cover and Rolling Stone, Diane asked, "Have you ever gone further than you wish you had?"

While Britney initially said she hadn't, Diane had a photo at the ready, one from the Esquire photoshoot where her breasts are covered by strings of pearls. "That is one picture, I must say, where I felt kind of weird about," Britney finally relented, with Diane pushing further, asking, "Wish you hadn't done it?"

After saying she did regret taking the photos "a little bit," Britney added, "But hey, it's done and I'll learn from it and I'll never be put in that position."

A voice-over from Diane then claimed Britney kept "getting burned by the fire she lit herself."

The Justin of It All

"You did something that caused him so much pain…so much suffering. What did you do?"

That's how Diane begins the much-hyped conversation about Britney's breakup with Justin Timberlake, putting the "Sometimes" singer in the hot seat. "I was upset for a while. We both are really young and it was kind of waiting to happen," Britney explained of ending their three-year romance. "I will always love him…he is such a great person."

Diane then pressed Britney to admit any wrongdoing—"He's left the impression that you weren't faithful…that you betrayed the relationship"—before asking her what lesson she learned from the phone call she received from Justin about the "Cry Me a River" music video, which starred a Britney look-alike being followed by Justin. While he gave her a heads-up, Britney explained she wasn't exactly prepared to see their breakup recreated by her ex.

Setting an Example

Arguably one of the most appalling moments of the sit-down comes when Diane addressed the wife of Maryland's then-governor claiming, "Really, If I had an opportunity to shoot Britney Spears, I think I would."

When Britney expressed shock and sadness over the statement, Diane tried to reason, "Because of the examples for kids and how hard it is to be a parent and keep all of this away from your kids."

Diane later impressed upon Britney what she felt was her responsibility as entertainer. "It's one thing to not want to be the role model anymore," she said. "It's another thing not to know that a lot of young girls are looking at this…a lot of them."

And then there was this question, alluding to the way she dressed and performed at the time, especially her infamous on-stage kiss with Madonna at the 2001 MTV Music Video Awards: "Do you get to have it both ways, you know, 'I'm not that innocent' or are you that innocent?"

Addressing Addiction

In an odd follow-up to Britney talking about not feeling comfortable spending a lot of money on certain items because of the way she was raised, Diane asked of her shopping habit, "Is it an addiction?"

Surprised, Britney repeated the question back before answering, "No, I don't think it's an addiction. It makes me happy. No, it's not an addiction!"

Later, Diane dealt with reports claiming the singer was doing drugs by peppering Britney with inquiries about what illegal substances she had or had not taken. 

Vocal Unrest

"Do you like your voice?"

Less than five minutes into the interview, Diane posed that question to Britney, who thoughtfully responded to the blunt inquiry clearly alluding to criticism of her vocal talent.

"I'll be completely honest, I think my voice is OK," Britney admitted. "I like the feeling that I get when I sing. It's not so much my voice, it's a state that I go in when I sing that I really like. But I would love to have a voice like Christina [Aguilera]. I would love to have a voice like Whitney Houston. I love their voices."

Nervous Tics

As she asked extremely personal and direct questions throughout the interview, Diane also pointed out what she saw as Britney's anxious habits.

"She still frightens herself with worst-case scenarios and constantly bites her nails to the quick," a voiceover stated before Diane inspected Britney's fingernails for herself, assessing that they didn't look bitten down. "That's because I have false nails on right now," Britney whispered in return. 

Later, Diane has the editor rewind and then play back footage of Britney subconsciously popping her knuckles.

Body Talk

While she may have had issues with Britney displaying her body in photoshoots, Diane didn't seem to mind asking about her "world-famous" physique, including just how many crunches she does to get her toned abs. "You're not working on them all the time?"

After Britney commented that she wasn't in the "best shape" at the moment, but "wasn't self-conscious about it" and would resume her routine once she goes on tour, Diane asked in a voiceover, "Then will she have the perfect body? Not to her."

She then asked Britney, "You don't like the bottom? The world-famous?"  

Framing Britney Spears is available on Hulu.

For everything you should be watching right now, don't miss BingE! Club hosted by Erin Lim on Snapchat!