Why Britney Spears Considers "Harsh" 2003 Diane Sawyer Interview a "Breaking Point"

Britney Spears is reflecting on a painful moment that was broadcast for all to see.

In her memoir The Woman in Me, the "Toxic" singer recalled her now-infamous 2003 interview with Diane Sawyers, in which the journalist confronted Britney about her then-recent breakup with Justin Timberlake, as well as whether the pop star was behaving in a way to be a good role model for children. In fact, the line of questioning brought the then 21-year-old to tears in her own home. 

"I'd often retreated to my apartment to be alone," Britney wrote of the period after her public split with the *NSYNC member in 2002. "Now I was being forced to speak to Diane Sawyer there and cry in front of the entire nation."

And when it came to the interview itself, the Crossroads actress described it as "completely humiliating."

"I wasn't told what the questions would be ahead of time, and it turned out they were 100 percent embarrassing," she continued. "I was too vulnerable then, too sensitive, to do this type of interview. I didn't want to share anything private with the world. I didn't owe the media details of my breakup. I shouldn't have been forced to speak on national TV, forced to cry in front of a stranger, a woman who was relentlessly going after me with harsh question after harsh question."

And in looking back, the now 41-year-old can see how the interview left its mark on her.  

"I felt like I had been exploited, set up in front of the whole world," Britney wrote. "That interview was a breaking point for me internally—a switch had been flipped. I honestly feel like that moment in my life should have been a time for growing—and not sharing everything with the world. But I had no choice. It seemed like nobody really cared how I felt."

E! News has reached out to reps for Diane for comment but has not yet heard back.

The 2003 interview resurfaced in 2021 after it was featured in the 2021 New York Times documentary Framing Britney Spears. And when revisited under a new lens nearly two decades later there was outcry over Diane's treatment of Britney as well as calls for her to apologize, though the journalist never did so publicly.

In addition to her interview with Diane, Britney gives an intimate look inside her rise to superstardom and subsequent 13-year conservatorship in The Woman in Me, detailing her relationship with Justin and sharing she had an abortion after becoming pregnant with Justin's baby and reflecting on asking her sister Jamie Lynn for help amid as she sought her freedom.

For more of the memoir's biggest bombshells, keep reading. 

Britney Spears met Justin Timberlake when they were Mouseketeers on Disney Channel's The Mickey Mouse Club in the early 1990s along with Christina Aguilera and slightly older talents including Keri Russell, Ryan Gosling and Tony Lucca.

Though it would be some years before they dated, falling for each other when she went on tour with *NSYNC, Britney writes that she and Justin shared their first kiss while playing Truth or Dare during a cast sleepover with—insert irony here—a Janet Jackson song playing in the background.

Among the devastating low points Britney describes about dating Justin, she shares that she had a medical abortion because his position was that they were both too young to become parents. She underwent the process at home, she writes, recalling Justin lying on the bathroom floor with her and strumming his guitar during what she calls "one of the most agonizing things I have ever experienced in my life."

She still isn't sure if she made the right choice, adding, "If it had been left up to me alone, I never would have done it. And yet Justin was so sure that he didn't want to be a father."

E! News reached out to Justin's rep and did not immediately hear back.

But as various Justin-centric anecdotes in Britney's book made headlines ahead of its release, a source shared that the 42-year-old is working on new music, plus he and wife Jessica Biel are feeling great and keeping busy with sons Silas, 8, and Phineas, 2.

According to Britney, Justin is in the club of celebrities who've ended relationships with the equivalent of a digital Post-It.

She was so "devastated," she recalls, she "could barely speak for months."

Britney went back home to Kentwood, La., to recover—and, post-breakup, she writes, Justin flew out there to personally deliver a letter he wrote and had framed that concluded, "I can't breathe without you."

Recalling the insinuations in Justin's "Cry Me a River" video that she had cheated on him, Britney writes of having to deal with the fallout, feeling "comatose in Louisiana" while her ex was "happily running around Hollywood."

She points to her cringe-inducing November 2003 interview with Diane Sawyer, arranged by her father and manager, in which the journalist grilled her about the pain she supposedly caused Justin as her "breaking point."

"I felt like I had been exploited," she writes, "set up in front of the whole world."

As was rumored years ago, Britney admits to making out with dancer-choreographer Wade Robson at a bar one night while she was dating Justin. But she attributes the gossip that Justin was cheating on her for pushing her into that mindset.

Otherwise, she writes, she was faithful to Justin.

Britney maintains that, during the days when it looked like she was partying hard with Paris Hilton, Lindsay Lohan, et al., she didn't have a drinking problem, but used the ADHD medication Adderall to get high and enjoy "a few hours of feeling less depressed."

It wasn't much of a secret 20 years ago that something was going on between Britney and Colin Farrell, and she describes their fling as a physically intense couple of weeks.

"Brawl is the only word for it—we were all over each other, grappling so passionately it was like we were in a street fight," Britney writes.

However, she admittedly wasn't "over Justin" when she was Colin's date to the Jan. 28, 2003, premiere of The Recruit, where the Irish actor told reporters they were "just mates" and not dating, but "she's a sweet, sweet girl."

Britney writes in The Woman in Me, "But for a brief moment in time, I did think there could be something there. The disappointments in my romantic life were just one part of how isolated I became. I felt so awkward all the time."

E! News has reached out to Colin's rep for comment but did not hear back.

Britney was bored and "just honestly very drunk," she writes, when she and childhood friend Jason Alexander swapped vows in Las Vegas in January 2004. The union was annulled 55 hours later.

She marveled over her family's reaction—"like I'd started World War III"—but it was "innocent fun" as far as she was concerned.

(Meanwhile, Jason was arrested and pleaded no contest to trespassing on Britney's more consequential wedding day when she married Sam Asghari at home on June 9, 2022.)

The unforgettable night in February 2007 when Britney walked into a Los Angeles-area salon and buzzed all her hair off was a response to the constant objectification she'd been subjected to since coming of age in the spotlight. (She notes elsewhere in the book that she went on Prozac around the time Oops...I Did It Again was blowing up to deal with the heightened scrutiny.) 

"I'd been looked up and down, had people telling me what they thought of my body, since I was a teenager," she writes. "Shaving my head and acting out were my ways of pushing back."

She was also "out of my mind with grief" while locked in a custody battle with ex-husband Kevin Federline over their sons, Sean and Jayden (who are now 18 and 17).

"Flailing those weeks without my children, I lost it, over and over again," she recalls. "I didn't even really know how to take care of myself." She famously smacked a paparazzo's car with an umbrella, her new haircut adding to the drama of it all, and remembers her thought process at the time growing increasingly childlike while she was still "in the throes of severe postpartum depression" and dealing with the end of her marriage.

Kevin was later granted sole physical custody of their kids on Oct. 1, 2007.

Britney was placed in a conservatorship on Feb. 1, 2008—initially after a series of emergencies, including the star being put on two 5150 holds in January 2008, but then it was extended indefinitely.

The "...Baby One More Time" singer recalls that she "begged the court to appoint literally anyone else" than her father, Jamie Spears, as her conservator. (Lawyer Andrew Wallet was co-conservator until March 2019.)

But she says she gave up the legal fight to free herself early on so she could be reunited with her kids as soon as possible.

"My freedom in exchange for naps with my children—it was a trade I was willing to make," she writes. "There is nothing I love more—nothing more improtant to me on this earth—than my children. I'd lay down my life for them."

Britney describes the alleged confines of the conservatorship as being too "sick to choose my own boyfriend and yet somehow healthy enough to appear on sitcoms and morning shows, and to perform for thousands of people in a different part of the world every week!" 

Eventually, Britney writes, she "began to think that [dad Jamie] saw me as put on the earth for no other reason than to help their cash flow."

She alleges she wasn't even allowed to change her set list when she wanted to during her wildly successful Las Vegas residency at Planet Hollywood. 

"My music was my life," she writes, "and the conservatorship was deadly for that; it crushed my soul."

Jamie, who took some time away from being co-conservator in 2019 while he dealt with health issues and then stepped down for good in September 2021, has stated multiple times in the past that he believed the decisions he was making were in Britney's best interest.

From her portioned-out medication to the settings on her iPhone, Britney writes, "Everything was scrutinized and controlled. Everything."

Including, she alleges, her weight. "If I thought getting criticized about my body in the press was bad, it hurt even more from my own father," she writes. "He repeatedly told me I looked fat and that I was going to have to do something about it."

While she was notably silent about the circumstances of her life during most of the 13 years she spent in the conservatorship, Britney alleges she did try to say something...once.

"I even mentioned the conservatorship on a talk show in 2016," she writes, "but somehow that part of the interview didn't make it to the air. Huh. How interesting."

During what Britney describes as her involuntary trip to rehab in early 2019—"My father said that if I didn't go, then I'd have to go to court, and I'd be embarrassed," she writes—she recalls being prescribed lithium and being kept there "against my will" for months.

"I couldn't go outside," she continues. "I couldn't drive a car. I had to give blood weekly. I couldn't take a bath in private. I couldn't shut the door to my room."

From the facility, Britney texted Jamie Lynn Spears, pleading for help, she writes. Her little sister's response, per the book, was, "Stop fighting it. There's nothing you can do about it, so stop fighting it."

Britney felt betrayed, writing, "I didn't understand how Jamie Lynn and our father had developed such a good relationship. She knew I was reaching out to her for help...I felt like she should have taken my side."

In early 2022 the siblings publicly sparred over Jamie Lynn's memoir, Things I Should Have Said.

Jamie Lynn "rushed out salacious stories about me, many of them hurtful and outrageous," Britney reiterates in her book. But, she concludes, she loves her sis, adding, "I'm working to feel more compassion than anger toward her and toward everyone who I feel has wronged me. It's not that easy."

E! News has reached out to Jamie Lynn for comment. She said on E!'s Daily Pop in 2022 that she and Britney "go back and forth, but at the end of the day, the love and support will always be there."

Britney notes that it was during her 2019 rehab stay that she first saw YouTube clips, courtesy of a nurse at the facility, alerting her to the existence of the unofficial but vigilant #FreeBritney movement.

As the years went by and the public discussion around whether she still should be in a conservatorship intensified, Britney kept up with the news.

"Seeing the documentaries about me was rough," she writes. "I understand that everyone's heart was in the right place, but I was hurt that some old friends spoke to filmmakers without consulting me first." She adds, "There was so much guessing about what I must have thought or felt."

When Jamie was removed as co-conservator in September 2021, "I felt relief sweep over me," Britney recalls. "The man who had scared me as a child and ruled over me as an adult, who had done more than anyone to undermine my self-confidence, was no longer in control of my life."

She was at a resort in Tahiti on Nov. 12, 2021, when her lawyer called to tell her a judge had terminated the conservatorship entirely.

Britney relishes being free to post whatever she wants on social media now, including the occasional strategically censored nude selfie. 

 "I know that a lot of people don't understand why I love taking pictures of myself naked or in new dresses," she explains. "But I think if they'd been photographed by other people thousands of times, prodded and posed for other people's approval, they'd understand that I get a lot of joy from posing the way I feel sexy and taking my own picture, doing whatever I want with it."

Britney writes that she has suffered "physical and emotional damage" from being in the conservatorship, and still gets migraines.

"I don't think my family understands the real damage that they did," she writes.

But she doesn't take freedom for granted, whether that means "taking a break from Instagram without people calling 911" or "being able to make mistakes, and learning from them."

It means "I don't have to perform for anyone—onstage or offstage," she writes. "Freedom means that I get to be as beautifully imperfect as everyone else. And freedom means the ability, and the right, to search for joy, in my own way, on my own terms."