Whether you think you know everything about Britney or are just familiar with the headlines, the documentary is an eye-opening journey into the heart of pop darkness.
Here are six of the key takeaways from the special (streaming here on Hulu):
Felicia Culotta Has Been One of Britney's Truest Friends
In a business where friendship can often be transactional, Britney's long-time friend and personal assistant -- who worked with the singer from 1998 to 2007 and then again starting in 2009 -- reveals how she got pulled into the singer's orbit and became one of Brit's closest confidants. A fellow native of "tiny ... sleepy little town" Kentwood, La., Culotta -- who has been a family friend since Spears was 5 years old -- was asked to travel with Britney after she signed her first recording contract in 1998 so mother Lynne Spears could stay home to take care of her younger daughter, Jamie Lynn.
And while Culotta wasn't really a big sister or surrogate mother, her role quickly morphed from what she described as chaperone, to "partner" and finally assistant. One of the sweetest stories she tells is about the time when Spears' career was just taking off and the singer decided to do something nice for her hometown neighbors.
"One of the first things that she did when she just was getting famous was ... we were home for Christmas and she wanted to go get $10,000 in $100 bills, and she just drove through Kentwood and gave out $100 bills,” Culotta, who has a minor role as a teacher in the "Oops... I Did It Again" video, says in the doc.
Interviewers and Show Hosts Were Inappropriate and Tough on Spears
In archival footage from her run on Star Search in 1992, late host Ed McMahon asks the then 10-year-old singer, "I noticed last week, you have the most adorable, pretty eyes ... do you have a boyfriend?" When a polite Britney says "no sir," explaining that boys are "mean" to her, the nearly 70-year-old McMahon didn't let it go. "Boyfriends? You mean all boys? I'm not mean ... how about me?" The nervous pre-teen responds, "Well, it depends."
Later, an interviewer tells the teen singer, "Everyone's talking about it." When she asks what they were discussing, he says, "Your breasts," seemingly in reference to rumors that Spears had gotten an enhancement.
In a 2003 interview with ABC's Diane Sawyer, the veteran newswoman confronts Spears -- who was near tears -- about what she "did" to break former beau Justin Timberlake's heart. Sawyer then cues up a particularly cruel piece of tape that reportedly chronicles how worked up some moms around the country were about Britney's sexualized presentation. “Britney Spears has upset a lot of mothers in this country, starting with the wife of the governor of Maryland,” Sawyer says, cutting to audio from Kendel Ehrlich, who says of the 22-year-old star, "Really, if I had an opportunity to shoot Britney Spears, I think I would.”
Spears appeared unprepared and shocked by the tape. "Oh, that’s horrible! That’s really bad,” she responded. Sawyer doubled down, trying to imagine what Erhlich was thinking. "Because of the example for kids, and how hard it is to be a parent," Sawyer said. Seemingly sympathizing with the rough year Spears has had, Sawyer asked her how she feels about her public split and all the drama, to which Spears responded, "It was pretty rough ... yeah ... oh my goodness, hello! Eww ... strong Britney, yeah it was a weird time," she said as she burst into tears and asks for the cameras to be turned off.
Spears' rise is paralleled with the exploding scandal over former White House intern Monica Lewinsky's affair with President Bill Clinton and the ensuing tabloid coverage, which the documentary says bled over into rampant speculation about teen Britney's sex life. "Am I a virgin?" Britney responds to a question about her relationship with Timberlake. "Yes, I am virgin and I definitely want to try and [not] have sex until I'm married."
Timberlake Wasn't a Gentleman After Their Breakup
From the time the two former Mickey Mouse Club stars reportedly began dating in 1999 until their public breakup in 2002, the documentary describes the fevered speculation about whether they'd had sex or if she -- as rumored -- had cheated on JT. The doc delves into Timberlake's "Cry Me a River" video, which furthers the narrative of the alleged infidelity by casting a Britney look-alike.
"It really seemed like he took control of the narrative," said former MTV VJ Dave Holmes of the time after the pair's breakup. Added the Times' Wesley Morris: "He essentially weaponizes the video [for 'Cry Me a River'] to weaponize the relationship." And during the Star and Buc Wild Morning Show around that time, one of the hosts asks Timberlake, "Did you f--- Britney Spears?" which leads to some laughter and Timberlake responding enthusiastically, "Oh man ... OK, I did it!"
“What can you say about misogyny?" says Morris. "There’s a whole infrastructure to support it and when it’s time for people to come -- in a misogynistic culture -- for a woman, there’s a whole apparatus ready to do it.”
Jamie Spears Was Involved Early On, Then Faded and Returned With the Conservatorship
In the documentary, Britney's parents are described as sparing no expense to help her career take off, even when they didn't have the money, with mom Lynne traveling back and forth by train to New York to help her daughter make it. Jamie, described by the Times as "not around very" much when Britney was growing up, struggled with alcohol -- and reportedly later going to rehab -- is said to have tried his hand at being a cook, construction and opening a failed gym before filing for bankruptcy. "He doesn't appear to be a big presence in her life," with former label marketing exec Kim Kaiman saying she'd hardly ever spoken to Jamie, who once bragged, "My daughter's so rich she's going to buy me a boat."
While seemingly uninvolved in Spears' life during her peak years, Jamie re-emerges in 2007 to take control of his daughter's life after what the Times describes as a period when it was believed the singer was suffering from mental health issues and possible drug dependence. Since early 2008, he has been conservator of her person as well as her estate. The arrangement is so tight, the Times reports, that it controls who can and can't see the singer and calls for 24-hour security guards, as well as giving the conservators access to her medical records and discussions with her doctors, the power to cancel her credit cards and make recording and touring deals on her behalf.
While Spears would stabilize and go on to release the albums Circus (2008), Femme Fatale (2011), Britney Jean (2013) and Glory (2016) and mount a wildly successful Las Vegas residency, an attorney who worked with the family at the time of the conservatorship says Britney used "sound judgement" in declaring that she realized she wouldn't be able to avoid the conservatorship. But it was the second thing she said that struck him: "I don't want my father to be the conservator."
Britney Appeared in Control of Everything -- Until She Wasn't
At one point, as her career is taking off, the documentary notes that Spears was a pitchwoman for Pepsi, Clairol, Polaroid and milk while selling an astronomical 20 million-plus albums. "I know all the ins and outs of what I'm doing," she tells an unseen interviewer. "I know about all the contracts and all the deals I'm about to do, I'm not just some girl who's listening to my manager."
Former backup dancer/tour director Kevin Tancharoen said Spears was focused and "definitely in control of a lot of decisions ... that idea that Britney is a puppet who just gets moved around and told what to do is incredibly inaccurate." Tancharoen added that during his run with the singer from 1999 to 2004, her team would present ideas to Spears and she needed to like and approve them, describing her as "very creative" and definitely "the boss."
"That's where I am today, because I do have control," she tells an interviewer who asks how the singer handles those around her trying to make all the decisions for her. By 2004, Spears says in an interview she sees herself as a married mom with kids who does music on the side in her future, just before she marries dancer Kevin Federline. The early narrative starkly contrasts with the second half of the documentary, which focuses on the complete lack of control she has over her own decisions and life under the conservatorship.
The Rise of Paparazzi Culture Went From Bad to Scary
When celebrity tabloid photographers began getting aggressive around 2004, one snapper says at first Britney seemed to enjoy the attention. "She was very friendly, a sweetheart of a girl. It was like she needed us, and we needed her, we both needed each other and it was a great kind of relationship," he says. But after Spears announced her first pregnancy, the attention goes into overdrive, and the documentary shows an increasingly stressed, frightened-looking Britney trying to get from one place to another while cradling her son's head as reports surface insinuating that she's a bad mother.
In a 2006 interview with Matt Lauer about the paparazzi culture, Spears says her father used to drive around with her on his lap, just like she was pictured doing by the paparazzi. "Is Britney a bad mom?" Lauer says people are asking. "Hmm ... that's America for you," Spears responds with a sigh.
The documentary also dives into what is described as her "unraveling" in public, with a flood of images and videos that show Spears in an unflattering light as throngs of photographers and videographers blind the singer with their flashes and dog her every step. Often weepy and sometimes looking wooden, Spears appears aghast as the photogs literally fight amongst themselves for the money shot, telling them, "I'm scared, I'm scared," as they descend on her before lunch at a restaurant and crush in around her car.
"What do you think it will take to make the paparazzi leave you alone?" Lauer asks. "I don't know ... I don't know," a sad Spears responds. Lauer asks, "Is that one of your biggest wishes?" Britney, looking down as she tries to stifle tears, whispers, "Yeah."
The paparazzi frenzy reached its apex in 2007 when Spears famously visits a Los Angeles salon. There, after a stylist refuses to shave her head, Britney does it herself, then bashes a pap's car with an umbrella.