The Most Haunting Moments of “Framing Britney Spears”

“Framing Britney Spears,” the Feb. 5 episode of the FX docu-series The New York Times Presents, goes back to the beginning to explain how Britney, one of the most famous women in the world and one of the defining pop stars of a generation, ended up, at the age of 39, in this situation, as well as the increased efforts she has started taking in recent years to extricate herself from it.

And while there’s only time for the bullet points of the “Oops…I Did It Again” singer’s rise from Star Search phenom and New Mickey Mouse Club Mousketeer to multi-platinum-selling artist to cautionary tale and back again, the necessary focus on what brought her down, and the possibility that Britney’s life was barely her own long before the conservatorship was put in place, is a haunting tale worth revisiting.

We’ve heard a lot about Jamie Spears, Britney’s father, since 2008, when he and a lawyer named Andrew Wallet were appointed co-conservators and put in charge of the singer’s person (medical treatment, living arrangements, travel, etc.) and estate (her money and business decisions). Before that, not so much, as mom Lynne Spears (divorced from Jamie since the early ’00s) was Britney’s primary companion in the earliest phase of her career before longtime friend Felicia Culotta took over as her assistant, Lynne needing to return to Kentwood, La., to care for first-grader Jamie Lynn Spears at home. 

Jamie was away a lot for work, and had a history of money trouble, according to reports, including this episode of The New York Times Presents, and he and Britney weren’t extremely close. (Though the scene of Jamie whipping up grits with Velveeta for his daughter in For the Record, MTV’s 2008 documentary on Britney as she pieced her life back together following the trauma of 2007 and early 2008, remains sweet).

“Her mother would do whatever it took, personally and for the family’s sake, for Britney to be a star,” recalls Kim Kaiman, senior marketing director of Jive Records from 1998 until 2004 (aka the rise of Britney), in “Framing Britney Spears.” “Lynne supported Britney. I want to say Lynne because I never talked to her father. The only thing Jamie ever said to me was, ‘My daughter’s gonna be so rich, she’s gonna buy me a boat.’ That’s all I’m gonna say about Jamie.”

No one from the Spears family agreed to go on camera or provide a comment for the show.

Felicia recalls that one Christmas, when Britney was just starting to get famous, the singer withdrew $10,000 in $100 bills and passed them out to people on the street in Kentwood. She just “drove through town wishing people ‘Merry Christmas,'” says Felicia, who explains she was no longer part of Britney’s personal staff after Jamie was put in charge but continued on for awhile as an employee of the tour management company.

New York Times culture writer Wesley Morris interestingly points out that Britney’s star was on the rise (…Baby One More Time dropped Jan. 12, 1999) right when the country had sex on the brain—to an unusual degree, that is—due to the cheating-and-lying-about-it scandal involving Monica Lewinsky that led to President Bill Clinton‘s impeachment.

Fixation on cigars and stained dresses dovetailed with the emergence of super-hot-Britney, which led to controversy even as she sold millions of records and filled arenas, her critics debating whether she was too sexy and perhaps a bad role model for the kids who idolized her. Meanwhile, well-meaning defenders came at it from the other side, objecting to the objectification of Britney, who had just celebrated her 17th birthday when her debut album was released.

Hayley Hill, Britney’s stylist from 1997 until 2001, says that she worked with all the big boy bands at the time, too—and not one of those guys was treated to the sort of scrutiny that Britney was under.

But while others were analyzing her every move and outfit, Britney decided at her still-tender age that she was going to dress however she wanted and do whatever she damn well pleased.

According to Kevin Tancharoen, a backup dancer and tour director for Britney until 2004, anyone who ever thought that the pop star was just going through the motions or otherwise letting other people make creative, personnel or any other decisions pertinent to the business of being Britney Spears was sorely mistaken.

“She was definitely in control of a lot of decisions,” he recalls. “That idea that Britney is a puppet who just gets moved around and told what to do is incredibly inaccurate. When I was involved in all of those years, we would present a lot of ideas and she would have to like them, she would have to approve them. She was very creative. She was the one who knew what she wanted to do, or her people would make [what she wanted] happen for her.”

He concludes, “She was the boss.”

“Pure male revenge fantasy,” is how Tancharoen describes the video featuring a silhouetted woman of Britney-esque size and hair for “Cry Me a River,” Justin Timberlake‘s hit song that fans widely assumed to be an autobiographical brokenhearted lament from a guy whose girl has done him wrong. Kicking over a picture of a beaming pretty blonde in the video did nothing to dispel the notion.

“People treated her like she was the school slut and he was the quarterback,” recalls former MTV VJ Dave Holmes, who notes how Timberlake “weaponized the idea for one of his singles.”

An audio clip of the singer doing a radio interview in which the host asks, mock-solemnly, “Did you f–k Britney Spears, yes or no?” and a gaggle of dudes burst out laughing just goes to show that 2002 wasn’t all that far from 1952.

“What can you say about misogyny?” Wesley Morris observes. “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.”

Seeing that saga re-unfold all at once does make you look at it in a new light, one that illuminates the deck that was stacked against Britney’s agency from the beginning and how unfairly she was treated in a media ecosystem in which man was still the dominant species. Even ABC News’ Diane Sawyer asked her in 2003, referring to the broken heart Timberlake had been parading around while promoting his solo debut Justified: “What did you do?”

“I don’t think I was at all surprised when she and Kevin got engaged,” Felicia says of the whirlwind romance that did shock everyone who didn’t know Britney (so, most people), as well as whoever was holding out hope that she and J.T. would reunite 4-eva.

But having said before that she hoped that one day performing and making music would be a side project once she got married and had kids, she took the first steps toward living the dream when she was 22. Britney swapped vows with Kevin Federline on Sept. 18, 2004 (then married him legally Oct. 6) and in April 2005 she announced her first pregnancy. 

Their second son, Jayden, joined Sean in the family fold on Sept. 12, 2006. Less than two months later, Britney filed for divorce—and so it began.

There’s the horde of paparazzi who follow her wherever she goes, the infamous shots of her driving off with Sean on her lap, the interview with a sockless Matt Lauer as he asks what she has to say about people accusing her of being a “bad mom.”

“That’s America for you,” Britney replies with a glum smirk.

By the end of 2006, into 2007, she was hanging out with known partiers Paris Hilton and Lindsay Lohan and otherwise proving that she still didn’t give a damn about what people were saying about her. In the show, bloggers like Perez Hilton are seen, at the time, boasting that Britney’s good for business, and former paparazzo Daniel Ramos insists that, for awhile, they had a copacetic, mutually beneficial relationship with her.

“She was very friendly, a sweetheart of a girl,” he recalls. “It’s like she needed us and we needed her…it was a great kind of a relationship.”

By the time Britney shows up at a barbershop in February 2007 and, wielding the clippers herself, buzzes all her hair off, you start to feel adequately suffocated, as she must have felt in the days when print magazines were routinely spending $140,000 a week on photographs. 

On Feb. 21, Daniel Ramos’ persistence inspired a frustrated Britney, denied entry to K-Fed’s house just minutes beforehand when she tried to visit their kids, to get out of her car outside a Jiffy Lube and start whacking the paparazzo’s truck with an umbrella.

He admits in hindsight that none of them really thought about the human being on the other side of their cameras back then. In an era when some photos of Britney were selling for as much as $1 million, they simply wanted more shots.

“Working on her for so many years, she never gave a clue or information to us that ‘I don’t appreciate you guys, leave me the eff alone,'” Ramos says. The interviewer off-camera asks, “What about when she said ‘leave me alone’?”

But she would only be talking about that day, the videographer insists. “It wasn’t like ‘leave me alone forever,’ you know what I mean?”

Devoted longtime Family Feud viewers may remember this, but call it a shock to the system now to see “name something that Britney Spears has lost” come up as a category in a clip from a 2008 episode of the gameshow back when it was hosted by John O’Hurley. One contestant’s first guess, “Husband/marriage,” was No. 4. “Her hair” was the top answer.

No. 3? “Her mind.”

Adam Streisand, the lawyer Britney initially tried to hire to represent her in the probate proceedings before she was found unfit to retain her own counsel (he never saw the medical report the judge used to make that decision), recalls the artist accepting that she probably couldn’t avoid the conservatorship from happening, but saying that she did not want her dad to be in charge. She preferred an independent professional.

But, Jamie was appointed co-conservator, along with Andrew Wallet, and the process of bringing Britney back began. By the end of 2008, she had a new album, Circus, and was getting ready to tour.

Less than eight months after being placed on a 5150 hold (and a year after her unfortunate “Gimme More” appearance), she announced the opening of the 2008 MTV Video Music Awards and won Best Female Video, Best Pop Video and Video of the Year for “Piece of Me.”

Many credited the conservatorship and her dad for how great she seemed to be doing.

Instagram changed everything, in that it gave Britney a way to speak directly(ish) to her fans—who were overjoyed to hear from her, and who instantly started trying to decode every post.

Eventually, her avid followers started to wonder what she was really saying with her photo of a mug reading “It’s motherf–king tea time” or the T-shirt that said “We’re all dreamers.” This had to have been Britney’s way of sharing that she has so much to say, and will say it when she can, right? Or has she been asking for help all along?!

Alas, as conspiracy theories tend to do, this one got out of hand, resulting in abuse being hurled at her social media manager, Cassie Petrey, including accusations that she was part of a sinister apparatus at work to control or stifle Britney, as well as at Britney herself. (Which seems antithetical to the cause, but frustrated people react in unpredictable ways.)

Petrey posted Feb. 2: “First and foremost, I absolutely adore the Britney Spears fan base. They are incredible, loyal and passionate about her. I admire them. I know everything they do and say is because they truly love her. Which is why it’s been easy for me to overlook some of the nasty comments that have been thrown my way over the years – because I know deep down it’s all out of love for one of the greatest pop stars of all time.

“However, there are a lot of inaccurate theories out there…and I want to give as much information as I can without violating her privacy or mine.”

Petrey insisted that Britney creates almost all of her own content, even editing the videos herself. But even when she doesn’t hit “share” with her own thumb, she has full discretion over her account, and her team runs everything by her for approval. And for the record, “Britney is ‘not asking for help’ or leaving secret messages in her social media.” Moreover, Petrey added, her work for Britney “does not involve her conservatorship in any way.”

Concern entered overdrive territory when Britney canceled her new Vegas show, Domination, in January 2019, citing her father’s recent health emergency and her desire to just be with her family. Then, she dropped off the grid—or the Insta grid at least, worrying her fans.

In early April, it was confirmed that she had checked into a residential treatment facility for a month to tend to her mental health. She posted that she needed some “me time,” but even then, worried fans were suspicious of her use of a “:)” instead of a more characteristic smile emoji.

Later that month, Tess Barker and Babs Gray, hosts of the Britney’s Grams podcast, played a voicemail they’d received from an anonymous caller. The guy said he was a paralegal who used to work at a law firm that represented Britney and, from what he understood, she had not voluntarily entered that facility, and she supposedly checked in all the way back in mid-January.

In a lengthy message posted April 23, responding to the mass hysteria that included death threats against her team and family, Britney wrote, “Don’t believe everything you read and hear…My situation is unique, but I promise I’m doing what’s best at this moment. You may not know this about me, but I am strong, and stand up for what I want!” In an accompanying video she told her supporters not to worry and promised to be “back very soon.” 

Her longtime manager, Larry Rudolph, also fully denied the claims made in the voice mail, telling the Washington Post that the singer had asked about going to the facility in late March—but the “#FreeBritney” movement had already been born.

Those who call themselves #FreeBritney activists tell the Times that of course it occurred to them that what they’re doing—protesting outside the courthouse during hearings, posting videos on Instagram and TikTok advocating for Britney’s full release from the conservatorship and/or her father’s control—could come off as crazy.

But as Junior Olivas says he told himself when he wasn’t sure if he should show up to protest, “You’re going to get your butt there and help her, just like she helped you.”

Says another activist, Leanne Simmons, “If I’m wrong and one day Britney comes out and tells us we were wrong and to leave her alone, we’ll do just that.”

Until then, they’ll insist that the court #FreeBritney.

The conservatorship, meanwhile, has been extended until at least September. 

But with Britney being more explicit than ever in her court filings about what she wants—namely, that she won’t perform again until her father is no longer in charge of her career—this could be a whole new ballgame come the fall.

Maybe, just maybe, 2021 is going to be the year.

The New York Times Presents’ “Framing Britney Spears” premieres Friday, Feb. 5, at 10 p.m. on FX and will be streaming on FX on Hulu.