The Most Surprising Confessions In Britney Spears' Memoir The Woman In Me

Few pop stars have known the kind of tumult that Britney Spears has. Notwithstanding her crowning as the undefeated "Princess of Pop" through the 1990s and 2000s, her personal life remained in flux under the stronghold of factors that included a domineering conservatorship, tabloid attention, very public breakups, and ceaseless sexist commentary. As Samantha Stark, director of the acclaimed 2021 documentary "Framing Britney Spears," put it to Vox, "We were just so mean to young women back then!" The termination of Spears' conservatorship, which had controlled major parts of her life, marked a turning point that finally enabled Spears to tell her story, in her words. And the "Gimme More" singer made extensive use of that power. 

Her memoir, "The Woman in Me," which is scheduled to hit book stands on October 24, 2023, will give the world an in-depth look at Spears' side of the narratives that have long been appropriated by third parties. From her infamous head-shaving incident in 2007 to her complicated moments with ex-boyfriend Justin Timberlake and her fabled indulgence in substances, Spears touches upon many major events that dominated the pop culture conversation around her at the height of her fame. 

Excerpts of the autobiography — an audiobook of which will be narrated by Hollywood star Michelle Williams — have generated widespread anticipation among audiences who have already propelled it to bestseller status. Before its much-awaited upcoming release, preview the most surprising confessions in Britney Spears' memoir "The Woman In Me." 

Britney Spears' conservatorship, and her freedom from it, has been among the most talked-about aspects of the pop star's life in recent years. Her memoir "The Woman in Me" sheds brighter light on her time under the charge of her father, Jamie Spears, and the emotional impact it left on her. "The conservatorship stripped me of my womanhood, made me into a child. I became more of an entity than a person onstage," she writes, according to an excerpt in People. 

Describing herself as "a sort of child-robot" commanded by adults around her, the Grammy winner painfully details how the conservatorship altered her relationship with her art: "I had always felt music in my bones and my blood; they stole that from me. ... It was death to my creativity as an artist." Britney's premature start in showbiz had always allowed other people to wield proxy power over her life, a trend that continued into her adulthood under the restrictive conservatorship. 

While Britney Spears' 13-year ordeal only ended in 2021, The New York Times reported that the music icon had attempted to terminate the "oppressive and controlling tool" that directed her life. The dissolution of the conservatorship by a Los Angeles court gave Britney a free hand to opine on her experience. As she said, "It is finally time for me to raise my voice and speak out. ... No more conspiracy, no more lies — just me owning my past, present and future." 

Britney Spears' relationship with her mother, and alcohol, has been characterized by longtime complications. The two circumstances seemed to converge when Britney was still in school and apparently indulged in underage drinking with Lynne Spears, her new memoir reveals. "For fun, starting when I was in eighth grade, my mom and I would make the two-hour drive from Kentwood to Biloxi, Mississippi, and while we were there, we would drink daiquiris," she writes, according to People. Britney doesn't write about this custom she shared with her mom remorsefully, emphasizing instead how she loved being able to enjoy what the mother-daughter duo called "toddies" together. She was in eighth grade at the time. "We became happier, more alive and adventurous," she adds.

This is not the first time that the early beginnings of Britney's alcohol use has been alluded to. During what was a volatile period between the mother-daughter pair, Lynne made allegations about her daughter's life in her 2008 memoir "Through the Storm: A Real Story of Fame and Family in a Tabloid World" that rocked tabloid headlines. Along with a string of other explosive claims, Britney's mother wrote that the singer's alcohol use began as young as 13 during her time on "The Mickey Mouse Club," UK paper The Sun reported (via Fox News). Following the end of her conservatorship in 2021, there seemed to be a semblance of reconciliation between Britney and her mother. 

Britney Spears and Justin Timberlake's romance was the stuff of Y2K dreams. They were childhood sweethearts, having connected on the sets of the '90s revival of "The Mickey Mouse Club." Sparks flew from the get-go, as Spears reveals in "The Woman in Me" (via People). A sleepover kiss, which was soundtracked by a Janet Jackson song, marked the start of what would turn out to be a protracted, bumpy relationship between the two. 

Spears and Timberlake started going out in 1999, capturing the fantasies of millennial youth and pop culture pundits enamored by the romance illustrated in their kitschy coordinated outfits and public declarations of love. By 2002, the curtain fell on what remains one of the most memorable pairings in music history. "I mean, I really thought that I was gonna be with him for the rest of my life," Spears told ABC News' Diane Sawyer in her now-infamous 2003 interview.

In her book, Spears goes a step further to reveal that she had even become pregnant during her relationship with Timberlake but, at her ex-partner's insistence, decided to undergo an abortion. An excerpt published by People reads, "He said we weren't ready to have a baby in our lives, that we were way too young." Acknowledging it as one of her most difficult moments, Spears continues, "If it had been left up to me alone, I never would have done it." 

To say that Justin Timberlake and Britney Spears' breakup in 2002 was messy would be an understatement. The parting of the young couple, once the image of storybook millennial romance, left in its wake a litter of broadsides that hinted at infidelity affecting their relationship. The general consensus at the time was that Spears had been unfaithful to Timberlake — a suggestion expedited by his songs "Cry Me a River" and "Horrible Woman." In addition, he laid bare intimate details about their sex lives, attracting further jeering against Spears. "In the news media, I was described as a harlot who'd broken the heart of America's golden boy," Spears writes in her book, referring to the flood of attacks that came her way over allegations that she cheated (via Time). 

In the thick of the infidelity narrative that hounded her, Spears appeared on ABC News with Diane Sawyer and offered a vague statement on it: "I'm not technically saying he's wrong, but I'm not technically saying he's right either." Two decades on, her memoir confirms the longtime rumor that she briefly got together with dancer Wade Robson during her time with Timberlake. "We were out one night and we went to a Spanish bar. We danced and danced. I made out with him that night," Spears writes, according to an excerpt in The Sun. Her confession, however, doesn't come without a counter-claim against Timberlake, who apparently cheated on her on more than one occasion. 

One of the most shocking moments in Britney Spears' immediate post-Justin Timberlake era was her interview with legendary journalist Diane Sawyer in 2003. Still fresh from her breakup with the *NSYNC member — who made little effort to rein in the bitterness he felt and spilled sensitive details about the couple's relationship in the press — Spears was at the receiving end of widespread criticism and sexist vilification in the public domain. Sawyer, a senior journalist, added to the noise. 

She took a notoriously disparaging tone when Spears appeared on her ABC News segment, asking the singer, "You did something that caused him so much pain, so much suffering. What did you do?" Her breakup with Timberlake wasn't the only focus point, unfortunately. From needling Spears over her sex life to slut-shaming her over her skin-baring photos, nothing seemed to have been off-limits for Sawyer, who earned much criticism later for her interview that left Spears in tears. 

"I felt like I had been exploited, set up in front of the whole world," Spears writes about the pivotal event in her memoir, calling it a "breaking point," The New York Times reported. After her conservatorship ended in 2021, Spears had weighed in on her chat with Sawyer, saying she had been forced to make that appearance. "What was with the 'You're in the wrong' approach?? Geeze ... and making me cry?" she questioned in a now-deleted Instagram post (via Harper's Bazaar). 

Remember the famous shaved head splashed across tabloid covers in 2007? Britney Spears opens up about that tragically definitive incident in her life and the details behind it in her upcoming memoir, "The Woman in Me." At the time of what was widely called a "meltdown" — characterized by the loss of Spears' iconic gold locks, rehab stints, and driving defaults — the "Toxic" hitmaker was in the midst of acrimonious divorce proceedings with her ex-husband Kevin Federline, with whom she shares two children. Conjecture, criticism, and commentary girdled her, drawing unsolicited inferences about her life. Take stock of this opinion from ABC News: "The one-time pop princess is acting out and in dire need of help." 

Giving the public an insight into her side of the story, Spears writes that it was her lifelong exposure to comments over her appearance that pushed her over the edge. "Shaving my head and acting out were my ways of pushing back," an excerpt published by People reads. Her contentious conservatorship, which clamped down on her autonomy by handing over the reins of her life to her father, maneuvered her toward keeping a favorable public image. "I had to grow my hair out and get back into shape." But her troubles weren't over. 2008 didn't start off on the right note for Spears, who lost custody of her sons to Federline, had to face accusations of drug abuse, and was eventually placed under a conservatorship. 

There was a lot that strained Britney Spears' relationship with her father, Jamie Spears, not least the conservatorship that gave him unbridled control over his daughter's life. The unhealthy dynamic wasn't just restricted to Jamie's hold over Britney's resources but her physical self, too. The pop princess, in her tell-all memoir, reveals that her father was disposed to making comments about her physicality, among other things — a practice that negatively affected her. 

"If I thought getting criticized about my body in the press was bad, it hurt even more from my own father. He repeatedly told me I looked fat and that I was going to have to do something about it," she writes, according to People. She continued about the "soul-crushing state" she was left in during her youth, owing to her father constantly reiterating her supposed inadequacy. In retrospect, the thought of Jamie controlling her life made her feel sick. 

Jamie's troubling comments body-shaming his daughter have also been publicized previously by a friend of the Spears family. Recalling Jamie's words for The New Yorker in 2021, Jacqueline Butcher repeated, "You're fat. Daddy's gonna get you on a diet and a trainer, and you're gonna get back in shape." At the height of the media scrutiny surrounding her in the 2000s, Britney's appearance was often a subject of discussion in the press, which didn't spare her even as she went through a divorce and custody battle in 2007.

Britney Spears' career is a glittering tapestry of iconic moments, one of them being her show-stopping performance at the 2001 MTV Video Music Awards. The bit is etched in pop culture history on account of Spears flawlessly delivering the fan favorite number "I'm a Slave 4 U," as a wild serpentine beast casually lounged on her shoulders. For millennial audiences, it was an electrifying spectacle. For Spears, not so much. 

The singer was panic-stricken through her performance for fear of being attacked by the python. "All I knew was to look down, because I felt if I looked up and caught its eye, it would kill me," she writes in her memoir, per People. She recalls a particularly hellish moment during the show when the python came up to her face and did what pythons inherently do: hissed.

"I was thinking, Are you f***ing serious right now? The f***ing goddamn snake's tongue is flicking out at me," she writes. Needless to say, she was happy to get rid of her hissing prop when the time called for it. While her book description draws one to relive the terror of the event, Spears' take on it hasn't been all fatalistic. Back in September 2023, the singer took to social media to refer to the VMAs show as one of her favorites. Oh, and did we mention? The same performance also had her caged with a tiger. What an icon.

Her early encounter with fame made Britney Spears a steady target of unfair treatment, a practice that continued well into her adulthood for years on end. The former child star recounts in her tell-all memoir an uncomfortable experience she had with iconic television host Ed McMahon when she was only 10. In an incident that was also highlighted in the 2021 documentary "Framing Britney Spears," the pop icon shared the stage in 1992 with McMahon on his show "Star Search," where she belted out a rendition of the Judds' "Love Can Build A Bridge." 

Her performance was followed by a particularly iffy line of questioning from McMahon, who asked the budding singer if she had a boyfriend. She answered in the negative and underlined, in all her girlhood innocence, that boys are mean. "You mean all boys are mean? I'm not mean, how about me?" McMahon prodded, leading the visibly hesitant young Spears to appease the older presenter with a stopgap answer. Spears writes in her memoir that she "kept it together" for a bit, "But then I burst into tears" after leaving the stage (via The New York Times).

Retrospective commentary makes no bones about the unbridled culture of sexism early aughts stars like Spears were subjected to – a fact driven home by her documentary, and now her book. "Everyone kept making strange comments about my breasts wanting to know whether or not I'd had plastic surgery," Spears writes. 

Britney Spears' primary identity is that of a pop star, which often leads people to overlook her short-lived albeit existent acting career. Simultaneous to Spears' booming millennial celebrity as a singer was her brief indulgence in big screen features, starting with the 2001 ensemble comedy "Longshot." While the Lou Pearlman-focused film hardly mined Spears' latent acting skills, her next venture attempted to — but ironically ended up killing her interest in the field altogether. Shonda Rhimes' "Crossroads" was a teen flick starring names like Zoe Saldana and Kim Cattrall beside Spears. 

The 2002 dramedy was critically panned and didn't leave a lasting impact, except on Spears. The singing sensation reveals in her memoir that the film proved to be difficult since she got too into the skin of her character. "I think I started Method acting — only I didn't know how to break out of my character. I really became this other person," she wrote in her memoir (via People). "That was pretty much the beginning and end of my acting career, and I was relieved." 

Her detachment from what she calls an "occupational hazard" also cost her the lead part in the beloved 2004 romance "The Notebook," for which she was apparently considered against Rachel McAdams. Starring in what could have been a career-making role would also have reconnected Spears with her childhood buddy Ryan Gosling, alongside whom she appeared on "The Mickey Mouse Club." But, as she mentions, she didn't regret passing it up.

Much has been said about Britney Spears' substance use. "The Woman in Me" presents the singer's own version of events as they transpired during her fever dream days as a pop sensation. Her association with Y2K "It girl" cliques headlined by regular revelers like Paris Hilton built a narrative around her supposedly untamed, glamorous life but, as Britney writes in her book (via The New York Times), "It was never as wild as the press made it out to be." She maintains that the myth of her drinking problem — exaggerated by the media that reported on her Alcoholics Anonymous sessions — was overplayed. 

As for drugs, Britney admittedly favored Adderall that "gave [her] a few hours of feeling less depressed." The extent of Britney's substance dependence has long been debated, especially in light of insinuations from people acquainted with her life. One of them, her mother, Lynne Spears, wrote in her own memoir that the singer got involved with drugs in her teens; her messy custody battle with ex-husband Kevin Federline added fuel to her alleged drug chronicles, inviting discourse from ex-staffers and ex-boyfriends. 

Britney, meanwhile, has said her substance use was less recreational, more forced. Testifying in court during her conservatorship case, she claimed she was put on lithium, a powerful drug used in the treatment of mental disorders. According to The Independent, she said, "I felt drunk, I couldn't even have a conversation with my mom or dad about anything."