Everything Britney Spears Says About the Celebrities Mentioned in Her Memoir — from Justin Timberlake to Madonna

The pop icon released her memoir, 'The Woman in Me,' on Tuesday

Britney Spears is reclaiming her voice — and spilling the tea on celebrity encounters she's had over the years — in her new memoir, The Woman in Me.

The hotly anticipated book, which hit shelves on Tuesday, chronicles Spears' journey from child star to chart-topping pop icon, from the highs (music videos, award shows and smash albums) to the lows (her 13-year court-ordered conservatorship, which was terminated in November 2021). Spears also looks back on experiences she had with her peers and mentors over the years.

“It's hard to speak about,” Spears told PEOPLE in an interview, done via email, of recounting her life’s darker moments, including “not getting a moment of peace, the judgments from strangers who don't even know me, having my freedom stripped away from me by my family and the government [and] losing my passion for the things I love.”

But she is ready to take back the narrative.

“It is finally time for me to raise my voice and speak out, and my fans deserve to hear it directly from me,” she said in the interview. “No more conspiracy, no more lies — just me owning my past, present and future.”

Here, PEOPLE breaks down what Spears writes about the celebrities she mentions in The Woman in Me.

Related: Britney Spears Opens Up: 'Finally Free' to Share Her Story in Bombshell Memoir & New Interview — 'No More Lies' (Exclusive)

The Mouseketeers

Spears got her start in showbiz on The Mickey Mouse Club, which she joined at age 11.

"Being in the show was boot camp for the entertainment industry: extensive dance rehearsals, singing lessons, acting classes, time in the recording studio, and school in between. The Mouseketeers quickly split into our own cliques, divided by the dressing rooms that we shared: Christina Aguilera and I were the younger kids, and we shared a dressing room. We looked up to the older kids — Keri Russell, Ryan Gosling, and Tony Lucca, who I thought was so handsome. And I quickly connected with a boy named Justin Timberlake," Spears writes in the book.

The star looks back on the time fondly.

"It was honestly a kid’s dream — unbelievably fun, particularly for a kid like me. But it was also exceptionally hard work: we would run choreography thirty times in a day, trying to get every step perfect," she writes.

And Spears reveals that her budding romance with future-boyfriend Timberlake began on the show's set.

"[Once] at a sleepover, we played Truth or Dare, and someone dared Justin to kiss me," she recalls in the book. "A Janet Jackson song was playing in the background as he leaned in and kissed me."

Max Martin

After Spears signed her recording contract with Jive Records at age 15, she began working with prolific songwriter and music producer Max Martin.

Before they started collaborating, the duo had dinner in New York City to get to know each other.

"As we sat down, a waiter came over and said, 'How may I help you?' Somehow a candle flipped over and sent the whole table up in flames," Spears writes. "Max and I looked at each other in horror. 'We should go now, yeah?' he said. He was magic. And we started working together immediately."

Spears traveled to Martin's native Sweden to work on songs that what would appear on her breakout debut album, ...Baby One More Time, which came out in 1999.

"Max listened to me," Spears says of working with Martin. "When I said I wanted more R&B in my voice, he knew what I meant and he made it happen."

Paula Cole

Shortly after "...Baby One More Time" came out, Spears met singer-songwriter Paula Cole at a party in New York City and says she eventually learned an important lesson.

"When I first heard her voice, I thought she looked completely different than she actually did," Spears writes. "Putting her angelic face to her super-dirty words on 'Feelin’ Love,' her tiny body with the strength of her voice on 'I Don’t Want to Wait,' I realized how powerful it can be when women defy expectations."

Justin Timberlake

After meeting on The Mickey Mouse Club, Spears and Timberlake began officially dating in 1999, when they were 17 and 18, respectively.

"Pretty soon I realized that I was head over heels in love with him — so in love with him it was pathetic," Spears writes of their young love. "We were like magnets."

Spears claims that Timberlake was unfaithful throughout their relationship.

“There were a couple of times during our relationship when I knew Justin had cheated on me. Especially because I was so infatuated and so in love, I let it go, even though the tabloids seemed determined to rub my face in it," she writes. “There were rumors about him with various dancers and groupies. I let it all go, but clearly, he’d slept around. It was one of those things where you know but you just don’t say anything.”

During the relationship, Spears reveals, she became pregnant with the *NSYNC singer's child and went through with a medical abortion because he wanted her to.

Related: Britney Spears Reveals How She and Justin Timberlake Kept Her Abortion a Secret — Even from Her Family

“It was a surprise, but for me, it wasn’t a tragedy. I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I’d anticipated,” Spears writes of the pregnancy in the book. “But Justin definitely wasn’t happy about the pregnancy. He said we weren’t ready to have a baby in our lives, that we were way too young ... 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."

The famous pair broke up in 2002, and the split took a major toll on her, she writes.

"When he left me, I was devastated. When I say devastated, I mean I could barely speak for months," she writes. "Whenever anyone asked me about him, all I could do was cry."

*NSYNC

During the late-'90s and early aughts, Spears rose up the charts alongside Timberlake and his group *NSYNC, as well as the Backstreet Boys.

"His band, NSYNC, was what people back then called 'so pimp.' They were white boys, but they loved hip-hop," Spears writes of Timberlake's boy band. "To me that’s what separated them from the Backstreet Boys, who seemed very consciously to position themselves as a white group. NSYNC hung out with Black artists. Sometimes I thought they tried too hard to fit in."

In the book, Spears also shares a memory of when Timberlake met "Pony" singer Ginuwine on the street in N.Y.C.

"One day J and I were in New York, going to parts of town I’d never been before," she writes. "Walking our way was a guy with a huge, blinged-out medallion. He was flanked by two giant security guards. J got all excited and said, so loud, 'Oh yeah, fo shiz, fo shiz! Ginuwiiiiiine! What’s up, homie?'"

Related: The Biggest Bombshells from Britney Spears' Memoir The Woman in Me

Madonna

After her ...Baby One More Time breakout, Spears began rubbing elbows with pop-star peers — and the Queen of Pop herself.

"I started running into Madonna all over the world," Spears writes. "We’d greet each other as friends."

After Spears and Timberlake split in 2002, Madonna even took Spears under her wing as a mentor, visiting her at home in New York City at the time.

"Madonna’s supreme confidence helped me see a lot about my situation with fresh eyes. I think she probably had some intuitive sense of what I was going through. I needed a little guidance at that time. I was confused about my life. She tried to mentor me," Spears writes of Madonna, who got the young singer into Kaballah at the time.

Spears also writes that the "Ray of Light" singer "did have a good effect on me."

"She told me I should be sure to take time out for my soul, and I tried to do that," Spears writes. "She modeled a type of strength that I needed to see. There were so many different ways to be a woman in the industry: you could get a reputation for being a diva, you could be professional, or you could be 'nice.' I had always tried so hard to please."

To this day, Spears respects Madonna for how she faced industry misogyny and writes: "She had endured so much sexism and bullying from the public and the industry, and had been shamed for her sexuality so many times, but she always overcame it."

The pop divas memorably hit the stage — and locked lips — at the 2003 MTV VMAs.

"Every time we rehearsed it, we did an air kiss," Spears writes of the iconic performance. "About two minutes before the performance, I was sitting on the side of the stage thinking about my biggest performance to date at the VMAs, when I’d pulled off a suit to reveal a sparkly outfit. I thought to myself: I want a moment like that again this year. With the kiss, should I just go for it? ... A lot was made of that kiss."

And the pair went on to collaborate on Spears' 2003 single "Me Against the Music," which Spears recalls as a master class in pop stardom.

"I was in awe of the ways Madonna would not compromise her vision," Spears writes. "It was an important lesson for me, one that would take a long time for me to absorb: she demanded power, and so she got power. She was the center of attention because she made that the condition of her showing up anywhere. She made that life for herself. I hoped I could find ways to do that."

Mariah Carey

On her rise to stardom, Spears once approached Mariah Carey for a photo at an award show, where she knocked on the "We Belong Together" singer's dressing room door.

"She opened it and out poured the most beautiful, otherworldly light. You know how we all have ring lights now? Well, more than twenty years ago, only Mariah Carey knew about ring lights. And no, I can’t just say her first name. To me she is always going to be Mariah Carey," Spears writes.

Carey went on to give Spears a lesson in finding her angles

"I asked if we could take a photo together and tried to take one where we were standing, and she said, 'No! Come stand here, darling. This is my light. This is my side. I want you to stand here so I can get my good side, girl,'" Spears writes. "She kept saying that in her deep, beautiful voice: 'My good side, girl. My good side, girl.' ... I know I won an award that night, but I couldn’t even tell you what it was. The perfect photo with Mariah Carey — that was the real prize."

Steven Tyler

Spears met one of her rock heroes when she performed at the 2001 Super Bowl alongside Aerosmith and *NSYNC.

"I was brought to Steven Tyler’s trailer to meet him right before the show, and his energy was incredible: he was such an idol to me," she writes in the book.

Michael Jackson

Spears took the stage with another music icon in 2001.

"I performed a duet of 'The Way You Make Me Feel' with Michael Jackson to celebrate the thirtieth anniversary of his solo career," Spears writes. "In my heels, I prowled all over that stage. The audience went crazy. At one point it felt like the whole crowd of twenty thousand was singing along with us."

Zoe Saldaña & Taryn Manning

In 2001, Spears filmed her first movie, Crossroads, alongside Zoe Saldaña and Taryn Manning, and she says she had a difficult time on set — but not because of her costars.

"I think I started Method acting — only I didn’t know how to break out of my character. I really became this other person. Some people do Method acting, but they’re usually aware of the fact that they’re doing it. But I didn’t have any separation at all," Spears writes. "I ended up walking differently, carrying myself differently, talking differently. I was someone else for months while I filmed Crossroads. Still to this day, I bet the girls I shot that movie with think, She’s a little … quirky. If they thought that, they were right."

Donatella Versace

After Spears' difficult split from Timberlake, she spent time with designer Donatella Versace in Italy.

"That trip invigorated me — it reminded me that there was still fun to be had in the world. We drank amazing wine and ate amazing food. Donatella was a dynamic host," Spears writes.

The work trip ended up turning into an escape for Spears.

"I was supposed to sing but I really didn’t feel like it, so after I did a little bit of posing, Donatella said we could take it easy," Spears writes. "Donatella is known for her lavish parties, and this one was no exception. I remember seeing Lenny Kravitz there, all these cool people."

Oprah Winfrey

Following the Timberlake breakup, the public became fascinated with the subject of Spears' virginity.

"I’d appreciated it when Oprah told me on her show that my sexuality was no one else’s business, and that when it came to virginity, 'you don’t need a world announcement if you change your mind,'" Spears writes of the talk-show host.

Colin Farrell

In 2002, Spears was single and enjoyed a whirlwind romance with actor Colin Farrell.

Spears and Farrell had "a two-week brawl," she writes in the book. "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.”

In the book, she reveals they began spending time together after she showed up on the set of his action film S.W.A.T. and looks back on when he brought her as his date to the January 2003 premiere of The Recruit.

“As I had before when I’d felt too attached to a man, I tried to convince myself in every way that it was not a big deal, that we were just having fun, that in this case I was vulnerable because I wasn’t over Justin yet,” she writes of how the fling ended.

Natalie Portman

As Spears tried to pick up the pieces following the Timberlake breakup, she writes: "I did try to be social. Natalie Portman — who I’d known since we were little girls in the New York theater circuit — and I even hosted a New Year’s Eve party together."

Christina Aguilera

In the early aughts, Spears believes her contemporaries like Timberlake and Christina Aguilera weren't under as much scrutiny as she.

"While the news about me was often not all that friendly, the entertainment press was full of positive stories about Justin and Christina Aguilera," Spears writes. "Justin was on the cover of Rolling Stone half-naked. Christina was on the cover of Blender, dressed like a madam from the Old West. They were together on the cover of Rolling Stone, him in a black tank top, looking at her with sexy eyes, her looking out at the camera, wearing a lace-up black shirt. In that story, she said she thought Justin and I should get back together, which was just confusing given how negative she’d been elsewhere."

Spears says she felt hurt when people would speak for her.

"Seeing people I’d known so intimately talk about me that way in the press stung. Even if they weren’t trying to be cruel, it felt like they were just pouring salt in the wound," she writes. "Why was it so easy for everyone to forget that I was a human being — vulnerable enough that these headlines could leave a bruise?"

Cher

When Spears was young, she lived in a home previously occupied by more music royalty.

The residence was "a four-story NoHo apartment that Cher used to live in," Spears writes of the apartment, which she lived in while reeling from the Timberlake split. "It had tall ceilings, a terrace with a view of the Empire State Building, and a working fireplace much fancier than the one that had been in the living room of our house in Kentwood."

Robin Williams

The "Toxic singer" had an A-list encounter when she lived in Cher's old building.

"One of the only times I did, a man behind me on the elevator said something that made me laugh; I turned around and it was Robin Williams," she writes.

Diane Sawyer

After the Timberlake split, Spears was interviewed by Diane Sawyer, whose relentless questioning left the pop star in tears.

In the Primetime interview, which aired in November 2003, Sawyer, now 77, grilled Spears on the high-profile split, with a line of questioning inspired by rumors sparked by Timberlake himself that the pop star had cheated on him. At one point during the interview, Sawyer asked Spears about the “spasm of publicity” surrounding her personal life, prompting the pop star to break down in tears and ask the crew to put an end to the chat.

Spears repeatedly declared herself “embarrassed” during the sit-down and was criticized by Sawyer for having “upset a lot of mothers in this country” by shedding her good-girl image via scantily clad magazine covers. (Sawyer began the special by declaring Spears’ abs the “most valuable square inch of real estate in the entertainment universe.”)

"I felt like I had been exploited, set up in front of the whole world," Spears writes of the emotional interview. "That interview was a breaking point for me internally — a switch had been flipped. I felt something dark come over my body. I felt myself turning, almost like a werewolf, into a Bad Person."

Kevin Federline

Spears began dating her second husband Kevin Federline — a former backup dancer for Timberlake — in 2004.

"I held on to him like there was no tomorrow," she writes of their early relationship. "I thought Kevin would give me the stability I was craving — and the freedom, too."

The pair married in 2004, and they welcomed their kids Sean Preston and Jayden James in 2005 and 2006, respectively.

Spears says fame had an effect on Federline.

"One time he came home late and told me he’d been at a party. 'Justin Timberlake was there!' he said. 'Lindsay Lohan was, too!'" Spears writes of how Federline changed. "Kevin was just so enthralled with the fame and the power. Again and again in my life I’ve seen fame and money ruin people, and I saw it happen with Kevin in slow motion."

During their marriage, Federline attempted launching a career as a rapper.

When Federline was preparing to shoot the cover for his album, "He was in the studio all the time," Spears writes. "He really thought he was a rapper now. Bless his heart — because he did take it so seriously."

Spears eventually filed for divorce in 2006, and they finalized it the next year.

"I was young, and I made a lot of mistakes. But I will say this: I wasn’t manipulative. I was just stupid," Spears writes of the split. "That’s one thing Justin and Kevin ruined about me. I used to trust people. But after the breakup with Justin and then my divorce, I never really did trust people again."

Jennifer Lopez

In the book, Spears reveals she admires Jennifer Lopez for the balance she has in her life — and her approach to celebrity.

"Some celebrities handle fame well ... I actually envy the people who know how to make fame work for them, because I hide from it. I get very shy," Spears writes. "For example, Jennifer Lopez, from the beginning, struck me as someone who was very good at being famous — at indulging people’s interest in her but knowing where to draw lines. She always handled herself well. She always carried herself with dignity."

Matt Lauer

By 2006, Spears had become a paparazzi target and tabloid staple. That year, Matt Lauer asked her about the public scrutiny on her being a mother.

"He said that people were asking questions about me, including 'Is Britney a bad mom?' He never said who was asking them. Everyone, apparently," Spears writes. "And he asked me what I thought it would take for the paparazzi to leave me alone. I wished he’d ask them — so whatever it was, I could do exactly that."

Olivia Newton-John

When Spears and Federline were still together, they had some other famous neighbors in L.A.

"My home was a safe haven. Our relationship was in trouble, but Kevin and I had built an incredible house in Los Angeles, right beside Mel Gibson’s house," She writes. "Sandy from Grease lived nearby, too. I’d see her and call out, 'Hi, Olivia Newton-John! How are you, Olivia Newton-John?' It was a dream house."

Jimmy Kimmel

After Spears had filed for divorce from Federline, she presented Mary J. Blige with an award at the American Music Awards in 2006, where host Jimmy Kimmel took aim at her ex.

"[Hed] delivered a monologue and skit about Kevin, who he called 'the world’s first-ever no-hit wonder.' They sealed a stand-in into a crate and put it on a truck and dumped it into the ocean. But this was the father of my two infant sons. I found the violence toward him unsettling," Spears writes. "I hadn’t known that was going to happen and it caught me completely off guard ... I had been blindsided and didn’t like it. I also didn’t think that in the midst of a custody battle, having my ex-husband treated that way would be of any benefit to me."

Paris Hilton

When Spears was struggling with postpartum depression after her divorce, Paris Hilton became a source of support and was "kindest to me when I really needed kindness."

"So much of America dismissed her as a party girl, but I found her elegant — the way she posed on the red carpet and always had an arched eyebrow when anyone was mean about her," Spears writes. "She saw that I had babies and that I was suffering from the breakup, and I think she felt sorry for me. She came over to my house, and she helped me out so much. She was just so sweet to me."

In the book, Spears also looks back on her infamous night out with Hilton and Lindsay Lohan.

“It was never as wild as the press made it out to be,” she writes of their now-iconic outings.

Sarah Silverman

Following a public breakdown, Spears returned to the MTV VMAs in 2007 to perform her cult classic "Gimme More." At the show, Sarah Silverman took a shot at the pop star.

"She said that at the age of twenty-five I’d done everything worthwhile in my life I’d ever do. She called my two babies 'the most adorable mistakes you’ll ever see,'" Spears writes. "I didn’t hear that until later, though. At the time I was backstage sobbing hysterically."

Ryan Seacrest

Spears' acclaimed album Blackout came out in 2007 during a difficult time for Spears. She only did one interview to promote the project: a live radio interview with Ryan Seacrest.

"In the interview, which was supposed to be about the record, Ryan Seacrest asked me questions like 'How do you respond to those who criticize you as a mom?' and 'Do you feel like you’re doing everything you can for your kids?' and 'How often will you see them?'" Spears writes. "It felt like that was the only thing people wanted to talk about: whether or not I was a fit mother. Not about how I’d made such a strong album while holding two babies on my hips and being pursued by dozens of dangerous men all day every day."

Julia Michaels & Justin Tranter

During her 13-year conservatorship, while her father was in control of her financial and personal affairs, Spears says she lost her creative spark. But writing and recording her 2016 album Glory with "Issues" singer Julia Michaels and go-to songwriter Justin Tranter reinvigorated her.

"We’d sit and write everything together. I had a passion about it. It was the one thing in the thirteen years of the conservatorship that I really put my heart into," Spears writes. "I worked hard on the songs, which gave me confidence. You know when you’re good at something and can feel it? You start doing something and think, I got this? Writing that album gave me my confidence back."

And the album has sentimental meaning to Spears because her sons helped her name it.

"My kids are really smart about music. 'Just name it Glory,' Sean Preston said. So I did," she writes. "Seeing the kids so proud of that album meant a lot to me — I thought, I’m so proud of this, too! It was a feeling I hadn’t had in a long time."

Amy Schumer, Kevin Hart, Sebastian Maniscalco & Jo Koy

Under the conservatorship, Spears says she found comfort — and inspiration —following comedians on Instagram.

"I ... found myself laughing more — transported by comedians like Amy Schumer, Kevin Hart, Sebastian Maniscalco, and Jo Koy," she writes. "I developed such respect for their wit and their cleverness, how they use language to get under people’s skin and to make them laugh. That’s a gift. Hearing them use their voices — being so distinctively themselves — reminded me that that was something I could do, too, when I made videos on social media or even just in a caption. Humor made it possible for me not to get consumed by bitterness."

Elton John

Last year, Spears teamed up with Elton John on the duet "Hold Me Closer," which became her first Top 10 single on the Billboard Hot 100 chart in 11 years after its August 2022 release.

"For some time I hadn’t been thinking about recording. I changed my mind about that when I got invited to record a song with an artist I’ve admired my entire life: Sir Elton John. He’s one of my all-time favorite performers," Spears writes. "I’d met him at an Oscars party about a decade ago and we got along so well. And now here he was reaching out with the sweetest video message, asking if I would be interested in collaborating. I was so honored."

Spears sees similarities between her journey and John's.

"Like me, Elton John has been through so much, so publicly. It’s given him incredible compassion," she writes. "To make the collaboration even more meaningful: as a child, I listened to 'Tiny Dancer' in the car in Louisiana as I rode to and from my dance and gymnastics classes. … Recording 'Hold Me Closer' and putting it out into the world was a fantastic experience. It didn’t feel good. It felt great."

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