Britney Spears timeline: Highs and lows from life and career

Britney Spears smiles broadly with most of her hair pulled back in a black hat

By Nardine SaadStaff Writer

Oct. 26, 2023 6 AM PT

There’s a lot of ground to cover when it comes to understanding Britney Spears and processing her decades-long career, which has been repeatedly eclipsed by her controversial conservatorship and tumultuous personal life.

Now, with Spears contextualizing it all in her new book, “The Woman in Me,” we’re tracking some of her biggest headlines, sprinkled with the backstory she provides in the tell-all.

Spears’ take on her life has been described as a Southern Gothic, feminist horror story, with the “Toxic” singer “often recounting her mistreatment by most of the men in her life.” There are plenty of takeaways to boot. The tome does little to redeem the men who have shaped her life and career. (It’s been a bad week indeed for Jamie Spears, Justin Timberlake and Kevin Federline.)

Here’s a look back at Spears’ most notable career highs and lows, colored by the personal struggles she experienced along the way:

1981 | Born in Mississippi, raised in Louisiana

The pop princess was born on Dec. 2, 1981, in McComb, Miss., to Jamie and Lynne Spears, whom she described in the book as, respectively, a raging alcoholic and a mother “gushing” with blood after giving birth. She has two siblings, older brother Bryan Spears and younger sister Jamie Lynn Spears, of “Zoey 101” and competing-memoir fame.

Spears said her song and dance talents gave her a way to express her voice in a home where it was suppressed: “I worked hard to make things look the way I wanted to,” she writes of being an 8-year-old directing her own imaginary music videos. “Nobody in my town seemed to be doing stuff like that. But I knew I wanted to see it in the world, and I tried to make it so.”

In her autobiography, “Britney Spears’ Heart to Heart,” her mom and co-author, Lynne Spears, explained that the family saw to it that her daughter had dance and music lessons even when they were struggling to pay bills. Spears also played basketball in school and worked at a seafood restaurant cleaning shellfish and serving plates of food “while doing my prissy dancing in my cute little outfits,” the singer wrote.

1993-1995 | ‘The All New Mickey Mouse Club’

After initially failing her first audition for Disney Channel’s “The All New Mickey Mouse Club” because she was too young, Spears eventually joined the star-spawning program. She appeared alongside Ryan Gosling, Christina Aguilera, Nikki De Loach and future beau Justin Timberlake on the show.

1998 | Jive Records deal

Spears was 15 when she signed a deal with Jive Records and felt liberated by her ability to perform without fear, even on her notorious early shopping mall tour. But, as she wrote in the book, the media became adversarial and even grotesque almost as quickly. Spears recalled adult journalists asking her questions about her breasts while simultaneously forcing her to comment on the backlash to her skimpy outfits.

“I was a teenage girl from the South,” she wrote. “I signed my name with a heart. I liked looking cute. Why did everyone treat me, even when I was a teenager, like I was dangerous?”

1999 | ‘...Baby One More Time’

Spears’ breakout bop — accompanied by its sweet-but-rebellious schoolhouse-romp music video — made her a star at 16 and a mainstay of MTV’s “Total Request Live.” Propelled by the hit single, her eponymous debut album spent six weeks at No. 1 on the Billboard 200 chart and nearly two years (103 weeks) total on the chart. That spring, Spears got tongues a-wagging with her navel-baring, busty Rolling Stone cover, but she seemed unstoppable. She launched her first headlining tour that year and won four Billboard Music Awards.

The next year, the song earned Spears two Grammy Award nominations, for new artist and female pop vocal performance, but she lost in both categories — to “Genie in a Bottle” crooner Aguilera and Sarah McLachlan’s “I Will Remember You,” respectively. The album, however, was a multiplatinum hit.

2000 | ‘Oops! ... I Did it Again’

Spears immortalized the full-body red jumpsuit with her music video for her next big hit, “Oops! ... I Did it Again,” the lead single from her sophomore album of the same name. The song earned her two more Grammy nominations but was panned by The Times as having the “same slick soul-pop, metronomic beats and overwrought balladry” as “...Baby One More Time.”

“But, really, who cares what they think?” reviewer Natalie Nichols wrote. “[A]t 18, she hasn’t escaped that awkward stage between childhood and maturity.”

The album sold more than 1 million units in the first week.

2001 | Pop princess status

A half-dozen male and female musical stars perform in the 2001 Super Bowl halftime show

With MTV producing the Super Bowl XXXV halftime show, the network brought big-time talent with “The Kings of Rock and Pop.” The televised spectacle featured Aerosmith and NSYNC, with those top-selling acts alternating songs during the performance. They ultimately closed the gig with “Walk This Way,” featuring Spears, Mary J. Blige and Nelly.

The show, Spears wrote, was “just one of the seemingly endless good things happening for me” in that period of time. She also landed on Forbes’ power lists, in Pepsi commercials and in a movie, “Crossroads.” MTV still counts her slinking performance of “I’m a Slave 4 U” — complete with a white albino python — at the 2001 VMAs among the awards show’s most iconic moments. (Surprisingly, quite a few of those moments involve Spears. But more on that later.)

The singer was ubiquitous on magazine covers, from Cosmo to Rolling Stone, and on talk shows, gracing the studios of “Oprah,” “Rosie” and “The Tonight Show,” as well as “Saturday Night Live.” In 2001, she released her third studio album, “Britney.”

“When I think back on that time, I was truly living the dream, living my dream. My tours took me all over the world,” she wrote, and she was having fun “being 19.” She also said she turned down a role in the movie version of “Chicago,” which she regretted. (She also said she didn’t make the cut for the 2004 film “The Notebook.”)

“I had power back then; I wish I’d used it more thoughtfully,” she said, “been more rebellious.”

That same year, she released her third album, “Britney,” and was touring North America while also dating NSYNC frontman Justin Timberlake — before their pop-star romance came to a screeching halt.

Which brings us to ...

The Justin Timberlake years

Britney Spears and Justin Timberlake in full denim outfits at the 2001 American Music Awards

Spears and the “Bye, Bye, Bye” crooner reunited after working together on “The Mickey Mouse Club.” They started dating in 1999, when she was 17 and he was 18, while both rose to the top of the pop music world. After breaking up in 2002, Spears was blamed for the end of their romance by powerful media figures, including veteran journalist Diane Sawyer, who confronted Spears about Timberlake in a high-profile 2003 interview that brought the “Lucky” singer to tears.

Spears alleged in her memoir that he cheated on her repeatedly, then he broke up with her via a “two-word” text message, went on an infamous PR tour bashing her and wrote songs that painted her as the bad guy in their relationship (Ahem, “Cry Me a River.”) Spears also admits to cheating once on J.T. when she made out with the band’s choreographer, Wade Robson. (Her book is now being considered a blow to Timberlake’s latest comeback.)

“[A]s much as Justin hurt me, there was a huge foundation of love, and when he left me I was devastated,” Spears wrote. “When I say devastated, I mean I could barely speak for months. Whenever anyone asked me about him, all I could do was cry. I don’t know if I was clinically in shock, but it felt that way.”

The biggest bombshell about their relationship was dropped in the week before “The Woman in Me” published: An excerpt revealed that in 2000 Spears had an abortion while dating the musician.

She called her medically induced abortion “one of the most agonizing things I have ever experienced in my life” and said she wouldn’t have done it if she was making the decision without Timberlake, who said “we weren’t ready to have a baby in our lives, that we were way too young.”

Although he hasn’t yet publicly addressed Spears’ allegations, Timberlake publicly apologized to Spears in 2021 after the FX documentary “Framing Britney Spears” for his role in the public backlash against her after their breakup, describing the music industry as male-centric and flawed.

2002 | ‘Crossroads’

Playing a virginal high-school valedictorian in “Crossroads” put Spears off acting. She didn’t enjoy how she disappeared into her character — one of three childhood best friends who embark on a road trip with a guy they just met. It should be noted that the film was bankrolled by a wing of the Zomba Group, whose Jive Records label was home to Spears, the Backstreet Boys and R. Kelly. Zomba was reportedly so eager to team up with MTV Films and the cable channel’s mighty promotional machine that it also put up half of the film’s marketing budget.

“‘Crossroads’ is no ‘Glitter,’” The Times’ review said. “Spears acquits herself as well as anyone might, in a movie as contrived and lazy as this one. She has a natural screen presence and, despite all those irritating vocal tics, makes herself likable. This may come as a shock, but she’s OK.”

With only a $12-million budget, the film could arguably be regarded as a success, making $61.1million at the worldwide box office. And it also gave us this cover, above, of Joan Jett’s “I Love Rock ’n’ Roll.”

2003 | Jason Alexander marriage

Spears revealed in her memoir that her 55-hour marriage to childhood pal Jason Alexander was the result of an alcohol-fueled bender in Las Vegas at age 22 — an impulsive move that deepened the cracks in her public image.

“I was this little girl who had worked so much, and then all of a sudden the schedule was blank for a few days, and so: Hello, alcohol!” she wrote.

The pair got hitched in a wedding chapel at about 5:30 a.m. on a Saturday in January and the next day arranged for an annulment in the presence of several people, including a lawyer. The short-lived newlyweds “took a joke too far by getting married,” her record label said in a statement at the time. (Incidentally, it was Alexander who crashed Spears’ June 2022 nuptials to Sam Asghari.)

2003 | The Madonna-Christina Aguilera kiss

Britney Spears, wearing white, kisses Madonna, wearing black, onstage next to Christina Aguilera

Creating another of the aughts’ iconic pop-culture moments, Madonna locked lips with Spears and Christina Aguilera onstage during the 2003 MTV Video Music Awards while they performed a wedding-themed version of “Like a Virgin.” Madonna handpicked Spears and Aguilera because they were “the best young dancers around.” The provocative performance also paved the way for Spears’ “Me Against the Music,” which featured the Material Girl. The song was the debut single for Spears’ fourth studio album, “In the Zone,” which also featured her signature hit “Toxic.”

2004 | ‘Toxic’ earns a Grammy Award

After six nominations, Spears won her first Grammy — for her dance recording “Toxic.” The singer had already made her Grammy-stage debut in 2000 when she performed a medley of her hits, including “From the Bottom of My Broken Heart” and “… Baby One More Time.”

The Kevin Federline years

Kevin Federline and Britney Spears smile for photographers on an evening out

In 2004, a little more than a year after her quickie wedding to Alexander, Spears began dating backup dancer Kevin Federline. The two met at the Hollywood club Joseph’s Café and Spears said “there was a connection between us” from the moment she saw him. Federline had been a dancer for NSYNC and had a “bad boy” image. Spears claims she didn’t know when she met him that he had already had a toddler and that his ex-girlfriend was eight months pregnant.

“It was beyond a sexual thing. It wasn’t about lust. It was intimate. He would hold me as long as I wanted to be held. Had anyone in my life ever done that before? If so, I couldn’t remember when. And was there anything better?” she wrote. “After what I’d gone through with J, I hadn’t been with someone in a real way in so long.”

They got engaged in July of that year after Spears asked him to marry her. He said no and proposed to her instead. They wed in a surprise ceremony in the San Fernando Valley that September, when she was 22 and he was 26. The following year, they put their union on display by co-starring in five episodes of the short-lived UPN docuseries “Britney & Kevin: Chaotic,” which many critics regarded as career suicide for the star.

2005 | Becoming a mom

Spears and Federline welcomed their first child, son Sean Preston, on Sept. 14, 2005, at Santa Monica UCLA Medical Center. Almost exactly a year later, she gave birth to their second son, Jayden James.

The public scrutiny heightened for the young mother of two children under 2, and she lived under the glare of the media and the legal system as she navigated being a first-time mom. Paparazzi and tabloids scooped up “bad mom” content and her bizarre behavior was caught on tape — her baby fell out of a highchair and suffered scratches, and she was seen driving down Pacific Coast Highway while holding her infant son in her lap.

Spears said she felt “a little depressed” while her kids “seemed so vulnerable out in the world of jockeying paparazzi and tabloids.” Her hormones “were all over the place” and she was “meaner than hell and so bossy. “

“I now know that I was displaying just about every symptom of perinatal depression: sadness, anxiety, fatigue,” she wrote. “Once the babies were born, I added on my confusion and obsession about the babies’ safety, which was ratcheting up the more media attention was on us. Being a new mom is challenging enough without trying to do everything under a microscope.

“With Kevin away so much, no one was around to see me spiral — except every paparazzo in America,” she said.

In that time, she also said that she and Federline grew more estranged while he focused on his music career and newfound solo fame and “it seemed like he wanted to pretend [Spears] didn’t exist.”

“He really thought he was a rapper now. Bless his heart — because he did take it so seriously,” she wrote.

2006 | Divorce

She filed for divorce from Federline in November 2006 after two years of marriage, citing irreconcilable differences. Though she was vilified in the media, she believes that the split helped promote Federline’s album, which was released a week after their divorce announcement.

Erratic behavior soon followed (see “head shaving,” below). Spears found herself frequently in the company of Paris Hilton and in the crosshairs of gossip bloggers who followed her every move.

The Spears-Federline divorce was finalized in 2007, and she lost custody of their two sons that year. Federline was also awarded sole custody of their children when the conservatorship was put into place in 2008. Today, Spears still appears to have some custody of the teen boys, but it’s unclear how much and whether it’s physical, legal or both.

2007 | ‘Gimme More’ (or less) at the MTV VMAs

Singer Britney Spears performs at the 2007 MTV Video Music Awards in 2007 in Las Vegas, Nev.

Spears raised even more eyebrows when she opened the 2007 MTV VMAs with a seemingly dazed, confused, underwear-clad performance of “Gimme More.” The show had been touted as a comeback for a singer who had largely left her professional career behind to focus on her family. Instead, it was a fiasco.

But the September flop in Las Vegas, which included Spears failing to lip-sync portions of the song, launched scores of theories and even more questions about her fitness to return to the stage — let alone parenthood. Meanwhile, her fifth studio album, “Blackout,” was released that October and was critically acclaimed for bringing dubstep and other alt sounds to pop radio. Its lead single, “Piece of Me,” has been characterized as “a sneering indictment of Big Gossip.”

2007-2008 | Head shaving and psychiatric holds

The release of “Blackout,” was sidelined by global headlines about Spears’ personal life, including abruptly shaving her head and subsequently using an umbrella to attack a paparazzo’s SUV. At the time, she argued that her hair extensions had been giving her a headache.

Those incidents and others led to welfare checks and psychiatric holds in early 2008 and laid the groundwork for her family to place her under the controversial conservatorship in California that year.

“Flailing those weeks without my children, I lost it, over and over again. I didn’t even really know how to take care of myself. Because of the divorce, I’d had to move out of the home I loved and was living in a random English-style cottage in Beverly Hills. The paparazzi were circling extra-excitedly now, like sharks when there’s blood in the water. ..,” she wrote. “But if I couldn’t see my sons, I didn’t want to see anybody.”

Shaving her newly dyed brunet locks on Feb. 16, 2007, was her way of “pushing back.” and doing so “felt almost religious” because, she wrote, she had “been eyeballed so much growing up” and had people telling her what they thought of her body for too long.

Days later, when she was again denied entry to Federline’s home to see her sons, she snapped at a paparazzo who just wouldn’t let up.

“I screamed. They liked that — when I reacted. One guy wouldn’t go away until he got what he wanted. He kept smirking, kept asking me the same terrible questions, over and over, trying to get me to react again,” she wrote, describing his “lack of humanity” as he quizzed her about how it felt not being able to see her kids. It was one of the worst moments in her life, she wrote.

“Finally, I snapped. I grabbed the only thing within reach, a green umbrella, and jumped out of the car. I wasn’t going to hit him, because even at my worst, I am not that kind of person. I hit the next closest thing, which was his car. Pathetic, really. An umbrella. You can’t even do any damage with an umbrella. It was a desperate move by a desperate person. “

2008 | Conservatorship begins

A split image of a man in a suit and red tie and a woman in a red dress

Spears’ story is inextricable from her nearly 14-year conservatorship, a legal move by her father Jamie that put him in control of her personal and professional life. The conservatorship was installed against her will in February 2008 and gave him near-total authority of her finances and career. He told her “I’m Britney Spears now,” she wrote in her book.

“If they’d let me live my life, I know I would’ve followed my heart and come out of this the right way and worked it out,” Spears wrote. “Thirteen years went by with me feeling like a shadow of myself.”

In that time, many players were named in legal documents, and Spears had to get two restraining orders against the Svengali-like figure Sam Lutfi, a man/manager/spokesperson who her family said was trying to release private information about the singer. A slew of allegations also flew against her former business manager, Lou Taylor, the founder of Tri Star Sports & Entertainment Group, who allegedly helped set up the conservatorship. Spears also believed it was her mother Lynnes idea to move in that direction as well.

“I think back now on my father and his associates having control over my body and my money for that long and it makes me feel sick … Think of how many male artists gambled all their money away; how many had substance abuse or mental health issues. No one tried to take away their control over their bodies and money. I didn’t deserve what my family did to me,” she wrote.

Still, she performed, notching guest spots on the CBS sitcom “How I Met Your Mother” and leading people to believe that the legal arrangement was to her benefit. But, she wrote, her heart wasn’t in it anymore: “As far as my passion for singing and dancing, it was almost a joke at that point.”

In legal documents released in 2020, Spears was revealed to be worth $59 million, but as her fans and #FreeBritney advocates would argue, she had no control over that sum, which was funding the conservators and lawyers who minded the purse.

2011 | ‘Femme Fatale’

Her seventh studio album, released in March 2011, was her last record at longtime label Jive. The record label shuttered that year and Spears became an RCA Records artist. “Femme Fatale” featured the songs “Hold It Against Me,” “Criminal” and “Till the World Ends” and The Times described it as “plainly one of her best.” Her prior album, 2008’s “Circus,” had yielded “Womanizer,” her first song to reach No. 1 on the Billboard’s Hot 100 chart since “Oops! ... I Did it Again” did in January 1999.

2012 | ‘The X Factor’

Spears returned to TV screens by joining Season 2 of Fox’s talent competition series “The X Factor.” She oversaw a crop of talent alongside Simon Cowell, L.A. Reid and Demi Lovato on the judge’s panel for 28 episodes. But in January 2013, Spears released a statement confirming weeks of speculation that she would not be returning for the show’s third season. Spears’ statement maintained that it wasn’t the producers’ decision, it was hers.

“I had an incredible time doing the show and I love the other judges and I am so proud of my teens, but it’s time for me to get back in the studio. Watching them all do their thing up on that stage every week made me miss performing so much! I can’t wait to get back out there and do what I love most.”

Cowell and the other producers did little to stem reports that they were unhappy with Spears’ lackluster judging performance as the show suffered through double-digit ratings declines despite expectations that Spears’ presence would boost viewership, The Times reported then.

‘Piece of Me’ Las Vegas residency

Spears launched what became a four-year Las Vegas residency at Planet Hollywood Resort & Casino just before New Year’s Eve in 2013. Though her personal life had appeared to stabilize under the conservatorship, the release of her album “Britney Jean” earlier that month showed that her business was still hurting: It opened with the lowest sales of her 15-year career.

But the show — with songs including her early hits and “Work, Bitch,” “Womanizer,” “Circus” and “Till the World Ends” — was so popular that she extended it in 2015 for two more years.

With more than 140 performances under her belt, she closed out the residency on New Year’s Eve in 2017 — the last time she performed live for an audience outside her Instagram feed until now. The show grossed more than $138 million and won the best of Las Vegas award in 2015 and 2017.

2016 | ‘Glory’

Her ninth studio album, “Glory,” came amid her Vegas renaissance. She hasn’t released a new album since.

“Even when the songs are providing her with flimsy messages, Spears on ‘Glory’ sings with real style and attitude, as in ‘Make Me…,’ in which she switches between a breathy murmur in the verse and a euphoric falsetto in the chorus, and ‘What You Need,’ a surprising neo-Motown jam in which she comes far closer to Amy Winehouse than anyone would ever have predicted,” Times pop music critic Mikael Wood wrote.

“As a whole, the performance is a vast improvement over her flat, robotic delivery on ‘Britney Jean’; indeed, it’s the very performed nature of the singing — with Spears’ full battery of signature vocal tics — that makes ‘Glory’ such a good time.”

2017 | Britney’s ‘Gram’

A close-up of the 'Britney' message and picture on a black shirt worn by a man holding a Britney Spears doll

With the singer appearing more and more in the public eye — primarily on Instagram — Tess Barker and Barbara Gray launch a podcast, “Britney’s Gram,” dedicated to humorously dissecting Britney Spears’ enigmatic Instagram account. The podcast ultimately gives rise to the powerful #FreeBritney movement that protested her conservatorship.

2018 | ‘Domination’ axed

Britney Spears points to the sky onstage while singing into a lavalier microphone

Spears put her follow-up residency “Britney: Domination” on hold in late 2018 after her dad’s colon ruptured and he spent a month in the hospital. In January 2019, she abruptly canceled the gig altogether just as it was set to begin. She then checked into a mental health facility.

In a November 2020 court filing, Spears alleged that she was afraid of her father and would reportedly not perform until he no longer had control over her career. In a related hearing, her then-attorney, Samuel D. Ingham III, also blamed the singer’s professional hiatus on her father.

In her book, Spears said she refused to do a dance move for her second residency because she considered it too dangerous. That resistance, she wrote, led to months spent in a $60,000-a-month “luxury” rehab facility in Beverly Hills after her father told her that over-the-counter “energy supplements” had been found in her purse.

“My father said that if I didn’t go, then I’d have to go to court, and I’d be embarrassed. He said, ‘We will make you look like a f— idiot, and trust me, you will not win. It’s better me telling you to go versus a judge in court telling you.’

“I felt like it was a form of blackmail and I was being gaslit,” she wrote. “I honestly felt they were trying to kill me.”

In rehab she was taken off Prozac abruptly, then put on lithium and forced to go through extensive therapy. She spent two months solo and then a month in a building with other patients.

“Three months into my confinement, I started to believe that my little heart, whatever made me Britney, was no longer inside my body anymore.”

2018 | GLAAD’s Vanguard Award

At 36, the pop star stepped out to the Beverly Hilton to accept GLAAD’s Vanguard Award, an honor that is presented to media professionals who have “made a significant difference in promoting equality and acceptance of LGBTQ people.”

“This is so incredibly amazing,” Spears said in a speech about acceptance and inclusion. “I feel like our society has always put such an emphasis on what’s normal. And to be different is always seen as unusual or seen as strange. But to be accepted unconditionally and to be able to express yourself as an individual through art is such a blessing.”

She added, “Events like this, the one we are attending here tonight, show the world that we’re not alone. We can all join hands together here and know that we are all beautiful. And we can lift each other up and show our gifts without hesitation.”

2019 | #FreeBritney gains momentum

Illustration of protesters holding up "Free Britney" signs.

Evolving from a hashtag to a bona-fide movement, the #FreeBritney campaign gained momentum after the “Britney’s ‘Gram” podcasters released a special episode in 2019 featuring a troubling voicemail from someone who claimed to be a former paralegal for a lawyer who worked on Spears’ conservatorship.

The movement was filled with Spears fans as well as disability-rights advocates. Spears said in her book that she first learned of the movement from a kindly nurse in her rehab facility who was willing to show her videos. Now, she credits #FreeBritney with helping her find the courage to challenge and eventually escape the legal arrangement.

2020 | New music

Although Spears hasn’t released an album since 2016, she put out a trio of singles in 2020: “Mood Ring,” Swimming in the Stars” and “Matches,” with the Backstreet Boys.

2021 | ‘Framing Britney Spears’ and ‘Britney vs Spears’

A tectonic shift in the narrative around Spears emerged when a series of documentaries — somewhat fueled by #FreeBritney interest — arrived in 2021. The New York Times-produced “Framing Britney Spears,” which premiered on FX and Hulu, highlighted the invasive media frenzy surrounding the pop star as well as the built-in misogyny that dogged her career. And Netflix queued up its secretive “Project Red” offering later that year, debuting “Britney vs Spears” amid Spears’ pivotal court hearing at the end of September. (TMZ would deliver its take, “TMZ Investigates: Britney Spears: The Price of Freedom,” in 2023.)

Spears didn’t collaborate on either project, but had plenty to say about others telling her story.

2021 | Britney’s explosive court testimony and the end of the conservatorship

Britney Spears fans cheer and raise their hands with a Los Angeles building in the background

Between FX and Netflix’s dueling documentaries, Spears described her conservatorship as “abusive” at an explosive hearing in June, saying, “I’m not happy. I’m so angry it’s insane, and I’m depressed. I cry every day.” She said her father, Jamie Spears, “loved the control he had over me” at times. “He loved it.”

At a momentous Sept. 29 hearing, Judge Brenda J. Penny said that Spears’ situation was “not tenable” and that it reflected “a toxic environment, which requires the immediate suspension of Jamie Spears today.”

On Nov. 21, the L.A. judge ruled to terminate the controversial conservatorship, ending the oversight that had supervised the pop star’s person and estate for nearly 14 years.

Penny restored Spears’ legal rights, effective immediately.

2021 | Music break

Weeks after her conservatorship ended, Spears took to Instagram to explain that she would continue her break from making music and performing, arguing that nobody knew the “awful things” that were done to her and that she was scared of people and the music business.

“They really hurt me!!!!!! Not doing music anymore is my way of saying ‘F— you’ in a sense when it only actually benefits my family by ignoring my real work,” she wrote on Instagram.

2022 | ‘Hold Me Closer’

Spears made a triumphant return to music in August 2022 when Elton John released their splashy duet “Hold Me Closer.” The track featured Spears’ vocals over a mash-up of his early-1970s classic “Tiny Dancer” and the title track from his 1992 album “The One.” Although it was a clear bid to replicate the success of “Cold Heart,” his 2021 collaboration with Dua Lipa, the song debuted in Billboard’s Hot 100 and marked Spears’ highest-charting single since her will.i.am collaboration “Scream and Shout” in 2012. (She and will.i.am released a second collab titled “Mind Your Business” in early 2023.)

2022 | Sam Asghari romance, wedding and divorce

Britney Spears, wearing a silver dress, is sitting at a dinner table with Sam Asghari in a blue velvet suit

After dating for five years, the pair got married in June 2022, about half a year after she undid her conservatorship. But in August, after “The Woman in Me” was finished, Asghari filed for divorce from Spears.

“After six years of love and commitment to each other my wife and I have decided to end our journey together,” Asghari wrote in his Instagram story. “We will hold onto the love and respect we have for each other and I wish her the best always. S— happens,” he continued. “Asking for privacy seems ridiculous so I will just ask for everyone including media to be kind and thoughtful.”

Spears sang a different tune when she broke her silence a day later.

“As everyone knows, Hesam and I are no longer together… 6 years is a long time to be with someone, so I’m a little shocked but… I’m not here to explain why because it’s honestly nobody’s business!!!” the 41-year-old wrote on Instagram.

“But I couldn’t take the pain anymore, honestly!!!,” she added. “I’ve been playing it strong for way too long and my Instagram may seem perfect but it’s far from reality and I think we all know that !!! I would love to show my emotions and tears on how I really feel but some reason I’ve always had to hide my weaknesses !!!

2022 | Miscarriage

Backing up to May 2022, about a month after announcing she was pregnant with her third child, she revealed she‘d had a miscarriage

“It is with our deepest sadness we have to announce that we have lost our miracle baby early in pregnancy,” the pop singer said in an Instagram post signed by Spears and her then-fiancé.

2023 | ‘The Woman in Me’

The pop princess’ memoir, “The Woman in Me,” hit bookshelves Tuesday, culminating the $15-million book deal she had signed with Simon & Schuster in February 2022. The deal was made on the heels of her younger sister’s bombshell tell-all, which Spears said she did not approve of.

Her book, she said, was “a labor of love and all the emotions that come with it,” and reliving everything had been “exciting, heart-wrenching, and emotional, to say the least.” For those reasons, she added, she would read only the introduction for the audio version of the book and leave Oscar winner Michelle Williams to recite the rest.

“Freedom to do what I want to do has given me back my womanhood,” she wrote. “In my forties, I’m trying things for what feels like the first time. ... Now, finally, I’m roaring back to life.”

Times assistant editor Christie D’Zurilla and staff writers Christi Carras, Alexandra del Rosario and Jonah Valdez contributed to this report.