Monday, August 2

Britney Spears’ Ups and Downs Over the Years

The price of fame? Britney Spears’ career and personal life have faced a series of ups and downs over the years.

Spears, who was raised in Kentwood, Louisiana, first showed off her vocal skills on the singing competition Star Search at 10 years old in 1992. Following a stint on The Mickey Mouse Club, she signed a record deal with Jive Records in 1997.

As Spears’ singles, including “…Baby One More Time” and “Oops!… I Did It Again,” climbed the charts, she started a relationship with ‘NSync member Justin Timberlake and the world became even more invested in the pop star. The twosome called it quits in 2002 after three years together amid rumors that Spears was unfaithful.

As the “I’m a Slave 4 U” singer’s popularity continued to grow, so did the attention on her personal life. Spears married her backup dancer Kevin Federline in October 2004 after a whirlwind romance. The twosome later welcomed sons Sean Preston and Jayden James.

In 2007, Spears made headlines for a very public breakdown, which lead her to temporarily lose primary custody of her boys. She was also placed under a legal conservatorship in February 2008, which gave her father, Jamie Spears, control over her finances and her person.

Nearly a decade later, the Grammy winner addressed her battle with mental health during an interview with Marie Claire UK.

“I moved to Los Angeles when I was very young. I was so under scrutiny,” she said in October 2016. “If a hair was out of place, I’d be so anxious. I would get very anxious about so many things.”

Britney added that motherhood made her “so much more accepting” of herself: “That has been a really big thing for me over these last few years.”

After a triumphant comeback and successful Las Vegas residency, Jamie was hospitalized in late 2018 after his colon spontaneously ruptured. As a result, Britney postponed her second Vegas residency in January 2019. More than two months later, she checked herself into a mental health facility.

“The stress has been hard on her,” a source told Us in March 2019. “It’s been a very difficult time.”

Six months later, Jamie temporarily stepped down as Britney’s full-time conservator and Jodi Montgomery, a licensed fiduciary, joined her conservatorship team.

In February 2021, Hulu released an episode of The New York Times Presents titled “Framing Britney Spears,” which renewed public interest in her conservatorship. Four months later, Britney broke her silence about the situation during a remote court hearing.

“I just want my life back,” she said, asking the judge to end the conservatorship. “It’s been 13 years and it’s enough. It’s enough and it makes no sense at all. I’m done.”

Scroll through to revisit Britney’s ups and downs:

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Britney made her debut on The All New Mickey Mouse Club with Christina Aguilera, Ryan Gosling and future boyfriend Justin Timberlake.

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Britney and Timberlake were Hollywood’s hottest couple for nearly four years until the “Lucky” singer reportedly strayed from the relationship. Timberlake went on to write his single ”Cry Me a River,” seemingly about Britney’s infidelity, with a look-alike of the singer starring in the music video. 

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As Britney’s image continued to get sexier, she made headlines for kissing Madonna during the opening of the 2003 MTV Video Music Awards. 

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The “Toxic” singer turned heads in 2004 after she briefly married her childhood friend Jason Alexander in Las Vegas, Nevada. Their marriage was annulled 55 hours later. Britney then started seeing her backup dancer Kevin Federline. The twosome were engaged after three months of dating and documented their relationship on a reality series titled Britney & Kevin: Chaotic. They wed at their home in September 2004. 

Michael Caulfield/WireImage for Sony BMG Music Entertainment

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Less than a year after Britney welcomed son Sean Preston in 2005, she made headlines for driving with the then-infant on her lap rather than in a car seat in February 2006. 

“I was terrified that this time the physically aggressive paparazzi would put both me and my baby in danger,” she said in a statement at the time. “I instinctively took measures to get my baby and me out of harm’s way, but the paparazzi continued to stalk us. … I love my child and would do anything to protect him.”


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Britney and Federline welcomed their second son, Jayden, in September 2006. Three months later, the couple split. The Crossroads actress filed for divorce from the rapper, citing irreconcilable differences, in November 2006. She was often seen partying in Los Angeles that same year, with photos of her out with Paris Hilton and Lindsay Lohan causing a stir in December 2006.  


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Britney hit a breaking point in 2007 when paparazzi captured her shaving her head at a hair salon and subsequently attacking a photographer’s car with an umbrella. A struggle with addiction, an undisclosed mental illness and a bitter custody battle with Federline were reportedly behind her behavior.


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After months of setbacks, Britney was criticized for her attempt at a comeback while performing “Gimme More” at the 2007 VMAs. 

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In early 2008, the “Slumber Party” singer was hospitalized and under evaluation for 72 hours, also known as a 5150 hold. The performer’s father, Jamie, was also named her conservator.

By the end of the year, however, Britney released her sixth studio album, Circus, much to the delight of fans. The singer also appeared to be in better spirits and hit the road for the Circus Tour, which would become her highest-grossing tour.

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Following the release of her seventh and eighth studio albums, Femme Fatale and Britney Jean, respectively, the pop icon announced she had landed a Las Vegas residency. The show, titled Britney: Piece of Me, debuted at Planet Hollywood in December 2013. While it was initially set for two years, the popular show ran for four years, concluding in December 2017.

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Britney and Federline’s relationship was back in the news after he filed for more child support following the “Make Me” songstress’ successful Vegas residency. “[Britney is] angry Kevin is asking for more money because she pays for everything,” a source told Us exclusively at the time. “Those boys are her world. She is an amazing mother.”

The exes reached an agreement in September 2018, with the Crossroads star paying the DJ an additional $15,000 a month. Their original agreement had her giving Federline $20,000 a month.

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Britney announced she was going on an indefinite work hiatus — and putting her second Las Vegas residency titled Domination — on hold after her father, Jamie, fell ill. 

“I am dedicating my focus and energy to care for my family. We have a very special relationship and I want to be with my family at this time just like they have always been there for me,” she said in a statement to Us in January 2019. “Thank you to all my fans for your continued love and support during this time. I apologize for any inconvenience this may have caused and I look forward to the time when I can be back on stage performing for all of you.”

Nearly three months later, multiple sources confirmed to Us that the star checked into a mental health facility amid concerns over Jamie’s illness. 

Britney is at a “wellness center that prioritizes physical, mental and spiritual well-being and Britney will be there for a few weeks,” an insider told Us at the time, noting that her sons “are in the full-time care of their dad, Kevin, for the time being.”

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The former X Factor judge requested to have her father permanently removed as her conservator in August 2020, in favor of having Montgomery become her sole care manager. Her lawyer, Samuel Ingham, told the court that she “strongly opposed” having Jamie return in the role. 

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In June 2021, Britney broke her silence about her 13-year conservatorship during a 20-minute address to the court that was full of bombshell revelations. She said she felt “enslaved” by her father, adding that she had been forced to take lithium against her will, among other things. “You know, fake it till you make it, but now I’m telling you the truth, I’m not happy. I can’t sleep. I’m so angry it’s insane,” she said. “I cry every day.”

The singer also claimed that she wanted to have another child, but her conservators had prevented her from going to the doctor to have her IUD removed. “I have an IUD in my body right now that won’t let me have a baby and my conservators won’t let me go to the doctor to take it out,” she told the court. “I want to be able to get married and have a baby. I was told with the conservatorship I was not able to get married and have a baby.”


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