Britney Spears’ stunning transformation through the years– as she's finally free of conservatorship & moves on with life
BRITNEY Spears became the reigning Princess of Pop when she made her explosive solo debut in 1998.
Since then, she has been idolized as a global superstar with six No. 1 albums and a successful Las Vegas residency.
Unfortunately, her life has also been riddled with personal woes, like several failed marriages and engagements, mental health struggles, and her infamous conservatorship.
Let’s take a look at Britney Spears’ beautiful transformation through the years – from adored teen starlet to troubled superstar to conservator-free bride.
MEET BRITNEY
AGE: 11
Britney got her first break as an entertainer when she landed a job performing alongside fellow future A-listers Christina Aguilera, Ryan Gosling, and Justin Timberlake on The All-New Mickey Mouse Club at age 11.
“I made so many wonderful friends from around the world, you know?
“And it was really sad when we had to leave because we were with these people for like two years day after day and then all of a sudden you can’t be with them anymore,” a teenage Britney recalled in an interview with Disney when re-visiting the set at MGM Studios.
Two years is all Britney got with her castmates, as the Mickey Mouse Club stopped production in 1995.
BRITNEY SKYROCKETS TO FAME
Age: 16
Even though her time with Disney ended, Britney was determined to live her dream as an entertainer and made that dream come true in 1997 when she signed with Jive Records.
In 1998, the 16-year-old rising star released her first and arguably most iconic single, …Baby One More Time.
The following year, her debut album of the same name, on which she got to work with some of the world’s top producers who previously collaborated with Whitney Houston, the Backstreet Boys, and NSYNC, dropped.
Her life was forever changed.
The album rose to the top of the Billboard charts and made Britney Spears a household name.
Although she became adored by millions, Britney also received some harsh criticism and was accused of dressing too promiscuously for a high-school-aged girl, as the outfit she wore in her …Baby One More Time music video was a sexier take on Catholic school uniform paired with her dirty blonde hair styled in braids.
She didn’t let the hate bother her too much, though.
In an interview with Entertainment Weekly in 2001, she said: "There are so many other teenagers out there that dress more provocatively than I do and no one says anything about them.”
She also said she was against the idea of herself as being a sex symbol.
BRITNEY TURNS HEADS
AGE: 19
An interest in Britney’s personal life came with her instant success, and fans adored her relationship with former Mickey Mouse Club star, Justin Timberlake.
The matching denim outfits they rocked at the 2001 American Music Awards forever changed what it means to have a red carpet moment and is a staple couple’s costume to this day.
Britney wore a tight strapless dress with her frosted blonde hair falling just below her shoulders, while Justin donned a matching denim suit and cowboy hat.
Unfortunately, their relationship seemed to end on a sour note, as Justin depicted a Britney lookalike cheating on him in his 2002 Cry Me a River music video.
The denim moment isn’t the only head-turning look Britney donned in 2001.
She also made headlines when she performed at the 2001 Video Music Awards with a python around her neck.
Once again, Britney proved she knows how to steal the show two years later when she returned to the VMA stage and locked lips with Madonna.
BRITNEY BECOMES A WIFE, TWICE
AGE: 23
Britney shocked the world when she got married in 2004 not once but twice.
Her first marriage was to childhood friend Jason Alexander, and they wed at the Little White Wedding Chapel in Las Vegas.
In a televised interview with Access Hollywood (via Today), Britney said the sudden wedding “was just crazy.”
"And we were just looking at each other and said, 'Let’s do something wild, crazy. Let’s go get married, just for the hell of it,”’ she recalled.
The marriage was annulled 55 hours later.
Britney then met backup dancer Kevin Federline at a nightclub in Los Angeles and quickly fell in love.
They got engaged after a few months of dating and were officially husband and wife on October 6 of that year.
“It wasn’t the big, traditional wedding.
"It was cool and it was nice and special and small, and I liked it a lot,” the singer gushed in footage from a five-episode 2005 docu-series, Britney and Kevin: Chaotic (via Us Weekly).
BRITNEY HAS A BABY
AGE: 24
Kevin, who was already a father of two, and Britney started their family in 2005 by welcoming their first son, Sean Preston Federline nearly a year after they tied the knot.
She showed off her pregnancy glow and baby bump while walking hand-in-hand with Kevin on the Hollywood Walk of Fame at the Charlie and the Chocolate Factory premiere.
She wore a shirt that claimed her baby was the golden ticket.
Their second son, Jayden James Federline, was born the following year.
TOUGH TIMES
AGE: 26
The years following the birth of her children were not easy for Britney.
First, she and Kevin divorced in 2006 due to “irreconcilable differences.”
Reflecting on the marriage in a 2008 MTV documentary, she admitted she didn’t get married for the right reasons.
"Instead of following my heart and, like, doing something that made me really happy.
"I just did it because … for just, like, the idea of everything," she noted.
The divorce was finalized in 2007, which proved to be a trying year for the superstar.
Britney famously suffered a public breakdown when she defiantly shaved her brown locks after a hairdresser in California refused to do so herself.
Paparazzi, who followed Britney around day and night, caught every moment of the ordeal.
They also documented Britney when she smashed a paparazzo’s car with an umbrella days later.
In the 2019 documentary, Britney Spears – Breaking Point, tattooist Emily Wynee-Hughes opened up about the conversation she had with Britney after she shaved her head.
"I noticed her hair was gone.
"I remember asking her: 'Why did you shave your head?' And her answer was a bit weird," Emily recalled.
"It was, you know, 'I just don't want anybody, anybody touching my head.
"'I don't want anyone touching my hair. I'm sick of people touching my hair.'"
She added that Britney’s team, who was present with her, didn't seem to be alarmed by what had happened.
"It just seemed like everybody was waiting for the crash to happen," Emily stated.
BRITNEY’S PARENTS TAKE CONTROL
AGE: 27
Britney wowed her fans when she dyed her signature blonde locks brown in 2008, but that was far from the biggest change for the Womanizer singer.
That year, she was admitted to the psych ward at UCLA Medical Center where her mental health was evaluated.
She was then placed under the conservatorship of her father, Jamie Spears, who was given full control of the singer’s finances, business arrangements, and career.
Britney also lost custody of her children.
BRITNEY FINDS LOVE AGAIN
AGE: 30
Britney, who continued her singing career as normal under the conservatorship, found love again with her former agent, Jason Trawick.
They got engaged in December 2011 after more than a year of dating, and Britney appeared to be beaming.
The couple went their separate ways the following year.
BRITNEY ON FIRE
AGE: 35
Despite suffering personal woes in the spotlight, Britney continued releasing music and performing for years after entering her conservatorship.
She released a documentary in 2008 titled For the Record, in which she opened up about some of her personal matters.
"I wanted to make this film because I started to feel like I wasn't being seen in the light that I wanted to be seen in," she said in a statement, per Rolling Stone.
"This is an opportunity to set the record straight and talk about what I've been through and where I'm headed."
Britney also embarked on a tour to support her sixth studio album, Circus, and participated in a Las Vegas Residency from 2015 to 2017.
The residency was extended in 2016 for an additional two years, but got cut short when her father underwent health issues.
However, she embarked on her ninth tour, Britney: Live in Concert, between 2017 and 2018.
Her final stop on the tour would be the last time anyone saw her live, as she later announced she would be taking a break.
RED FLAGS FOR BRITNEY
AGE: 39
Red flags started rising at the end of the 2010s when fans caught wind of some concerning actions being taken in Britney’s conservatorship, such as a pay increase for her conservator.
In 2020, fans rallied in support of Britney when she requested that her father, who temporarily stepped down from heading her conservatorship in 2019 due to health concerns, be completely replaced.
This motion was denied, which drove Britney’s loyal supporters to be even more interested in what actually went down behind closed doors.
In a statement in court (via AP News), Britney's lawyer, Samuel D. Ingham III, said: "My client has informed me that she is afraid of her father.
"She will not perform again if her father is in charge of her career."
That statement only confirmed what fans were afraid of: Britney was being treated unfairly by her family.
Fans showed even more concern when her Instagram posts became a bit bizarre, with many coming to the conclusion that Britney was trying to send messages for help to her fans.
For instance, fans told her to wear yellow in her next video if she was in distress – and she did.
BRITNEY IS FREE
AGE: 40
After a tense legal battle with her family and conservatorship, and growing pressure from the public to rid Britney of her conservatorship, she was freed.
Britney’s conservatorship was terminated on November 12.
Now, Britney seems to be happy and ready to move on with her life.
She is engaged to longtime boyfriend Sam Asghari and she often shows their adventures together on Instagram.
Right before the end of her conservatorship, Britney gave an update on her career and blasted her family on the platform.
"Lord have mercy on my family’s souls if I ever do an interview !!!
"In the meantime … I’m staying clear of the business which is all I’ve ever known my whole life … which is why this is so very confusing for me !!! "
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