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News

Britney Spears Through the Years

Britney Spears handout for I Am Britney Jean documentary in 2013
Michelangelo Di Battista/Sony/RCA via Getty Images
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Britney Spears Through the Years

By Meredith B. Kile and Emily Krauser

11:52 AM PDT, June 27, 2024

With a career spanning over two decades and 10 studio albums, America has followed pop princess Britney Spears through good times and bad, from "...Baby One More Time" to "Work B**ch."

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Mouseketeers

Disney Channel
Britney made her showbiz debut on Disney Channel's The Mickey Mouse Club, alongside future stars like Christina Aguilera, Ryan Gosling, and future boyfriend Justin Timberlake.

Baby One More Time

Getty Images
Rocking pink and pigtails, the teen pop star performed her debut hit single "Baby One More Time" at Universal Studios, California in July 1999.

Total Request Live

Getty Images
Remember TRL? Remember CDs?! Brit Brit stopped by the popular MTV countdown show in May 2000 with a stack of her new album Oops...I Did It Again.

VMA Striptease

Getty Images
Britney shocked the world and shed her wholesome "girl next door" image at the 2000 Video Music Awards, stripping off a black suit to reveal a sequin-studded flesh-colored bodysuit. The show kicked's off Spears' tradition of memorable VMA performances.

Billboard Beauty

Getty Images
A fashion icon since she came on the scene, Brit Brit's made some questionable choices over the years, including this ensemble she wore to the 2000 Billboard Music Awards, where she took home awards for "Albums Artist of the Year" and "Biggest One Week Album Sales."

Super Bowl Superstars

Getty Images
Spears performed with 'NSYNC and Aerosmith during MTV's Super Bowl halftime show in January 2001.

NASCAR Nights: The Ballad of Britney Jean

Getty Images
Spears served as the Grand Marshal of the NASCAR Winston Cup Pepsi 400 race in July 2001.

Britney and Justin

Getty Images
Spears and former Mickey Mouse Club co-star Justin Timberlake were the golden couple of pop during their three year relationship, which the couple confirmed to the media in 2000.

I'm a Snake 4 U

Getty Images
Britney one-upped her own 2000 VMA striptease with a legendary snake routine during "I'm a Slave 4 U" at the 2001 MTV Video Music Awards.

The King and Brit

Getty Images
Spears performed with Michael Jackson during his 30th anniversary concert at Madison Square Garden in September 2001.

Crossroads

Paramount Pictures
Britney starred in her debut feature film Crossroads in 2002, with Orange is the New Black's Taryn Manning and Guardians of the Galaxy star Zoe Saldana.

Golden Couple

Getty Images
Britney and Justin attended the premiere of her movie Crossroads on Feb. 11, 2002.

Digital Dancing Queen

Getty Images
Britney was immortalized in her very own Playstation 2 game, Britney's Dance Beat, in 2002. The game included music videos in the gameplay background as the player auditioned to become one of Britney's backup dancers.

Sister Act

Getty Images
Britney and her sister Jamie Lynn Spears, a Nickelodeon star, presented together at the 2002 Teen Choice Awards. 

Brit's Bad Boy

Getty Images
After breaking up with Timberlake in late 2002, Britney was briefly linked to notorious Hollywood playboy Colin Farrell.

The Kiss Heard 'Round the World

Getty Images
During a performance of Madonna's "Like a Virgin" at the 2003 VMAs, Brit locked lips with the Material Girl herself. The scandalous moment was highly publicized and is still one of the pop stars' most famous moments.

She's a Star

Getty Images
Spears got her very own star on the Hollywood Walk of Fame on Nov. 17, 2003.

Britney and K-Fed

Getty Images
Britney met dancer Kevin Federline in April 2004. The couple was engaged three months later, and married in early October. The dramatic whirlwind relationship was chronicled briefly on the UPN reality show Britney & Kevin: Chaotic.

The Golden Ticket

Getty Images
Britney showed off her first pregnancy with a tank top reading "I have the Golden Ticket" as she and husband Kevin Federline walked the red carpet at the Charlie and the Chocolate Factory premiere in July 2005.

Back in Black

Getty Images
Spears had her hair dyed dark as she introduced husband Kevin Federline onstage at the Teen Choice Awards in August 2006, three months before the couple filed for divorce.

Gimme More

Getty Images
Brit Brit's return to the VMA stage in September 2007 was panned by critics and inspired the famous Chris Crocker "Leave Britney Alone!" reaction video. 

Queens Reunited

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Britney joined fellow queen of controversy Madonna onstage during Madge's Sticky and Sweet tour at Dodger Stadium in Nov. 2008.

In the Center of the Ring

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Britney took her Circus act overseas, performing at the Bambi Awards in Offenberg, Germany in Nov. 2008.

Personal Business

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Spears began dating her agent Jason Trawick in May 2010. The couple became engaged in December 2011, but ended their relationship in January 2013.

Brit Brit and RiRi

Getty Images
Spears performed with Rihanna at the Billboard Music Awards in May 2011.

Queens of Pop

Getty Images
Spears accepted the award for Best Pop Video from Lady Gaga's male alter ego at the 2011 Video Music Awards.

The X Factor

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Spears joined L.A. Reid, Demi Lovato, and Simon Cowell as a judge on the second season of the American version of The X Factor. Spears mentored the Teens category and her final act, Carly Rose Sonenclar, was the show's runner-up.

Sir Elton

Getty Images
A brunette Britney posed with Sir Elton John at the singer's AIDS Foundation Academy Awards Party in February 2013. 

Baseball Boys

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Britney smiled with sons Sean Preston and Jayden James at Dodger Stadium in April 2013.

Viva Las Vegas

Getty Images
In December 2013, Spears began her two-year residency in Las Vegas. Britney: Piece of Me debuted at Planet Hollywood Resort & Casino on Dec. 27.

People's Choice

Getty Images
Brit Brit looked glam and gorgeous accepting the People's Choice Award for Favorite Pop Artist in January 2014.

Lady in Red

Getty Images
Britney rocked a dark red hair color when she and boyfriend David Lucado attended Elton John's Academy Awards party in March 2014. 

The Intimate Britney Spears

Getty Images
Brit Brit unveiled her lingerie collection, The Intimate Britney Spears, in September 2014.

Britney Day

Getty Images
On Nov. 5, 2014, Britney joined Clarke County Commissioner Steve Sisolak and cast members from Jubilee to celebrate "Britney Day" in honor of the singer's Las Vegas residency.

Home for the Holidays

Instagram
In December 2014, Britney posed with sons Sean and Jayden and new boyfriend Charlie Ebersol in matching flannel in front of their Christmas tree.

Sports Star

Getty Images
Spears joined NFL star J.J. Watt onstage at the 2015 ESPY Awards in August to present the Best Female Athlete award to MMA fighter Ronda Rousey.

Style Icon

Getty Images
Brit Brit rocked rainbow hair at the Teen Choice Awards in August 2015, where the singer was honored with the Candie's Choice Style Icon Award.

VMA Legend

Getty Images

The singer gave host Miley Cyrus a run for her money at the 2015 MTV Video Music Awards, presenting the award for Best Male Video in a silver and gold ensemble.


'Tis the Season

Getty Images
Spears helped Las Vegas kick off the 2015 holiday season, pulling the switch to the light the Christmas tree at The LINQ Promenade on Nov. 21.

Lacy Lady

Britney Spears at 2016 billboard music awards
JB Lacroix/WireImage

After a few months out of the spotlight, the pop star looked on top of her game at the 2016 Billboard Music Awards in May, where she performed a medley of her hits.

Partner in Crime

G-EAZY and Britney Spears at 2016 mtv video music awards
Nicholas Hunt/FilmMagic

Three months later, Brit Brit rocked a daring cut-out LBD when she hit the white carpet for the 2016 MTV Video Music Awards with her "Make Me..." collaborator, G-Eazy.

Birthday Girl

Britney Spears 35th birthday
Christopher Polk/Getty Images for iHeartMedia

The pop princess giddily rang in the big 3-5 onstage during 102.7 KIIS FM's Jingle Ball 2016 concert on her actual birthday, Dec. 2. Her pigtails were very reminiscent of her first days on the music scene, however!

Nearly Naked

Britney Spears at pre-grammy gala in 2017
Kevin Mazur/WireImage

Spears opted for a very daring dress at a Pre-GRAMMY Gala in Los Angeles on Feb. 11, 2017.

Sugar High

Britney Spears with sons and niece at Planet Hollywood Disney Springs
Gerardo Mora/Getty Images for Planet Hollywood Observatory

Feeling like a kid again! Spears had a sweet time hanging with her sons, Jayden and Sean Federline, and her niece, Maddie Aldridge, at Planet Hollywood Disney Springs in Orlando, Florida, on March 13, 2017.

Basketball Babe

Britney and Sam at Lakers game
Allen Berezovsky/Getty Images

Spears wasn't afraid to pack on the PDA with boyfriend Sam Asghari at a Los Angeles Lakers vs. Golden State Warriors game at L.A.'s Staples Center on Nov. 29, 2017.

Goodbye, Vegas!

Britney Spears Las Vegas
Splash News

The mom of two closed out 2017 with a New Year's Eve performance that marked the end of her four-year residency at Planet Hollywood Resort and Casino's AXIS. She admitted to her Instagram followers that the final Britney: Piece of Me concert was "bittersweet."

Sparkly Stunner

Britney Spears in 2018
Axelle/Bauer-Griffin/FilmMagic, Jon Kopaloff/FilmMagic

Glittery outfits are kind of her thing! Spears stepped out in two sparkly looks within months of each other. She first donned a nearly naked sleeveless mini with strategically placed embellishments at the 4th Hollywood Beauty Awards in February 2018. Two months later, she went for an even more daring silver cut-out number at the 29th Annual GLAAD Media Awards.

Back on the Road

Britney Spears on tour in 2018
Kevin Mazur/BCU18/Getty Images for BCU

The princess of pop must've made Cher proud with these strappy ensembles during opening night of her Piece of Me Summer Tour on July 12, 2018.

Big Announcement

Britney Spears announces second vegas residency
Ethan Miller/Getty Images

Spears was all smiles when she announced her new Las Vegas residency, Britney: Domination, at Park MGM on Oct. 18, 2018. Unfortunately, she had a rough few months after sharing this news. Less than two months later, the pop star went on an indefinite work hiatus, putting the residency that was supposed to kick off on Feb. 13 on hold. Then in April 2019, she entered a facility to better care for herself following tremendous stress over her father, Jamie Spears', health crisis.

Celebrating Two Decades of Music

The singer's sophomore LP dropped on May 16, 2000 -- and Spears celebrated the memorable day with a special post on May 16, 2020. Sharing a compilation video on Instagram, the pop star shared a memory from when she released it and thanked her fans for "sticking with me." "Thank you to whoever made this ….. I just nearly dropped my phone I wasn’t expecting it ??? !!!!! 20 years since the Oops! ? album," she wrote. "The anticipation and the butterflies  I felt before it came out were crazy …. all of my expectations were exceeded !!!! And it’s all thanks to you folks …. thank you for sticking with me and growing with me. I am one Lucky girl ⭐️?PS you see even 20 years ago I still liked to twirl ???✨ !!!!" 



Around the same time, Brit Brit was still battling for autonomy over her finances. The 38-year-old singer has been under a conservatorship since 2008, a legal concept in which a judge appoints a responsible person or organization to act as the legal guardian, making the calls on everything from finances to personal decisions for the conservatee. After Britney's father, Jamie Spears, stepped down as her conservator last September, the singer's longtime care manager, Jodi Montgomery, took over. However, her mother, Lynne, filed a request with the Los Angeles County Court on Monday, hoping to receive special notice on "all matters" in regard to Britney's SJB Revocable Trust. "Britney has always struggled with her mental health so Lynne's concern for Britney is never-ending. She is her mother and hates to see her suffer," a source told ET in July 2020. "Lynne filed for transparency to keep an eye on the finances because she knows Britney has her ups and downs. She has been doing much better; she is in regular therapy and exercising. Lynne sees a huge improvement."


Peachy and Pearls

Britney posted an Instagram pic of herself wearing a peach puffy sleeve top with a pearl necklace on Nov. 18, 2021.


Pink Flowers and Tube Socks

The pop star wore a pink flower top, black skirt, and white socks with pink stripes on June 4, 2022. 


Britney and a Pup!

Britney shared a pic of herself on Instagram, sporting a sundress and a tan hat alongside an adorable dog on July 12, 2023. 


Married and Divorced

Britney Spears and Sam Asghari
Kevin Winter/Getty Image

Britney and Sam Asghari married in June 2022 and then Sam filed for divorce in August 2023.


Horse Riding

Britney shared a video of her riding horses in Mexico on June 24, 2024. 


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