Britney Spears Through the Years

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.

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

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.

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.

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."

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

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

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.

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.

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

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.

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

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.

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

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

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.

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

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.

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.

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.

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. 

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

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

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

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

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

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.

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

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

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.

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

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

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

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.

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

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.

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.

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 super skimpy silver and gold ensemble.

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.

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.

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.

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!

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

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.

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.

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."

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.

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.

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.

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."