Let’s be honest: Britney Spears requires no introduction. The singer, dancer, actor and undeniable tabloid fixture has dominated popular culture since she stepped onto the entertainment scene in the late ’90s. December 2 is Spears’ 40th birthday, which means it’s the perfect time to celebrate her lifetime’s worth of achievements thus far.
From the moment she uttered that first breathy “Oh, baby, baby” in her debut single “…Baby One More Time,” the music game was officially changed. Fast-forward to today, and the world’s watchful eyes continue to be glued to Spears’ every move. (Have you checked out her fantastic Instagram presence lately? She’s got more than 35 million followers.)
Spears has more than a few memorable milestones to come out of her decades-long career. In fact, it’s hard to narrow down the influential artist’s standouts. Her lyrics, outfits and even choreography will be burned into the brains of fans forever. We’re taking a look back at a timeline that highlights some of her most iconic moments ever. You want a piece of her? It’s time for a trip down Britney Spears memory lane.
A version of this article was previously published in November 2018.
1993: Britney Spears Stars on ‘The Mickey Mouse Club’
At just 12 years old, Spears became a Mouseketeer on Disney Channel’s The All New Mickey Mouse Club alongside fellow future superstars Christina Aguilera, Justin Timberlake and Ryan Gosling.
“It was a really good time,” Spears said of the experience, speaking with Entertainment Tonight in 2018. “It was a great time. It was probably one of the most special times in my life, The Mickey Mouse Club.”
1997: Britney Spears Signs With Jive Records
In 1997, 15-year-old Spears — a relative unknown at the time — signed a contract with Jive Records and moved from Louisiana to New York City.
November 1998: ‘…Baby One More Time’ Video Released
Spears became an instant household name when “…Baby One More Time,” a single from her debut album of the same name, took the world by storm. The high school-set clip is one of the most recognizable music videos of all time.
“She said, ‘I want to be in a school with a bunch of cute boys and do some dancing,'” director Nigel Dick told EW in 2018, reflecting on Spears’ vision.
1999: Britney Spears & Justin Timberlake Become America’s Sweethearts
Friends since their Mickey Mouse Club days, Spears and NSYNC boy-bander Justin Timberlake were in a romantic relationship from 1998 until 2002. These two seemed like a match made in pop-star heaven to their adoring public.
“I was in love with her from the start,” Timberlake revealed to GQ in 2006. “I was infatuated with her from the moment I saw her.”
September 2000: MTV Video Music Awards Performance
Britney Spears wowed the crowd at Radio City Music Hall in 2000 with a knockout performance at the VMAs. She ripped off a suit to reveal a glitzy flesh-tone number after crooning the Rolling Stones classic “Satisfaction” before launching into her hit “Oops… I Did It Again.” The moment will go down in MTV history, but it definitely wasn’t the last time she made buzzed-about waves at the award show.
April 2000: ‘Oops! …I Did It Again’ Video Premieres
Red latex bodysuit? Check. Astronaut love interest? Check. Titanic reference? Check. Spears’ cosmic “Oops! …I Did It Again” music video had it all and remains one of the most unforgettable creations to emerge from MTV’s TRL era.
“This whole idea was my idea. I was like, ‘I want to be on Mars, dancing on Mars,'” Spears declared in an episode of Making the Video, via Billboard.
January 2001: AMAs Double Denim Look
The couple that rocks matching denim ensembles together stays together? Not quite. But Spears and Timberlake created a future meme-able moment at the 2001 American Music Awards that will be imitated for eternity.
January 2001: Super Bowl Halftime Show
Aerosmith, NSYNC, Nelly, Mary J. Blige and Britney Spears? The Super Bowl XXXV halftime show was a veritable who’s who of early 2000s musical greatness. We’ll never forget everyone singing “Walk This Way” (or Spears’ fashionable arm socks).
September 2001: MTV Video Music Awards Performance
Could Spears possibly top her 2000 MTV Video Music Awards sparkly striptease extravaganza? Yes, yes she could. The superstar sang “I’m a Slave 4 U” while holding a live python.
February 2002: Britney Spears Stars in ‘Crossroads’
Lights. Camera. Britney!
Spears made her big-screen debut starring in the Shonda Rhimes-penned (yes, that Shonda Rhimes) dramedy Crossroads alongside Zoe Saldana, Taryn Manning and Anson Mount. She also performed songs from her third studio album, Britney, including “I’m Not a Girl, Not Yet a Woman.”
August 2003: MTV Video Music Awards Performance With Madonna
Spears got major media attention for yet another VMAs performance to remember in 2003. She and Christina Aguilera surprised audiences when they locked lips with none other than the Queen of Pop herself, Madonna.
January 2004: ‘Toxic’ Video Premieres
Spears continued to be a music video force to be reckoned with when she debuted the colorful clip for the catchy dance hit “Toxic,” a favorite from her fourth studio album, In the Zone.
“Toxic” landed Spears her first and only Grammy. She won in the best dance recording category.
2004–2006: Britney Spears Dates & Marries Kevin Federline
After making headlines for spontaneously tying the knot with childhood pal Jason Alexander in Las Vegas on New Year’s 2004 (the marriage only lasted 55 hours), Spears engaged in a whirlwind romance with backup dancer Kevin Federline. The pair confirmed their engagement in June 2004 and got hitched in September of that year.
Unfortunately, Spears filed for divorce just two years later, in November 2006. She and Federline have two children: sons Sean Preston and Jayden James.
September 2007: ‘Gimme More’ at the MTV Video Music Awards
Spears endured a tumultuous year in 2007 that included shaving her head in front of the paparazzi and entering rehab. She returned to her old stomping grounds for a performance of “Gimme More” at the VMAs that year, but the lackluster result wasn’t the comeback she probably hoped for.
Spears debuted her fifth studio album, Blackout, in October 2007. Despite the VMAs mishap, the edgy work is considered a critical darling.
2008: Britney Spears Guest Stars on ‘How I Met Your Mother’
Spears showed off her comedic chops portraying receptionist Abby on two 2008 episodes of the hit CBS sitcom How I Met Your Mother. According to the New York Times, her star power skyrocketed the series to its highest ratings that year.
October 2008: Britney Spears Releases ‘Womanizer’
Spears was well on her way to dominating the pop scene again after releasing “Womanizer,” the lead single from her successful sixth studio album, Circus. The track was accompanied by a lively video featuring Spears in a variety of costumes and was the first Britney Spears song to top the Billboard Hot 100 charts since 1999’s “…Baby One More Time.”
September 2010: ‘Glee’ Appearance
Just call it the Britney effect.
Spears made a cameo in Glee‘s “Britney/Brittany” episode during the show’s second season. The concept was a ratings record-breaker for the highly popular series.
September 2011: Acceptance of the Michael Jackson Video Vanguard Award
Britney Spears’ vast and influential contribution to music video history didn’t go unnoticed. MTV awarded her the esteemed Michael Jackson Video Vanguard VMA in 2011.
2012: ‘X-Factor’ Judge Stint
Spears added the title of reality TV judge to her résumé when she joined Fox’s The X-Factor for its second season, taking over for Nicole Scherzinger and Paula Abdul.
2013–2017: Vegas Residency
Spears took her talents to Vegas in 2013 for a concert residency at Planet Hollywood. The show, Britney Spears: Piece of Me, became a huge success and even launched a tour of the same name.
Piece of Me may have concluded in 2017, but Spears isn’t done with Sin City just yet. She announced a new residency in October 2018 titled Britney: Domination. The show was set to kick off at the Park Theater at the new Park MGM resort in February 2019.
2020: The Battle for Britney’s Freedom
Once Spears’ Las Vegas residency came to an abrupt hault, longtime fans began to wonder what the pop star was going through. While there were mixed messages from her social media account, many started to consider that perhaps Spears and her family were clashing over her years long conservatorship.
The #FreeBritney movement began in April 2019, and gained momentum well into 2020, as Spears’ conservatorship and questions around its validity after more than a decade in place by her family was even necessary. You know how we mentioned the Britney effect? This reached a whole new level.
2021: Britney Spears’ Emotional Testimony
By June 2021, Spears finally had the chance to speak and share just a fraction of what she’d endured under her restrictive conservatorship. “I want to be able to get married and have a baby. I was told right now in the conservatorship, I’m not able to get married or have a baby, I have a (IUD) inside of myself right now so I don’t get pregnant,” Spears revealed in her testimony.
“I wanted to take the (IUD) out so I could start trying to have another baby. But this so-called team won’t let me go to the doctor to take it out because they don’t want me to have children – any more children.”
September 2021: Britney Spears Gets Engaged
Amid the drama of her conservatorship, Spears did have an exciting milestone to celebrate with her longtime love, Sam Asghari. The couple got engaged in September 2021, and they couldn’t have been happier — sharing the news on Instagram. “I can’t f*cking believe it,” Spears wrote as the caption to her video post.
November 2021: Britney Spears Gets Her Freedom
By mid-November, the conservatorship that dictated Spears’ life for more than a decade finally came to an end. With the court’s ruling, Spears regained autonomy over her body and finances and is now able to determine her own work schedule. To celebrate, Spears took to Instagram and shared a video of her fans celebrating outside of the court house. “Good God I love my fans so much it’s crazy !!! I think I’m gonna cry the rest of the day !!!! Best day ever … praise the Lord … can I get an Amen ???? #FreedBritney.”
November 2021: Ready for a New Start
With her freedom and autonomy restored, Spears is ready for a whole new chapter to begin in 2022. “I’m just grateful for each day, and being able to have the keys to my car; being able to be independent and feel like a woman; owning an ATM card, seeing cash for the first time,” she said in part in a November 2021 video.
More than anything, Spears is ready to be an advocated for people with “real disabilities and real illnesses.” Once again, Spears also thanked the #FreeBritney movement, saying, “Because of you, I honestly think you guys saved my life in a way.”
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