Britney Spears may have made her television debut on Star Search, but her first big break came in the early '90s as she starred alongside Justin Timberlake, JC Chasez, Christina Aguilera, Ryan Gosling and Keri Russell on Disney's The Mickey Mouse Club.
“…Baby One More Time”
Spears officially shimmied onto the pop scene with the video for 1999's "…Baby One More Time," in which the pop star wore a midriff-baring schoolgirl uniform that some thought was too mature for the then-17-year-old.
Rolling Stone Cover
Spears created her first major controversy with this April 1999 cover of Rolling Stone. Her barely there attire raised eyebrows and led the American Family Association to call for "God-loving Americans" to boycott the pop star.
Dating Justin Timberlake
Shortly after she launched her pop career, Spears began dating her former Mickey Mouse Club castmate Justin Timberlake, but the couple split in 2002.
2000 Video Music Awards
While promoting her current album, Oops!… I Did It Again, Spears used MTV's Video Music Awards 2000 as a platform to show the world that she, truly, was not that innocent. Mid-performance, the then-18-year-old stripped off a classic black suit to reveal a flesh-colored, sparkly bodysuit underneath as she danced and writhed around onstage. It was the first of what would become a string of racy VMA performances for the singer.
“I’m a Slave 4 U”
Spears upped the ante the following year at the 2001 VMAs with a saucy performance of her newest hit, "I'm a Slave 4 U." The PETA-angering — but memorable — stunt included a large python and a tiger in a cage.
Spears made her big-screen debut in the Shonda Rimes–penned Crossroads, opposite Zoe Saldana and Taryn Manning. Paramount's 2002 teen road-trip dramedy was reportedly filmed on a $12 million budget and has earned more than $61 million to date.
The Kiss Seen ‘Round the World
Opening the 2003 VMAs alongside Christina Aguilera and Madonna — performing the latter's hit "Like a Virgin" — Spears found herself the talk of the night when she not only locked lips with the iconic diva, but slipped her the tongue. The brief moment remains one of the most memorable (and buzzed about) of Spears' career.
Spears wears nothing but diamonds in the music video for her 2003 hit "Toxic," which won the pop star her first and only Grammy for Best Dance Recording.
Chaotic is one way to describe Spears' tumultuous relationship with her second husband, Kevin Federline.
The singer made headlines in January 2004 when she married childhood friend Jason Alexander in Las Vegas, only to have the marriage annulled 55 hours later. By July of that same year, Spears announced that she was engaged to Federline — her former backup dancer — and the two wed in September. Their relationship was documented in the short-lived reality TV program Britney & Kevin: Chaotic, which aired on UPN in 2005.
In November 2006, Spears filed for divorce.
Following the birth of two sons and a failed marriage, Spears suffered through a public meltdown that culminated in the pop star being placed under the conservatorship of her father. In the early stages of her meltdown, February 2007, to be specific, photogs captured images of the then-25-year-old shaving her own head at a hair salon in Tarzana.
It was during this time that Spears also released her fifth studio album, Blackout, featuring the singles "Gimme More" and "Piece of Me."
‘Piece of Me’
In one of the most personal videos of her career, Spears directly addressed the media circus surrounding her in "Piece of Me." The clip went on to win Best Female Video, Best Pop Video and Video of the Year at the 2008 VMAs.
‘How I Met Your Mother’
Spears guested on a 2008 episode of How I Met Your Mother in which she played a receptionist. The gig brought in record ratings for the show and provided a much-needed image boost for the then-troubled Spears.
Spears embarked on The Circus tour in March 2009 to support her sixth studio album (her fifth to debut at No. 1 on the Billboard 200 chart). The timing marked the end of a tumultuous chapter in her life (months earlier, Spears and her father had obtained a restraining order against the singer's former manager, Sam Lutfi, ex-boyfriend/paparazzo Adnan Ghalib, and attorney Jon Eardley) and the beginning of a new, more peaceful era.
Relationship with Jason Trawick
Spears began dating her agent, Jason Trawick, in 2010, though the couple separated briefly in an effort to keep their relationship professional. In late 2011, the two became engaged and Trawick was named Spears' co-conservator alongside her father. There wasn't a happy ending for this love story, as the duo called off their engagement (and Trawick's co-conservatorship) in January 2013.
Spears was honored with a tribute episode on Fox's smash hit musical series Glee. Titled "Britney/Brittany," the episode saw actress Heather Morris (Brittany) in an anesthesia-induced hallucination in which she re-created several of Spears' most iconic career moments.
Spears appeared in multiple cameos during the hour-long broadcast.
‘Femme Fatale’ Tour
Spears embarked on the hotly anticipated Femme Fatale tour in June 2011 alongside Nicki Minaj. The tour was ranked No. 19 on Billboard's Top 25 Tours of 2011 and for those who weren't able to snag tickets, the Toronto show aired on Epix in a special titled Britney Spears Live: The Femme Fatale Tour.
Spears joined Simon Cowell, Demi Lovato and L.A. Reid as a judge on the second season of The X Factor USA, where she mentored the kids category. With a reported salary of $15 million, Spears became the highest paid judge on a TV singing competition series in history.
Clearly uncomfortable in both the realm of live television, as well as doling out criticism, Spears did not return for another season.
Las Vegas Residency
After months of speculation, Spears made her Las Vegas residency official with an announcement on Good Morning America. The 31-year-old will perform a total of 100 shows — 50 in 2014 and 50 in 2015 — at Planet Hollywood. The show is appropriately titled "Piece of Me."
At home, Spears plays mom to sons Sean Preston (born September 2005) and Jayden James (born September 2006). Both her kids (and her niece, Maddie) were in the music video for "Ooh La La," featured on the Smurfs 2 soundtrack in 2013.