Britney Spears' Rollercoaster Career and Personal Life Throughout the Years

Britney Spears is one of the most famous pop stars on the planet, having been in the spotlight since her early teens when she first hit television screens as a member of The Mickey Mouse Club.

The Louisiana native has sold over 150 million records worldwide, is the best-selling female artist of the ’00s, has won a Grammy Award, seven Billboard Awards, earned five No. 1 hits and has a star on the Hollywood Walk of Fame. She has also launched a perfume line, acted in movies and on television shows, served as a judge on The X Factor and headlined a successful Las Vegas residency.

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She’s also had her share of personal struggles, which included reported addiction and custody issues with her sons and is under an ongoing conservatorship. Spears has been married twice and is currently dating boyfriend Sam Asghari.

Read on for a look back at the singer’s decades-long journey through fame.

1998

After starring on the revival of The Mickey Mouse Club from 1992-1996, Spears returned to spotlight in 1998 with her debut single “…Baby One More Time,” which would go on to cement her as one of the biggest pop stars of her time. She released her debut album of the same name in January 1999 and followed that with 2000’s Oops!…I Did It Again, which broke the SoundScan record for the highest debut sales by any solo artist and is currently one of the best-selling albums of all time.

2001

Spears continued her professional rise for the next several years, developing a more provocative image with performances including multiple outings at the MTV Video Music Awards — notably her iconic performance with Banana the snake in 2001 and her kiss with Madonna in 2003 — as well as her next two albums, 2001’s Britney and 2003’s In the Zone. She also dated *NSYNC member Justin Timberlake throughout much of her early career, with the pair splitting in 2002.

2004

In January 2004, Spears married childhood friend Jason Alexander in a ceremony in Las Vegas, with the union annulled 55 hours later. That September, she married backup dancer Kevin Federline, and the pair welcomed two sons — Sean Preston in September 2005 and Jayden James in September 2006. Spears filed for divorce from Federline in November 2006 and the divorce was finalized in July 2007. In 2018, Federline requested more child support from Spears, with their legal battle ending in 2018.

2007

Notoriously Spears’ most difficult personal year, 2007 saw the star shave her head in February and subsequently attack a photographer’s car with an umbrella one day after staying in a drug rehabilitation facility for less than a full day. In October, she lost custody of her sons to Federline, the same month she released her album Blackout. To promote the project, she performed lead single “Gimme More” at the 2007 MTV Video Music Awards in a performance that was universally panned and is considered one of her lowest professional moments.

2008

In 2008, Spears was placed under the conservatorship of her father, Jamie Spears, a ruling that is still in effect today. The conservatorship was instated after Spears refused to relinquish custody of her sons and was hospitalized at Cedars-Sinai Medical Center in January 2008. Her visitation rights were suspended the next day and she was later committed to the psychiatric ward of Ronald Reagan UCLA Medical Center and put on 5150 involuntary psychiatric hold before being released five days later.

In December of that year, the star released her album Circus, which solidified her professional comeback and led her to hit the road on tour for the first time in years.

2013

The singer’s professional career continued its upswing as she released multiple albums including 2011’s Femme Fatale, which she supported with a tour, and 2013’s Britney Jean. In December 2011, she became engaged to her former agent Jason Trawick, with the pair splitting in January 2013. In December of that year, Spears began her first Las Vegas residency, Britney: Piece of Me, at Planet Hollywood Resort & Casino. It ran until December 2017 and kick-started the trend of major stars heading to Vegas for their own residencies. She released her ninth studio album, Glory, in 2016.

2019

After announcing her second Las Vegas residency, Britney: Domination, in October 2018, Spears revealed in January 2019 that she would be putting the show on hold in order to take care of her father, who had suffered a ruptured colon in November 2018. In April, it was reported that Spears had checked herself in to a mental health facility in order to focus on her health as she dealt with her father’s illness. The 37-year-old is currently on an indefinite work hiatus.