Making Of A Superstar: Britney Spears’ Blockbuster 1999

Mike Wass | April 16, 2020 2:20 pm
Lost Hit: Britney's 'Passenger'
Britney Spears should have released 'Passenger' as single from 'Britney Jean.'

Britney Spears was the biggest pop star in the world in 1999. “…Baby One More Time” broke every chart record in late 1998, paving the way for the then-teenager’s debut — also called ..Baby One More Time — to become one of the highest-selling albums of all time. It quickly earned a diamond certification in the US (for shipments in excess of 10 million copies) and is estimated to have sold more than 25 million copies around the world. And that’s because it had HITS.

Imagine following up “…Baby One More Time” with the one-two punch of “Sometimes” and “(You Drive Me) Crazy.” Britney was selling so many copies that Jive Records didn’t even bother releasing “Born To Make You Happy” in the US, which is wild considering that it is the best song on the album. Over the course of 1999, the Instagram icon not only transitioned from rising star to history-maker. She also rebranded entirely, going from brown-haired Girl Next Door to racy blond bombshell in less than 12 months.

Click through our gallery of Britney’s best looks from 1999 above and revisit “Sometimes” below for an instant boost of serotonin.

What was your favorite look? Let us know below, or by hitting us up on Facebook and Twitter!