After much speculation, Britney confirmed that she was dating *NSYNC superstar Justin Timberlake. The surface made it seem like a fairy tale romance. The lovebirds were on cloud nine, wearing the infamous matching denim outfits at the American Music Awards.
They even wore matching basketball jerseys at a charity basketball game, emblazoned with their nicknames for each other – Stinky for Timberlake, and Pinky for Spears. Fans loved the power couple, and so were shocked when they split in 2002. Rumors started to emerge before long. JT would eventually spill all the beans in one of his early solo songs.
Baby One More Time
Jive Records wanted the music video for Spears's titanic single to be animated. It was Britney herself who disagreed, instead suggesting that she be dressed as a Catholic schoolgirl. “...Baby One More Time” sold half a million copies on its first day and hung out at the top of the Billboard Hot 100 for two consecutive weeks.
It's become one of the best-selling singles of all time and almost single-handedly revitalized teen pop. All of this stardom, success, and money happened before Spears even turned twenty years old. Britney's star was rising, but that doesn't mean it would always be easy.
She Did it Again
Britney Spears's second studio album came out in May of 2000. "Oops!... I Did It Again" debuted at number one in the United States, selling 1.3 million copies, breaking the record for the highest debut sales of any solo artist. This album has sold more than twenty million copies worldwide. The same year, Spears set out on her "Oops!... I Did It Again Tour," grossing $40.5 million.
She released a book, "Britney Spears' Heart to Heart," which she co-wrote with her mom. In September 2000, she performed at the MTV Video Music Awards. She began the performance as normal, but halfway through, she ripped her black suit off to reveal a much more risque flesh-colored bodysuit and provocative dance routine.
He's Not Fooling Anybody
Not long after this star-studded split, Timberlake released the song “Cry Me a River” in December 2002. Fans loved the haunting, beautiful lyrics, but it didn't take a genius to point out the similarities between the female star in the music video and Spears. While Timberlake has never publicly acknowledged who the song is about...we all know who it is.
He's even said that he wrote the song in the span of two hours, immediately following the breakup. Spears wrote a song in response: “Everytime,” with her friend's help and backing vocalist Annet Artani. The ballad couldn't defeat Timberlake's song, though.
Timberlake is Doing Fine
One of the longest-running and most prevalent rumors about the breakup is that Spears cheated on Timberlake with choreographer Wade Robson. Britney tried to hide the affair from Justin's eyes, but he discovered it nonetheless. Despite it all, it seems like Timberlake has ended up with a pretty wonderful life: he's married to the beautiful Jessica Biel, they have two children together.
Based on his 2019 album "Man of the Woods," he has a handsome log cabin in the woods where he sits to write his music and get away from it all. Spears’s life has gone through many ups and downs, but she can't claim the storybook life of Timberlake.