A look back at Britney Spears, Justin Timberlake romance

Britney Spears and Justin Timberlake's relationship was a highly publicized romance that began in the 1990s during their rise to fame as pop stars. 

Below is a timeline that provides an overview of their relationship, from their initial connection as child stars to their shared fame, fashion moments, breakup and their enduring status as pop culture icons in their own right.

The famous singer and former member of NSYNC were in a romantic relationship from 1999 to 2002, but Timberlake reportedly ended things with Spears through a text message. The period that followed was difficult for the "Toxic" singer. She recounts in her memoir that she rarely ventured outside her home in the wake of their breakup.

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The pop icon regarded her song "Everytime" as one of the most intimate tracks on her 2003 album, "In the Zone." This song was released in the aftermath of her widely publicized split with Timberlake in 2002 after a three-year relationship.

A new perspective on "Everytime" emerged recently as Spears wrote about the song in her memoir, "The Woman in Me," which was published in October 2023. She disclosed that during their relationship, Timberlake got her pregnant and she underwent an abortion. 

Spears wrote that Timberlake was not happy about the pregnancy and that if it were up to her, she would have kept the baby. She said the event is still "agonizing" to her to this day.

Britney Spears and Justin Timberlake both start out as members of the "Mickey Mouse Club," a popular Disney TV show.

Britney and Justin's paths cross again as they become part of two of the era's biggest pop groups – Britney with NSYNC and Justin with the Backstreet Boys.

The two young pop stars officially become a couple. Their relationship is kept relatively private at the time.

Britney and Justin make headlines when they attend the American Music Awards wearing iconic matching denim outfits.

The high-profile couple goes through a much-publicized breakup, which fuels media speculation and tabloid frenzy.

After their breakup, both Britney and Justin release songs that are rumored to be about each other. Justin's "Cry Me a River" and Britney's "Everytime" are often seen as musical responses to their history as a couple.

Media outlets report a brief reconciliation, but it does not lead to a long-term reunion. Despite the ups and downs, Britney and Justin have since spoken about their continued friendship and mutual respect in various interviews.

Both artists went on to achieve immense success in their respective careers, becoming two of the biggest names in the music industry. Over the years, Britney and Justin have both faced personal challenges and triumphs, with their relationship largely remaining a part of their past.