A Look Back At Britney Spears & Justin Timberlake's Popstar Romance

Britney Spears and Justin Timberlake made up one of the most iconic celebrity couples in the late ‘90s and early 2000s. Besides the fact that they were young popstars, who doesn’t love a good story of childhood sweethearts ending up together? Their romance was a highly publicized affair, and as a couple, their love seemed to burn the brightest. Despite its intensity, it came to an end barely three years after it started. In the years that followed, there have been speculations and theories from fans about what really went down. 

Through songs and indirect comments, the two have given brief insights on their respective versions of events. Britney Spears’ memoir, The Woman In Me, was released in October 2023. The book revealed previously unknown details about her relationship with Timberlake that left fans shocked. Two decades after their break up, their history still haunts them, and the media remains interested. Following Timbaland's recent comments (and apology), let’s take a look back at their infamous romance. 

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Britney Spears and Justin Timberlake first met in 1992 on the set of Disney’s show, The All-New Mickey Mouse Club. They were cast as “Mouseketeers” alongside now-iconic figures like Christina Aguilera, Ryan Gosling, and Keri Russell. Spears and Timberlake were both only 11 years old in 1992, so obviously, their relationship is believed to be purely platonic at the time. The All-New Mickey Mouse Club was subsequently canceled in 1994. However, the two were already good friends by then, and their friendship eventually blossomed into a romantic relationship. 

Timberlake shared in a 2006 interview with GQ, “I was in love with her from the start. I was infatuated with her from the moment I saw her." More recently, Spears divulged in her memoir, “(Once) at a sleepover, we played Truth or Dare, and someone dared Justin to kiss me.” Well, he did reportedly kiss her as a Janet Jackson song played in the background. Evidently, their time together on The All-New Mickey Mouse Club set the tone for their eventual relationship.

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After leaving their Mouseketeering days behind in 1994, the two moved on to other things. Justin Timberlake became a member of *NSYNC in 1995, serving as one of the boy band’s two lead singers. Likewise, Spears was briefly a member of the girl group Innosense before she secured a solo deal with Jive Records in 1997. To promote her upcoming debut album, Britney Spears would eventually tour with *NSYNC in 1998, serving as an opening act. While the pair may have kept in touch over the years, their time together on tour took their relationship to the next level.

Britney Spears and Justin Timberlake became a couple in 1999 but initially did not reveal this to the public. The two initially denied rumors of their relationship during the early stages. However, that could only go on for so long, and they eventually went public with their relationship later in 1999.

The pair were teenagers when their relationship started, and were arguably the most iconic teenage couple at the time. From their red carpet debut in 2000, the media, as well as the fans around the world, couldn’t get enough. In 2000 and 2001, they were often seen together and shared some iconic fashion moments. For example, their insanely fashionable matching denim looks at the 2001 AMAs are forever etched in our minds. So also are their adorable  “Pinky” and “Stinky” matching jerseys from a charity basketball event in 2001.

In a 2001 interview with Andi Peters for Rich & Famous, Spears shared that Timberlake asked her out sometime in 1999, while they were on tour. Many fans wholeheartedly hopped on the Britney Spears and Justin Timberlake train, rooting wildly for the pair. Admittedly, what the public could see about their relationship was as cute as cute could get. Surprisingly, however, their relationship came to an unexpected end in March 2002.

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Following their break up, Spears and Timberlake both went through varying degrees of heartbreak. In November 2002, Timberlake released the video for his acclaimed song “Cry Me a River,” which he admitted was inspired by Spears. Subsequently, Britney released “Everytime,” a song widely considered to be a response to “Cry Me a River” in 2004. Timberlake was interviewed by Barbara Walters in 2002, and when he was asked why the breakup happened, he answered “…I promised her that I wouldn’t say specifically why we broke up.” 

Similarly, on an episode of Primetime, Diane Sawyer pointedly asked Britney Spears what she did that caused Timberlake so much pain and suffering. "I was upset for a while. I think we were both really young, and it was kind of waiting to happen,” she said. She continued by saying she “will always love him, and he'll always have a special place in my heart.” However, Sawyer pressed further, “He left the impression that you weren't faithful, that you betrayed the relationship.” To that, Spears responded, “I think everyone has a side of their story to make them feel a certain way. I'm not technically saying he's wrong, but I'm not technically saying he's right either.”

Read More: Britney Spears Recalls Justin Timberlake Breakup, Says She Should’ve “Slapped” Mom & Sister

The Princess of Pop released her memoir, The Woman In Me, in October 2023, and even before it dropped, the book was already shaking tables. The Woman in Me details much of the superstar’s troubled upbringing and sees her being the most vulnerable she’s ever been. Additionally, the book contains some never-before-seen information about Spears’ time with Timberlake. In an excerpt from the memoir, the singer revealed that she became pregnant with Justin’s child at some point in their relationship. However, even though she’d have liked to keep the baby, she sadly had to undergo an abortion because “Justin definitely wasn’t happy about the pregnancy. He said we weren’t ready to have a baby in our lives, that we were way too young.” Moreover, she claimed in the book that Timberlake broke up with her via text. 

From singing and dancing together as kids, to donning matching outfits as teenagers, Britney Spears and Justin Timberlake were one of the most famous couples of the pop culture wave of the 2000s. They have since gone their separate ways. While Justin Timberlake married actress Jessica Biel in 2012, Britney Spears has had her fair share of love, although she is now single. With the revelations in her memoir, however, it’s especially easy to see that things were not as rosy as the public image that was presented. 

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