Britney Spears & Justin Timberlake’s Romance Timeline: Meeting On ‘Mickey Mouse Club,’ Dating & More

Britney Spears and Justin Timberlake were one of the hottest couples of the late '90s and early aughts. Following Justin's show of support for Britney after her conservatorship hearing, look back at their past romance.

Britney Spears, Justin Timberlake
Image Credit: AP

Britney Spears and Justin Timberlake were the prince and princess of pop in the late ’90s and early aughts. The two, who’d known each other since they were youngsters, had a highly publicized romance and an even more scrutinized breakup. Following Justin’s strong message of support for Britney amid her 13 year conservatorship and June 23 court hearing, take a look back at the one-time couple’s iconic romance.

How Did Britney & Justin Meet?

The cast of ‘The All-New Mickey Mouse Club’ [Everett].
In 1992 Britney and Justin were cast on The All-New Mickey Mouse Club. At the time, Britney and Justin were roughly 11 years old and were joined by other well known cast members like Christina Aguilera and Ryan Gosling. The series ran from 1993-1996. By the time the series wrapped, Britney and Justin parted ways. Britney returned to Mississippi but eventually came back to New York City with aspirations of a singing career. Justin, meanwhile, became a member of the boy band NSYNC. As the respective stars began to find more and more success in their careers, their paths eventually crossed again.

When Did Britney & Justin Start Dating?

Justin and Britney started dating in 1999 [Mega].
Britney and Justin started dating in 1999 and practically became pop music royalty. At the time that the two started dating, their careers had reached completely new heights. Britney’s hit tracks “Oops…I did It Again” and “…Baby One More Time” each were major successes with iconic music videos to boot. Justin and the boys of NSYNC became global sensations with their debut, self-titled album. Due to the success of both young stars, it was only a matter of time before they took the stage together.

Britney & Justin Performed On Stage

Justin and Britney perform with Aerosmith and more and the 2001 Super Bowl halftime show [AP].
On January 28, 2001, fans of Britney and Justin were treated to a joint performance by the pair at the Super Bowl XXXV halftime show. NSYNC joined rock band Aerosmith on stage for a medley, before Britney and a slew of stars (Mary J. Blige and Nelly, among them) joined for a rendition of Aerosmith’s hit with Run DMC “Walk This Way.” The performance was totally electric, but the best was still yet to come from Justin and Britney.

Britney & Justin Attend The 2001 AMAs

Justin and Britney at the 2001 American Music Awards [AP].
As their relationship progressed, Justin and Britney began making more public appearances at major industry events. One of the couple’s most iconic moments came at the 2001 American Music Awards in January 2001, just weeks before their joint Super Bowl performance. While walking the red carpet, Justin and Britney wore matching, head to toe denim outfits.

In the years since the pair walked the red carpet together, both have commented on the fashion choice. In a recent interview with The Hollywood Reporter, Justin confessed that there were certain “regrets” he had when it came to his fashion sense in the early years of his career. “I confess that there was maybe a period in the ’90s where I could skip over some of the outfits that were public,” he shared.

Britney, on the other hand, looked back on the moment fondly. “I guess my denim was a hit years ago,” Britney commented on a photo of two toddlers recreating the outfit. But the denim-on-denim look wasn’t the only matching ensemble that Justin and Britney fashioned. During a charity basketball game in July 2001, the couple wore matching jerseys with the phrase “Stinky 1 1/2” on Justin’s jersey and “Pinky 1/2” on Britney’s jersey. While the two were known for their matching looks, they also brought out their individual style at events, as well.

Justin & Britney Attend The ‘Crossroads’ Premiere

Britney and Justin at the premiere of “Crossroads” in 2002 [AP].
In February 2002, Justin supported Britney at the premiere of her film Crossroads, co-starring Zoe Saldana and Taryn Manning. The two looked super cute together and held hands on the red carpet. Sadly, this was one of the last public appearances the two would make together before they went their separate ways.

Britney & Justin Breakup

Justin and Britney broke up in 2002 [Mega].
By March 2002, Britney and Justin’s relationship ended, with the two confirming the news months after the fact. The couple’s split rocked pop culture, especially considering that the two were together for roughly three years. Although their relationship was officially over, the months to come would prove that both Justin and Britney had their romance and breakup on their mind.

Justin Releases ‘Cry Me A River’

Justin released “Cry Me A River” at the end of 2002 [AP].
In December 2002, Justin released the song “Cry Me A River,” which included lyrics that heavily indicated a past relationship he had. The subsequent music video, however, caused an even bigger stir. The visual accompaniment to the song featured a Britney Spears look-alike, and insinuated that Britney had cheated on Justin during their relationship.

Britney Releases ‘Everytime’

Britney Spears released “Everytime” in 2003, a song rumored to be a response to “Cry Me A River” [AP].
In 2003, Britney seemingly responded to the track with her own ballad. “Everytime,” a single off of her album In The Zone, took a more contemplative, soulful tone than what fans were accustomed to hearing from Britney. The singer has never confirmed or denied that the song is about her former flame, though fans to this day read into the lyrics as being about Justin and the former couple’s relationship.

Britney’s Interview With Diane Sawyer

Britney Spears sat down for a “Primetime” interview with Diane Sawyer in 2003 [Mega].
Despite wanting to move on from her high-profile romance, Britney was still pressed about the end of her relationship with Justin. In 2003, she sat down with Diane Sawyer for a Primetime interview, in which Diane questioned Britney about the breakup, seemingly indicating that Britney “did something” to cause the romance to end. “He has gone on television and pretty much said you broke his heart,” Diane said. “You did something that caused him so much pain, so much suffering — what did you do?”

Britney was noticeably shaken by the questions and began crying during the interview. The exchange was featured in the documentary Framing Britney Spears, causing Britney’s loyal fans to request Diane apologize to Britney for how she treated her in the interview. Fans have also rallied around the pop star, showing her support and some disdain for her former flame, Justin.

Britney & Justin’s Relationship Today

Britney and Justin today [AP].
In the years since their breakup, both Britney and Justin have gotten married, had kids, and more. Within the last year, Britney complimented Justin’s songwriting talents and the pair are seemingly on amicable terms. “Even though they aren’t going to be hanging out with each other anytime soon, they have no issues with each other,” a source shared EXCLUSIVELY with HollywoodLife in April 2020. “[They] would be more than happy to be in the same room as each other. They are very cool with each other.”

Justin was subject to his past criticism of Britney in Framing Britney Spears — particularly due to creating a narrative that she cheated on him via his song and video “Cry Me A River.” In response to fan comments, Justin issued a public apology to Britney. “I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn, or did not speak up for what was right,” Justin wrote on Instagram on February 12. “I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny…I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn, or did not speak up for what was right,“ he added.

The Justified singer once again spoke out in support of Britney after she spoke out in court against her on-going conservatorship. In her 24 minute testimony, Britney alleged that she was unable to have another child, was forced to tour in 2018, and put on drugs like lithium. “Regardless of our past, good and bad, and no matter how long ago it was… what’s happening to her is just not right,” Justin began via Twitter on June 23. “No woman should ever be restricted from making decisions about her own body,” he also said, making a direct reference to Britney’s claim that she is unable to remove an IUD that prevents pregnancy.

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