Britney Spears and Justin Timberlake were pure pop royalty in the late ’90s and early 2000s, so it’s no wonder the world was obsessed with their relationship. The “Baby One More Time” singer and NSYNC frontman seemed like they were perfect for each other when they went public in 1999. It was all cute soundbites and PDA-packed red carpet appearances until things came crashing down in 2002, amid rumors of cheating and lies.

Following the split, Justin appeared to shade Britney in his “Cry Me a River” music video and made eyebrow-raising comments about their relationship in interviews, fueling public scrutiny toward Britney just as she was grappling with mental health struggles.

Over the years, both moved on — Justin married actress Jessica Biel  in 2012, while Britney wed dancer Kevin Federline in 2004 (they divorced in 2007) and later married actor Sam Asghari in 2022 before their 2023 separation. Still, their shared history has remained a major talking point, especially after Britney’s 2023 memoir The Woman in Me revealed new details about their relationship, including claims that Justin cheated and that she had an abortion during their time together. It took nearly two decades for the “SexyBack” singer to finally apologize to his ex, seemingly prompted by a surge of support for the star amid her 2020s-era conservatorship battle.

So is everything good between Britney and Justin now? Take a look back at the exes’ romance and where their relationship stands now in our timeline, right here.

Key Highlights

• Relationship Overview: Britney Spears and Justin Timberlake were a pop culture phenomenon during the late ’90s and early 2000s.
• Public Split: Their breakup in 2002 was marked by public scrutiny and media speculation.
• Recent Developments: Britney’s memoir revealed new insights into their past relationship dynamics.
• Apologies Issued: Justin Timberlake publicly apologized to Britney years after their split.

When Did Britney & Justin First Meet?

Britney and Justin were both cast in The All-New Mickey Mouse Club back in 1992. At the time, Britney and Justin were both around 11 years old. The show also featured future stars Christina Aguilera and Ryan Gosling and ran from 1993 to 1996.

Following the series, Britney returned to Mississippi. She eventually came back to New York City to pursue her singing career, however. Justin, meanwhile, was recruited as a member of the boy band NSYNC.

Though they parted ways, the songstress seemed to have left an impression on Justin. He told GQ in 2006, “I was in love with her from the start. I was infatuated with her from the moment I saw her.”

When Did Britney & Justin Start Dating?

Fame eventually reunited Britney and Justin eventually, who began dating in 1999 as both of their careers began taking off. Talking about their connection with The Observer in 2001, Britney said, “We’ve gone through so much together and we’ve known each other since we were 12 years old. We know each other inside and out.”

What Were Their Iconic Looks at the AMAs?

As their relationship progressed, Justin and Britney became red carpet regulars. One of the couple’s most iconic moments came at the 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 2021 interview with The Hollywood Reporter, Justin admitted he had some fashion “regrets” from his early years. “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 back in Aug. 2020.

When Did They Perform at The Super Bowl?

With both stars at the top of their game, it was only a matter of time before they shared a massive stage. Fans of Britney and Justin were treated to a joint performance by the pair at the Super Bowl XXXV halftime show on Jan. 28, 2001.

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, solidifying both stars’ place in pop history.

What Happened at The ‘Crossroads’ Premiere?

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 they would make together before they went their separate ways.

When Did They Break Up?

Britney and Justin’s relationship ended in early 2002, but the couple didn’t immediately publicize the split. The “Overprotected” singer was the first to break the news during an appearance on Britain’s “Big Breakfast” in Mar. 2002, as reported by CNN. “I would not say I was in an intense relationship with anyone at the moment,” she dished at that time. “I’m single right now.”

The tabloids hounded the exes about the breakup for months after during which time Justin began to shape his side of the story. He told Barbara Walters in a Nov. 2002 ABC interview, “I remember when we decided we were going to go our separate ways; we sat down and I said to her, ‘If there’s ever a moment where you ever need me, you can rest assured that I will be there because I love you as a person and I will always love you.” Sparking even more gossip, he told Barbara he “promised” Britney he wouldn’t share what “specifically” led to the split. Way to leave everyone hanging.

Though he tried to play the good guy most of the time, Justin also tried to shame Britney by sharing lurid details about their sex life together. One of the most infamous instances was during an appearance on The Star & Buc Wild Morning Show in Nov. 2002 where he admitted to sleeping with Britney despite both publicly pledging to stay virgins until marriage.

What Was The Impact of ‘Cry Me A River’?

Justin released the song “Cry Me A River” at the end of 2002, seemingly laying bare his heartbreak following his split from Britney. The drama only intensified after the music video dropped in Dec., featuring a Britney Spears look-alike and strongly suggesting that Miss Spears had cheated.

Did Britney Respond With ‘Everytime’?

Britney appeared to respond to Justin’s track with her own ballad in 2003 titled “Everytime,” which showcased her more contemplative side off her album In The Zone.

The singer has never confirmed or denied that this song is about her former flame; however fans still read into lyrics like “Why are we strangers / When our love is strong?” as being about Justin.

What Happened During The Diane Sawyer Interview?

Despite wanting to move on from her high-profile romance, Britney was still pressed about its end during an interview with Diane Sawyer. In Nov. 2003 she sat down for a Primetime interview where Sawyer pushed her to admit what she “did” to end things with Justin.

“He has gone on television and pretty much said you broke his heart,” Diane said. “You did something that caused him so much pain — what did you do?” Britney was noticeably shaken by these questions and began crying during this interview.

This exchange was featured in the documentary Framing Britney Spears, causing her loyal fans to demand an apology from Diane Sawyer directly after it aired. In Dec. 2021, Britney called out Sawyer on Instagram for “forcing” her “to talk,” telling her she could “kiss” her “white ass.”

Diane Sawyer Interview Aftermath: What Did Justin Say?

Justin continued discussing his breakup with Britney throughout mid-decade interviews as well; he mentioned feeling disappointed that she didn’t defend him publicly during this period when he felt attacked by media narratives surrounding them both.

Diane Sawyer Interview Aftermath: What Did Britney Go Through?

While Justin aired grievances publicly during interviews regarding his breakup with Britney Spears; she faced escalating personal issues including divorce from Kevin Federline shortly after welcoming their son Jayden.

Diane Sawyer Interview Aftermath: What Did They Say About Each Other?

In retrospective interviews from nearly ten years later (2011), Justin reflected upon how different they had become as adults compared to when they were young stars navigating fame together.

Diane Sawyer Interview Aftermath: What Is Their Current Relationship?

While it seems that neither are close friends today; sources indicated that they have no issues with each other as recently as April 2020 according to reports shared by HollywoodLife.

Around this time frame Brit praised him publicly for his musical talent via social media while dancing along to one of his songs titled “Filthy”. She expressed admiration stating how talented he is despite their past relationship struggles.

Diane Sawyer Interview Aftermath: What Did He Apologize For?

After years away from media scrutiny following her conservatorship battle beginning early 2021; discussions resurfaced regarding how she had been treated by media outlets including those involving Justin Timberlake throughout their breakup period.

In February 2021 he issued an apology acknowledging how his actions contributed negatively towards situations involving women including those surrounding Brittany’s experiences during their relationship stating he regretted not supporting her better during difficult times.

Diane Sawyer Interview Aftermath: What Did He Support Her On?

Following further developments regarding Brittany’s conservatorship situation later that summer where she spoke out against being forced into taking medication without consent or being prevented from making personal choices regarding family planning options like pregnancy;

Justin took to social media expressing support towards Brittany stating no woman should be restricted from making decisions concerning her body regardless of past relationships or circumstances surrounding them both individually over time since breaking up years prior.

Diane Sawyer Interview Aftermath: What Did Brittany Reveal Recently?

In October 2023 Brittany revealed shocking details within her memoir discussing having undergone an abortion while dating him which shocked many fans who followed them closely throughout these events unfolding over decades since first meeting each other back then!

“It was unexpected but not tragic,” Brittany wrote reflecting upon how much love existed between them despite challenges faced along way throughout journey together leading up until eventual breakup occurring later down line.”