Britney Spears Justin Timberlake Dating Timeline – Hollywood Life

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  • Britney Spears and Justin Timberlake dated from 1999 to 2002 during their early days of fame
  • After the split, he painted Britney as a cheater in interviews and his “Cry Me A River” video
  • Justin publicly apologized to Britney after her struggles were the subject of a 2021 documentary

Britney Spears and Justin Timberlake were pure pop royalty in the late ’90s and early aughts, so people’s obsession with their relationship comes as no surprise. The “Baby One More Time” singer, 40, and NSYNC frontman41, 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.

After the breakup, Justin mocked his ex in music videos and began openly talking trash about her, even as her mental health appeared to suffer. (“Cry Me A River” is honestly creepy in hindsight, and we all remember how he was Mr. Kiss-and-Tell in that TMI-packed 2002 Hot97 radio interview.)

Britney Spears, Justin Timberlake
Britney Spears and Justin Timberlake’s relationship is still talked about, despite the fact they split in 2002. (MEGA)

Both singers would move on romantically — Justin wed Jessica Biel40, in 2012 and Britney married actor Sam Asghari, 28, in 2022 — but the bitterness would remain. 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.

Britney & Justin Meet: 1992

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

The cast of ‘The All-New Mickey Mouse Club.’ Follow Favorite

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.”

Britney & Justin Start Dating: 1999

Justin and Britney started dating in 1999. (MEGA)

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, “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.”

Britney & Justin’s Iconic AMAs Looks: Jan. 2001

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.

Justin and Britney at the 2001 American Music Awards. (AP)

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 “regs” 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.

Britney & Justin Play The Super Bowl: Jan. 2021

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.

Justin and Britney performing with Aerosmith and more and the 2001 Super Bowl halftime show. (AP)

NSYNC joined rock band Aerosmith on stage for a medley, before Britney and a slew of stars (Mary J. Blige and Nellyamong 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.

Justin & Britney At The ‘Crossroads’ Premiere: Feb 2022

Britney and Justin at the premiere of ‘Crossroads’ in 2002. (AP)

In February 2002, Justin supported Britney at the premiere of her film Crossroadsco-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: Mar. 2002

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 the 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” lead to the split. Way to leave everyone hanging.

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

Justin Releases ‘Cry Me A River’: Dec. 2002

Justin released the song “Cry Me A River” at the end of 2002, seeming the lay bare his heartbreak following the Britney split. The drama only intensified after the music video dropped in Dec, featuring a Britney Spears look-alike and a strong suggestion that Miss Spear’s cheated.

Britney Releases ‘Everytime’: 2003

Britney appeared to respond to the track with her own ballad in 2003. “Everytime,” a single off of her album In The Zoneshowed off Britney’s more contemplative, soulful side.

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

Britney’s Diane Sawyer Interview: Nov. 2003

Despite wanting to move on from her high-profile romance, Britney was still pressed about the end of her relationship with Justin. She sat down with Diane Sawyer for a Primetime interview in Nov. 2003, where the journalist pushed Britney to admit what she “did” to end the romance.

Britney Spears sat down for a “Primetime” interview with Diane Sawyer in 2003. (MEGA)

“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 demand an apology from Diane. Britney called out the news anchor directly in a Dec. 2021 Instagram post. She slammed Diane for “forcing” her “to talk” and told the interviewer she could “kiss” the singer’s “white a**.”

Justin Writes Another Britney Song: 2006

Justin continued to talk about the Britney breakup in the mid-2000s. “I felt like she had a couple of opportunities to just sort of stick up for me, and she didn’t,” he complained to GQ in 2006. “Which is fine. But at that time, you know, I fought back, and that’s the way I fought back. I used my mind. I came up with a song.”

The comments seemed like a low blow at the time. While Justin was griping, Britney’s personal problems were rapidly escalating. Her marriage to Kevin Federline ended in Nov. 2006, mere weeks after they welcomed son Jayden in September 2006. In 2008 she was hospitalized on a 5150 hold, and a month later she was placed under her father Jamie Spears’ conservatorship.

Justin Says They Don’t Speak: 2011

Justin looked back on the relationship in a 2011 interview with Vanity Fair, admitting it’d been nearly a decade since they last spoke. “We were two birds of the feather — small-town kids, doing the same thing,” he told the magazine. “But then you become adults and the way you were as kids doesn’t make any sense. I won’t speak on her, but at least for me, I was a totally different person. I just don’t think we were normal; There was nothing normal about our existence.”

Britney & Justin Have ‘No Issues’: 2020

While Britney and Justin certainly weren’t besties, a source shed some EXCLUSIVE light on the state of their relationship in April 2020. “Even though they aren’t going to be hanging out with each other anytime soon, they have no issues with each other,” the insider shares. “[They] would be more than happy to be in the same room as each other. They are very cool with each other.”

Around the same time, Brit praised her ex for his musical skills on Instagram. She shared a clip of herself dancing to his song “Filthy,” and wrote, “PS I know we had one of the world’s biggest breakups 20 years ago…… but hey the man is a genius. Great song JT!”

Justin Apologizes To Britney: Feb. 2021

After years out of the spotlight, the songstress was the center of conversation once again after the release of the documentary Framing Britney Spears in early 2021. The doc unpacked Britney’s place in pop culture, while also taking aim at some of her harshest critics during the 2000s — namely Justin.

The “Bye, Bye, Bye!” singer was basically forced to issue a public apology to Britney in Feb. 2021. In it, he wrote that he was “deeply sorry for the times in my life where my actions contributed to the problem.”

He continued, apologizing for times “Where I spoke out of turn, or did not speak up for what was right.” Justin added, “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 contributed actions to the problem, where I spoke out of turn , or did not speak up for what was right.”

Justin Supports Britney’s Conservatorship Fight: Jun. 2021

The Justified singer once again spoke out in support of Britney after she spoke out in court against her ongoing conservatorship in summer 2021. In her 24-minute June testimony, Britney accused her conservators of forcing her to take strong psychiatric drugs like Lithium and refusing to let her have her IUD removed so she could try to have another child.

Justin took to Twitter to defend his ex in a June 23 post, that said, “Regardless of our past, good and bad, and no matter how long ago it was… what’s happening to her is just not right.” Regarding her wishes to have a baby, he added that, “No woman should ever be restricted from making decisions about her own body.”

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