Britney Spears and Justin Timberlake were the golden couple of the late ‘90s and early 2000s for good reason. At one point, in the thick of their romance, Spears literally said, “He’s everything” about Timberlake. (Don’t worry, he gushed about her plenty, too.) Unfortunately, things didn’t end quite so happily between the two of them. After the couple announced their breakup in March 2002, they quickly transitioned from being lovey-dovey to downright shady. Looking back at Spears and Timberlake’s relationship timeline is super sad. (So yes, you’re going to want to locate your nearest box of tissues.)
In the fall of 2002, the once couple started trading a series of public barbs that are hard to see — Timberlake’s comments, in particular, were cutting. Post-breakup, the NSYNC frontman decided to publicize the intimate details of his sex life with Spears. It was... not a good look, especially considering that up until that point, Spears has publicly refused to comment on those aspects of their relationship
and said that she planned to wait until sex for marriage.
So how did these former lovebirds get to that point — and where do they stand now? Spears and Timberlake’s relationship is a bit of a doozy, but here are the highlights (and lowest lows).
1999: They Confirmed Their Romance
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Spears and Timberlake first met while filming
The Mickey Mouse Club in 1992, but they didn’t actually confirm their romance until 1999. Their relationship was a long time coming, though, especially if you ask JT.
Us Weekly, 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.” Nothing like falling for your childhood crush!
January 2001: They Sported Double Denim
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In what might be the most iconic JT-Britney moment, the
two wore matching all-denim outfits to the American Music Awards in 2001. And although this photo op has become the source of infinite Halloween costume inspo for couples everywhere, Timberlake kind of wishes everyone could forget about it.
“I confess that there was maybe a period in the '90s where I could skip over some of the outfits that were public, but the internet will never,” he told
The Hollywood Reporter in Feb. 2021.
September 2001: They Started Living Together
During an interview with The Guardian in 2001, Spears said that their relationship was getting very serious, explaining that
Timberlake “lives at her house with her when he's in LA.”
She added at the time, “I'm not ashamed at all to say that I love him from the bottom of my heart. As far as love is concerned, with him, too much is not enough.” Aw!
March 2002: They Broke Up
Spears and Timberlake shocked fans when
they broke up in March 2002, and they were interviewed about it repeatedly in the months following. In Nov. 2002, Timberlake revealed some details of their painful split to Barbara Walters. "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,’” he said, per Us Weekly. He also “promised her that [he] wouldn't say specifically why [they] broke up."
Sounds pretty good, but he
also laughed when Walters asked about their sex life, so there’s that. Despite Timberlake's words, the breakup was still tough for Spears to swallow. In Dec. 2021, the “Toxic” singer opened up about her post-breakup emotions in a since-deleted Instagram. “Something I never shared when I had that big breakup years ago was that I couldn't talk afterwards. I never spoke to anyone for a very long time,” she wrote.
September 2002: He Opened Up About Their Sex Life
During an interview with
The Star & Buc Wild Morning Show, Timberlake was asked, “ Did you f*ck Britney Spears?” It was a loaded question, considering how publicly Spears had spoken about wanting to wait to have sex until after marriage. Still, that didn’t stop Timberlake from answering (even if it should have). “Oh man,” he responded. “OK, I did it!” (Gross.)
November 2002: Timberlake’s “Cry Me A River” Music Video
Despite what Timberlake said to Walters about staying mum on the reasons behind their split, he didn’t keep to his word. That same month, he released his “Cry Me A River” music video, which told a very different story of their breakup and pointed the blame squarely in Spears’ direction. To make the message crystal-clear, he cast a Spears lookalike to play the role of his cheating ex-girlfriend.
July 2003: Britney Responded To Timberlake’s Comments
In an interview with
W Magazine, Spears responded to Timberlake’s comments — and she was (understandably) not happy about them. ”I’ve only slept with one person my whole life,” she explained at the time, per Entertainment Weekly, adding that she did wait ”two years into [her] relationship with Justin” to have sex.
She explained her disappointment with Timberlake’s comments, “I thought he was the one. But I was wrong! I didn’t think he was gonna go on Barbara Walters and sell me out.” Oof.
February 2021: Justin (Finally) Apologized
Framing Britney documentary, which highlighted Timberlake’s less than flattering comments, the actor received plenty of feedback. On Feb. 12, he responded to the criticism by finally apologizing to Spears, as well as Janet Jackson.
“I've seen the messages, tags, comments, and concerns and I want to respond. 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. I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism," he wrote on Instagram. “I specifically want to apologize to Britney Spears and Janet Jackson both individually because I care for and respect these women and I know I failed.”
August 2021: Britney Quoted Justin
Spears didn’t respond to Timberlake’s apology — at least, not publicly. But she did reference her ex in an Instagram caption in August 2021, writing, “
As JT would say ... haters gonna say it’s fake !!!!!” (The picture was a photo of a large cat though, so there doesn’t seem to be any hidden meaning to her post.)
Maybe she’s really just letting bygones be bygones?
Of course, Spears and Timberlake are happily in separate relationships now — Spears got engaged to Sam Asghari in 2021 and Timberlake has been married to Jessica Biel since 2012. I’m happy (see: relieved) to see that they seem to be getting along now.
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