The Story Behind Justin Timberlake's Big Break Up With Britney Spears (While She Was Shooting A Music Video)

Singer Britney Spears and singer Justin Timberlake of N'Sync attend the 44th Annual Grammy Awards Pre-Party Hosted by Clive Davis on February 26, 2002 at Beverly Hills Hotel in Beverly Hills, California.
(Image credit: Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images/Getty Images)

It’s been over two decades since the huge breakup between the picture-perfect pop couple Britney Spears and Justin Timberlake, but there’s no denying the huge impact that three-year relationship had on each of their lives. In fact, the *NSYNC star seems to be a pretty significant part of Spears’ new memoir The Woman in Me, in which she revealed that she had an abortion after getting pregnant with Timberlake’s baby and opens up about the cheating that led to their split.

Those of us who grew up in the early aughts likely remember the allegations, the “Cry Me a River” music video and the backlash Britney Spears faced, but the singer’s memoir gives more details into what happened, and the director of the music video she was filming at the time has spoken out about the two-word breakup text Justin Timberlake allegedly sent her. Let’s take a look at the story behind Spears and Timberlake’s 2002 split.

Britney Spears in Lucky music video.

(Image credit: Vevo)

Britney Spears Recalls Being ‘Comatose’ After Justin Timberlake Broke Up With Her By Text 

It turns out that infidelity was involved in Justin Timberlake and Britney Spears’ breakup, as the pop star admitted in The Woman in Me (per Page Six) that she “made out with” choreographer Wade Robson one night, but that she and the boy-bander agreed to move past it. Maybe that’s partially why she was so “devastated” when he allegedly sent her a breakup text in February 2002 while she was in the middle of shooting a music video. 

Britney Spears was filming the video for “Overprotected: The Darkchild Remix,” and director Chris Applebaum recalled to Page Six that she went missing for 20 to 40 minutes during shooting. When he tracked her down, she was crying and showed him a text she’d reportedly received from Justin Timberlake that read: 

It’s over!!!

Chris Applebaum told her he understood if she didn’t have it in her to finish the video, but he encouraged her to stay and show Justin Timberlake that he’d “just made the biggest fucking mistake of his life.” The director said she responded by saying: 

You know that? That’s a good idea. I’m going to show him that he blew the best thing he ever had.

Britney Spears got through the video, but the period of time following the breakup was brutal, as she wrote in her memoir (via the New York Times): 

I was comatose in Louisiana, and he was happily running around Hollywood.

Despite reports that Justin Timberlake had also cheated on Britney Spears — which the “... Baby One More Time” singer seemingly confirmed in The Woman in Me — the *NSYNC member was painted as the victim in the breakup, thanks to his public comments and the release of his single “Cry Me a River.” 

Justin Timberlake in Cry Me a River video.

(Image credit: Vevo)

Justin Timberlake Said He Was ‘Scorned’ And ‘Pissed Off’ Following The Breakup 

In the months that followed their breakup, Justin Timberlake was promoting the release of his first solo album Justified, and of course he was often asked about Britney Spears. He told People (via EW) in June 2002 that it still hurt too bad to say the word “breakup,” after the magazine named him one of America’s Top 50 Bachelors, saying: 

You get to a point where you’re crying yourself to sleep at night. I feel like I’m in the middle of a soap opera. I honestly know what it’s like to have a broken heart now.

He also did an interview with Barbara Walters for 20/20, in which he said he’d promised Britney Spears he wouldn’t talk about the reasons for their split. When Walters asked him specifically if Spears had cheated on him, he replied: 

We're not perfect. I don't judge anybody. I think that it’s just a situation of, it's just young love. It was a very intense relationship, that's for sure.

The next year, however, he released the single “Cry Me a River” — a song about a man who’s moving on after being cheated on. In the music video, Justin Timberlake gets revenge on his ex — played by a Britney Spears look-alike — by breaking into her house and hooking up with another woman. In Timberlake’s 2018 book HIndsight: & All the Things I Can't See in Front of Me, he wrote (via US Weekly): 

I’ve been scorned. I’ve been pissed off. I wrote ‘Cry Me a River’ in two hours. I didn’t plan on writing it. The feelings I had were so strong that I had to write it, and I translated my feelings into a form where people could listen and, hopefully, relate to it. People heard me and they understood it because we’ve all been there.

Britney Spears addressed the media backlash she faced following the release of “Cry Me a River” in her memoir, saying Justin Timberlake had portrayed her as a “harlot.” 

britney spears in her slumber party video

(Image credit: RCA)

Britney Spears Faced Fallout In The Press After The Breakup And ‘Cry Me a River’ 

In The Woman in Me, Britney Spears wrote about Justin Timberlake’s breakup revenge video, describing it as, “a woman who looks like me, cheats on him and he wanders around sad in the rain,” saying that afterward she was then made out in the media to be a “harlot who’d broken the heart of America’s golden boy.” 

Britney Spears did not speak to the press much around that time, but has said she was made to do the now-infamous 2003 interview with Diane Sawyer, which has become widely criticized since the release of the 2021 documentary Framing Britney Spears. During the sit-down, the journalist made the 21-year-old cry with questions about Justin Timberlake like:  

You did something that caused him so much pain, so much suffering. What did you do?

When asked specifically if she’d betrayed her then-boyfriend, Britney 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.

Diane Sawyer also made comments about the singer's clothes and asked her if she had a shopping addiction. 

After Framing Britney Spears explored the unfair treatment Britney Spears faced following her split from the *NSYNC singer, Justin Timberlake issued a public apology to his ex-girlfriend and Janet Jackson — who shouldered the majority of the criticism following their 2004 Super Bowl halftime show “wardrobe malfunction” — admitting that he had “benefited from a system that condones misogyny and racism.”

The Woman in Me by Britney Spears is out now, with other revelations from the pop singer’s life including that she was nearly cast for the lead of The Notebook over Rachel McAdams and her complicated feelings about the “#FreeBritney” movement

Heidi Venable
Content Producer

Heidi Venable is a Content Producer for CinemaBlend, a mom of two and a hard-core '90s kid. She started freelancing for CinemaBlend in 2020 and officially came on board in 2021. Her job entails writing news stories and TV reactions from some of her favorite prime-time shows like Grey's Anatomy and The Bachelor. She graduated from Louisiana Tech University with a degree in Journalism and worked in the newspaper industry for almost two decades in multiple roles including Sports Editor, Page Designer and Online Editor. Unprovoked, will quote Friends in any situation. Thrives on New Orleans Saints football, The West Wing and taco trucks.