It’s been a struggle to feel sympathy toward young Justin Timberlake since the release of the Britney Spears documentary in 2021. The tables began turning against Spears’s ex when Framing Britney Spears viewers found Timberlake contributed to her unfair portrayal in the media. Though the New York Times documentary covers a large swath of time from Spears’s rise from pop star to suffocating fame to her troubling conservatorship, it spends a considerable amount of screentime diving into exactly how Timberlake weaponized a narrative to make himself a victim and Britney the slut following their breakup. After the documentary dropped, Justin attempted to quell backlash with a statement lazily addressed not only to Spears but also to Janet Jackson as well. We guess killing two birds with one notes app apology was too convenient to pass up. “I benefitted from a system that condones misogyny and racism,” he wrote at the time. Spears’s new memoir, The Woman in Me, doesn’t make him look much better. In fact, he looks worse.
“I don’t know if when you’re younger love’s a different thing, but what Justin and I had was special,” Spears writes. “He wouldn’t even have to say anything or do anything for me to feel close to him.” Timberlake ended their three-year relationship by text message in 2002. A source told Entertainment Tonight that Timberlake is “focusing on his own family” and trying to “grow and evolve instead of bringing up the past.” That being said, several sources spilled that Timberlake was “concerned” about the book’s release, according to a “Page Six” report. Here’s a few reasons why he may want to leave the past in the past.
A Janet Jackson song soundtracked their first kiss
They shared their first kiss at a Mickey Mouse Club cast sleepover: “We played a game of Truth or Dare, and someone dared Justin to kiss me,” Spears writes. “A Janet Jackson song was playing in the background as he leaned in and kissed me.”
After “… Baby One More Time” made Spears a star in 1998, Spears and Timberlake reconnected on their joint tour. “Pretty soon I realized that I was head over heels in love with him,” she writes. “So in love with him it was pathetic.” Eventually, they lived together in Orlando. “I was so happy.”
She had to put up with Justin’s AAVE
“NSYNC was what people back then called ‘so pimp.’ They were white boys, but they loved hip-hop,” Spears remembers. “NSYNC hung out with Black artists. Sometimes I thought they tried too hard to fit in.” She then gives an example of Justin doing the absolute most when they ran into “a guy with a huge, blinged-out medallion” on the streets of New York early in their relationship. “J got all excited and said, so loud, ‘Oh yeah, fo shiz, fo shiz! Ginuwiiiiiine! What’s up, homie?’” Spears’s longtime friend and assistant, Felicia Culotta, mocked him, but “J wasn’t even embarrassed. He just took it and looked at her like, Okay, fuck you, Fe.” He was embarrassing her from the beginning, I fear.
According to the memoir, this was the same trip that Justin acquired a chain with the letter T on it, which is likely the same gaudy, diamond-encrusted necklace he wore constantly around during the late ’90s and early 2000s. He even famously wore it at the 2001 American Music Awards — the same event he and Spears gagged everyone with their matching denim outfits (which Spears said was her idea).
Spears “couldn’t help but notice” when press treated her and Timberlake differently
“I had a hard time being as carefree as he seemed,” she recalls those early years of her relationship with Timberlake. “I couldn’t help but notice that the questions he got asked by talk show hosts were different from the ones they asked me. Everyone kept making strange comments about my breasts, wanting to know whether or not I’d had plastic surgery.”
Timberlake sounded like a serial cheater
Spears writes that he cheated “a couple of times,” but she always turned a blind eye. Though Spears did kiss Wade Robson once at a party and admitted it, it was nothing compared to her boyfriend’s activities. “Especially because I was so infatuated and so in love, I let it go, even though the tabloids seemed determined to rub my face in it,” she writes. “When NSYNC went to London in 2000, photographers caught him with one of the girls from All Saints in a car. But I never said anything.” Another time in Vegas, Justin cheated with a famous woman whom Britney doesn’t identify because she’s married with kids. “I don’t want her to feel bad.”
Timberlake thought playing guitar would ease Spears’s pain during their abortion
While Spears was writhing in pain on the bathroom floor, her boyfriend had a genius idea. “Justin came into the bathroom and lay on the floor with me,” she remembers in her memoir. “At some point, he thought maybe music would help, so he got his guitar and he lay there with me, strumming it.”
He broke up with Spears over text message
In Spears’s retelling, Timberlake became “very standoffish” while working on his debut solo album, Justified for reasons that would become clear when she heard the album. “I think that was because he’d decided to use me as ammunition for his record, and so it made it awkward for him to be around me staring at him with all that affection and devotion,” she speculates. “Ultimately, he ended our relationship by text message while I was on the set for the video for the ‘Overprotected’ remix by Darkchild.” She had go back out and dance after receiving the message in between takes. Justin Timberlake, a pioneer of the text message breakup. Mind you, it is 2002.
“When he left me I was devastated,” Spears writes. She was barely able to “speak for months” and “could only cry” when anyone asked her about him. “I don’t know if I was clinically in shock, but it felt that way.”
Timberlake turned up at her doorstep with a framed breakup letter. Britney still keeps it under her bed.
While Spears was holed up in Louisiana to recover from the breakup, Timberlake flew out to visit. He brought her a long letter that she still has under her bed. “At the end it said — it makes me want to cry to think about it — ‘I can’t breathe without you.’ Those are the last words in it,” she writes. “It almost felt like I was suffocating, like I couldn’t breathe, after all that had happened. The thing is, though, even after I saw him and read the letter, I didn’t come out of the trance.”
Timberlake slept “with six or seven girls” after the split
He grieved the relationship by … doing exactly what he did when he and Britney dated. “Justin ended up sleeping with six or seven girls in the weeks after we officially broke up — or so I heard,” she writes. “I understood the infatuation people had with him.”
Spears liked that Timberelake discussed their sex life in public. What she didn’t like was being portrayed as the “harlot.”
“Was I mad at being ‘outed’ by him as sexually active? No,” she writes. “To be honest with you, I liked that Justin said that. Why did my managers work so hard to claim I was some kind of young-girl virgin even into my twenties? Whose business was it if I’d had sex or not?” It was her negative depiction in “Cry Me a River” and the media that was troubling. “I was described as a harlot who’d broken the heart of America’s golden boy. The truth: I was comatose in Louisiana, and he was happily running around Hollywood.” Worse, he used a false narrative to give his album purpose: “shit-talking an unfaithful woman.”
Timberlake has a lot to be concerned about indeed. Could a second notes app apology be imminent?
