Britney Spears and Justin Timberlake were like the Canadian-tuxedoed prom queen and king of the early 2000s. In addition to the matching outfits, the pop stars had a cute backstory, family approval, silly nicknames and Hollywood good looks.
But they were no ordinary teens in love. There was a blinding spotlight on their relationship, which began in 1999 — when she was 17 and he was 18 — and ended in 2002. That’s because Spears really burst onto the pop scene. Her debut album “…Baby One More Time” was a megahit — going on to sell more than 25 million copies worldwide — and she was being hailed as “Madonna’s heir apparent.”
It sounds strange now, but there also was a complete public fixation on her virginity, which she was asked about in interviews as a minor — when reporters weren’t asking questions about her breasts. At 18, she was made to publicly respond to an “infatuated American businessman” making an $11 million “indecent proposal” to take her virginity, as was being blamed for being a bad influence on millions of young girls.
For Timberlake, his high-profile relationship with Spears helped establish his own star power. He had been a talented member of boy band NSync, but broke out as a solo artist, which isn’t an easy transition and many fail doing. He was pulled into the virginity narrative too, though in a backslapping way. Later after they split, he infamously made crude comments about having sex with her in interviews. He also implied she cheated in his revenge song, “Cry Me a River.” That set off a public back-and-forth between them and later, an apology, from him to her, 20 years later.
With Spears’s new memoir, The Woman in Me, out Oct. 24, correcting the record on that past relationship, we look back at how things played out at the time…
1992: They meet making TV’s The Mickey Mouse Club.
In her book, she writes that they shared a kiss during a game of Truth or Dare while a Janet Jackson song played. He told GQ in 2006, “I was in love with her from the start.”
1998: Spears opens for NSync
Timberlake’s boy band, NSync, goes on its second tour and Spears, with her new debut single “…Baby One More Time,” opens for them.
1999: Spears and Timberlake start dating
There are tons of rumors that they’re dating. She plays coy to Rolling Stone when asked if she’s seeing Timberlake or his bandmate Lance Bass, saying, “Overseas they say it’s Nick Carter of Backstreet Boys. I have no feelings at all.”
2000: Spears and Timberlake make their red carpet debut
They confirm they’re a thing and make their couple debut at the MTV VMAs in September. His mom, giving her stamp of approval, sits with them during the show. Brit later says JT asked her out prior to the release of her debut album,”…Baby One More Time,” which was in January 1999. Her album is a massive success and she embarks on her “(You Drive Me) Crazy Tour.”
2001: The “Pinky and Stinky” era
The pop pair becomes a golden couple of that era — and they lean in. They make adorable public appearances, including at an NSync charity basketball game with their nicknames for one another on their jerseys. As for the pet name, she later says, “I have a ring that he gave me that I wear on my pinky so he started calling me Pinky, and then I started calling him Stinky for some reason.”
They perform together, with headliner Aerosmith, during the Super Bowl halftime show, and wear their famous all-denim outfits to the American Music Awards. By the end of the year, they’re living together with Spears saying, “I’m not ashamed at all to say that I love him from the bottom of my heart… 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.”
In Spears’s memoir, she reveals that it was during the time, when she was 19, that they became pregnant and had an abortion. She says she would have had the baby, but Timberlake didn’t want to become a young dad.
2002: At a romantic Crossroads, they split
Her tremendous success makes her a hot commodity and she appears in the film Crossroads. In her book, she writes that the experience “wasn’t easy” because she was Method acting and didn’t know how to break out of my character. While Timberlake accompanies her to the premiere, makes a cameo when she hosts Saturday Night Live and they go to the Grammy Awards together, by March they split.
She tells the press the split is “amicable” and it’s because they’re “climbing two different mountains.” However, he paints himself as the wounded party, saying it “hurts” and he’s been “crying [myself] to sleep every 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.”
He gives multiple radio interviews talking about having sex with Spears. Ahead of the release of his solo album, he has a sit-down with Barbara Walters, and doesn’t deny it when Walters asks if Spears cheated on him. “We’re not perfect,” he says. “I don’t judge anybody. It’s just young love… It was a very intense relationship.”
He debuts his post-breakup song “Cry Me a River,” which is seemingly about their relationship, and hires a Spears lookalike to appear in it. Spears is asked about the video by MTV and says, “Boys will be boys,” but rocks a “Dump him” shirt in London as he moves on with Alyssa Milano. Timberlake gives an interview to Details magazine in which he criticizes Britney’s role in Crossroads, saying, “If she had a clue, she wouldn’t have made [it].” The tabloids declare they are at “war.”
2003: Spears calls out Timberlake for being “so exploitative”
Spears confirms — after Timberlake’s comments about their sex life — that they slept together. “I’ve only slept with one person my whole life. It was two years into my relationship with Justin, and 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,” she says to W.
She tells Elle U.K., “It was hard for me that he was so exploitative. Every interview that he did, he was just talking about us in such an open way and I just felt, ‘Is nothing sacred anymore?’ It was weird. It was … disappointing.”
She does her own big TV interview with Diane Sawyer, and the journalist paints her as the villain and asks why she broke Timberlake’s heart. She’s also asked if she “betrayed” the relationship and answers, “I’m not technically saying he’s wrong, but I’m not technically saying he’s right either. It was a really weird time … I just felt exploited and weird.” Spears later slams Sawyer for making her cry, and claimed her father forced her to do the interview.
2004: Spears releases “Everytime” video
“It’s about heartbreak, it’s about your first love, your first true love,” she tells MTV. “That’s something all people can relate to, because you all have that first love that you think you’re going to be with the rest of your life.” However, now that she’s revealed her abortion, fans have been looking at the video in a new light. It includes one woman giving birth while another is dying. In her memoir, she says, “To this day, [the abortion was] one of the most agonizing things I have ever experienced in my life.”
2006: Timberlake criticizes Spears’s handling of their breakup
“I felt like she had a couple of opportunities to just sort of stick up for me, and she didn’t,” he tells Details. “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.” Nonetheless, he claims he wants “to see her win.”
2007: As Spears struggles publicly, Timberlake says he has “no ill will”
In the years after their split, she looks for love and stability — marrying twice and having her two sons between 2004 and 2007. After her divorce from Kevin Federline, she tries to find her footing as a pop star and single mom in the fishbowl that was Hollywood in that era. Every stumble is documented by the tabloids. In her book, she says she started to rebel and act out due to the pressure and scrutiny, infamously shaving her head. In an interview with Oprah Winfrey, Timberlake — whose solo career continued to boom — says of his ex, “There’s no ill will. I have nothing but love for her … She has a huge heart and she’s a great person.”
2008: Spears is put in a conservatorship
2018: Timberlake says he wrote “Cry Me a River” after being “scorned”
As Spears is made to continue performing and has no control over her finances or personal decisions, Timberlake writes in his book, Hindsight: & All the Things I Can’t See in Front of Me, “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.”
2020: Spears reflects on their split, calling it “one of the world’s biggest breakups”
Spears posts one of her famous dancing videos to social media using Timberlake’s song, “Filthy.” She writes, “I know we had one of the world’s biggest breakups 20 years ago…. but hey the man is a genius!!!!”
In a podcast interview with Lance Bass, Timberlake is asked about the his and hers denim looks he and Britney rocked when they were a pair. “You do a lot of things when you’re young and in love,” he says.
2021: Timberlake issues an apology to Spears
As the #FreeBritney movement grows, the New York Times documentary Framing Britney Spears looks at her conservatorship as well as the events leading to it. It includes the relentless reporting on her virginity, comments by reporters about her body, Timberlake’s comments about their sex life as well as her struggles amid the media glare. Timberlake doesn’t come off well in the doc and there are calls on social media for him to apologize. Shortly after, he does, and also apologizes to Janet Jackson, who he let take the fall for the Super Bowl wardrobe malfunction.
Timberlake, who is now married to Jessica Biel with two kids, writes in part, “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.”
Later that year, Spears breaks her silence about the conservatorship in moving testimony alleging conservatorship abuse. Timberlake posts a message of support on social media: “After what we saw today, we should all be supporting Britney at this time… No woman should ever be restricted from making decisions about her own body.”
In November, her conservatorship ends after 13 years.
2023: Spears’s tell-all book reveals abortion with Justin — and more
After the conservatorship ends, Spears writes a book and the first excerpts appear online. She reveals that she and Timberlake became pregnant, reportedly when she was 19, and he urged her to have an abortion, which she did. She claims that while she did cheat on him, sharing one kiss with Wade Robson, Timberlake cheated on her more than once, including a famous actress she declined to identify.
Additionally, she claims she lost her virginity years before the pair dated. In ninth grade, she slept with her brother’s friend, who was a 17-year-old high school senior. Timberlake doesn’t comment, but a source close to the singer tells Entertainment Tonight he’s focused on his own family and “trying not to concern himself with Britney’s memoir.”
The Woman in Me comes out Oct. 24.
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