Here’s a truncated version of Justin and Britney’s relationship timeline. Both had been on TV since 1992, when they individually competed on Star Search. In 1993, they joined the cast of MMC (as did Ryan Gosling and Christina Aguilera). Justin has said that he “was infatuated with [Britney] from the moment [he] saw her,” and Britney has said that she had her first kiss with him around this time. Justin and Joshua “JC” Chasez, himself a Mouseketeer since 1990, would later make up two-fifths of *NSYNC, which released its self-titled debut album in 1997. Britney joined *NSYNC’s Second II None Tour as a supporting act in 1998, and released her own debut, …Baby One More Time, in 1999. By the end of 2000, *NSYNC was promoting its second and ultimately most successful studio album, No Strings Attached (2000); Britney was breaking records with her own sophomore effort, Oops!…I Did It Again (2000); and Justin and Britney were confirmed to be dating.

At the American Music Awards on January 8, 2001

Beyond their shared celebrity and work history, the pairing made a lot of sense. Both artists were from the South, were often described as perfectionists, and danced as well as they sang. Once they went public in 2000, they really went public: they openly had hokey nicknames for each other, appeared in matching denim-on-denim outfits at the American Music Awards, and flirted on stage during the Super Bowl halftime show. Britney practically beams in interviews about Justin from this time; there’s lots of talk about how seldom they get to see each other, how there’s nothing better than a movie night on the couch, and how she’d “love to be with him forever.”

Then, something happened in early 2002. It was rumoured to be an affair on Britney’s part, but — and I’ll continue to stress this — we the public don’t (and shouldn’t claim to) know the full story. Immediately after the breakup, *NSYNC went on hiatus and Justin went into the studio to record his first solo album, Justified (2002). It was finished in six weeks, with much of it produced by Timbaland and the Neptunes (aka Pharrell and Chad Hugo). The album’s debut single, “Like I Love You,” was released in August and peaked at #11 on the Billboard Hot 100 chart. For a star as big as Justin was, the song had underperformed. There wasn’t anything wrong with it, nor with its Diane Martel-directed video (even if Justin arguably didn’t need to wear a 7/11 graphic tee for his dance sequences in a 7/11 parking lot). The problem, as the BBC put it in their brutal coverage of the song’s chart performance, was Britney-related:

Justin Timberlake’s solo debut has failed to knock rapper Nelly from the top of the UK singles chart. The N’Sync singer’s Like I Love You was heavily tipped to shoot straight to the top of the charts. But the Michael Jackson-influenced track could not muster enough sales to beat Nelly’s worldwide hit Dilemma, which features Destiny’s Child singer Kelly Rowland. While N’Sync have achieved huge success in the US, in the UK Timberlake is best known as the former boyfriend of pop superstar Britney Spears.

Justin’s star persona had indeed been inextricably linked to Britney’s for a solid two years. She was the global superstar of the duo, the one that tabloids actually cared about at the time—in the sense that she sold lots and lots of magazines, that is.

With his mother, Lynn, on ABC’s “20/20” in early November, 2002

The album wasn’t set to be released in full until early November, which gave Justin a chance to course-correct. Ahead of its release, he spoke to Barbara Walters for a televised interview in his family home in Tennessee. “The impression is that Britney did something very bad that hurt you; she had a relationship with someone else. Was there an incident?” Walters asks Justin during the episode. “I promised to her that I wouldn’t say specifically why we broke up,” he responds, implying that such information was damning in some way. When Walters asks whether the two really kept their virginity pledge — Britney wore a purity ring throughout their relationship — he sarcastically responds, “Sure,” and then laughs. He’s otherwise careful to present himself as sensitive, someone for whom it all comes back to the music; that other stuff was just noise. (When Walters asks whether he’s seeing anyone new, he replies, “If you really want to know who my girlfriend is, it’s those 13 songs on that CD.”) An obvious effort has also been made to establish him as a mama’s boy. When Justin “cried himself to sleep” after the breakup, his mother, Lynn, cried with him. “It was tough for both of us ‘cause I can’t stand to see him hurt,” Lynn tells Walters, her eyes welling up with tears.

“What do you most want people to know about your son?” Walters asks her later in the interview.

“That he genuinely, deep down inside, is a good person.”

In less than ten minutes, Justin assumes the role of heartbroken wunderkind, and Britney the cheater who wasn’t as pure as she’d been telling everyone. If this was to be his new strategy, the fact that Britney’s brand had become increasingly risqué over the preceding couple of years would only work against her.