This article is taken from the April 2021 issue of The Critic. To get the full magazine why not subscribe? Right now we’re offering five issue for just £10.

Justin Timberlake is sorry for everything. He’s sorry about the 2004 Super Bowl half-time show, when he exposed Janet Jackson’s boob during a dance routine — a wardrobe malfunction that knocked her career into the doldrums for a decade after outraged moralists inveighed against her apparently autonomous tit, but which had no consequences for him.

He’s sorry how he treated Britney Spears, too. (Timberlake has been particularly criticised for his 2002 “Cry Me a River” video, which featured a lookalike of his ex-girlfriend Britney Spears, and left the audience in absolutely no doubt that the unfaithful girl in the song was her.) In an apology posted on Instagram, he wrote that he was sorry for all his “ignorance” and “privilege”.

As the person who actually did these things, it’s a bit of a reach to imagine he’s only recently become aware of them

The world noted this, considered it, and responded: Justin Timberlake, it was widely concluded, is too late. As the person who actually did these things, it’s a bit of a reach to imagine he’s only recently become aware of them. He’s had the best part of two decades to reflect on them, yet he only manages to choke out some self-reproach after the New York Times documentary Framing Britney Spears forced public attention back onto his actions? Unconvincing.

Many women are owed justice for their treatment in the noughties, a time when internet snark and mainstream prurience formed a crushing pincer movement from which few famous women could extricate themselves. Stars like Britney and Janet, who were held up for global humiliation, are being granted a second reputation: not the sluts they were mocked as, but victims of a misogynistic entertainment industry.

If we’re making victims, there will have to be new villains too, and Timberlake is in prime position to become one. This is largely, it must be admitted, because he acted pretty shabbily. The Super Bowl furore was overwhelming, but Timberlake was notably slack in offering support to his co-star (when she was disinvited from the Grammys, he could have withdrawn in solidarity, instead of showing up to collect his own awards).

The Britney case looks even bleaker. It’s all very well for him to say in his Instagram apology that he “[does] not want to ever benefit from others being pulled down again”, but his entire solo career is effectively founded on the moment he turned against her. The two got together as pop royalty when he was still a member of boyband ’N Sync — she was the horny virgin queen panting in school uniform, he was the clean-cut falsetto consort, and that was very definitely the order of seniority.

The two acts shared both a label (Jive) and a powerhouse songwriter/producer (Max Martin), and all this synergy was very good for launching ’N Sync on the world. But it was also — let’s be honest — a bit demeaning for Timberlake. When your girlfriend is the world’s most famous promise ring wearer, you’re not exactly burnishing your stud credentials.

For his solo launch, there would have to be a new Timberlake. A Timberlake who had sex, and didn’t maintain a gentlemanly silence about it. Throughout 2002, anyone who asked whether he made it with Britney got a smirking affirmation.

If you were there at the time, blaming him now feels good, because it’s better than remembering all the times you sang along with “Cry Me a River”

The rumours of Britney cheating were a gift to him, really. Working with RnB producers the Neptunes and Timbaland, Timberlake was reborn gritty. And here’s the thing: I loved it. Loved the gossip, loved the drama, loved the bad-boy stylings in the “Cry Me a River” video, where Timberlake sneaks around not-Britney’s mansion dressed like Tony Curtis in The Boston Strangler. If I felt bad for her, I could remind myself that they were labelmates, and surely Jive would have squashed this if she minded. It was all in the game.

I loved knowing that her song “Everytime” was probably an answer song, too: a pretty, plaintive ballad of apology with a video that shows Britney fleeing the press, then sinking into a bath and apparently drowning. Pure melodrama. All in the game.

Retrospectively, it feels like a cry for help from a woman who had been reduced to tears on TV by interviewers demanding to know why she so cruelly hurt Justin. It was fun to see Britney torn down, the perfect girl shown up as no better than she ought to be.

The focus on Timberlake as a bad agent conveniently forgets the machine behind him: a label that chose his rebrand over protecting her image, a public that was hungry for her fall. If you were there at the time, blaming him now feels good, because it’s better than remembering all the times you sang along with “Cry Me a River”.

You can still catch me booming out the seductive malevolence of its bridge: “Oh, the damage is done so I guess I’ll be leaving.” I don’t exactly feel bad that some of that damage has eventually found its way back to Timberlake, but all the same, a lot of the people who won’t accept his apology now are people who would do better to think about their own sorry.