This article is taken from the March 2024 issue of The Critic. To get the full magazine why not subscribe? Right now we’re offering five issues for just £10.

If you ever doubt that celebrity is a kind of hell, imagine this: you’re 43, and you’re still defined by a relationship that started in your teens and ended when you were 21. Justin Timberlake is a multi-platinum selling artist. He’s been married to the actress Jessica Biel since 2012, and the couple have two sons. None of that matters because the only identity Timberlake is allowed to have is “Britney’s ex”.

This is partly his own fault. When Timberlake left the boyband NSYNC in 2002, he launched his solo career off the back of his break-up with Spears. Rumours that she had cheated on him gave him an alibi for graphically kissing and telling on America’s most famous alleged virgin.

An interview with him from the time was trailed with the unimprovably crass cover line: “Can we ever forgive Justin Timberlake for all that sissy music? Hey … at least he got in Britney’s pants.”

It was the classic double standard. Spears got slutshamed; Timberlake was the stud. Her life spiralled bleakly until she ended up under a conservatorship controlled by her father; his continued breezily.

He was a regular guest on Saturday Night Live, charming his way through filthy comedy songs. He took up acting. And he was a legit music star, merging pop with R’n’B to critical and commercial success.

But spears got her revenge. When her autobiography The Woman in Me came out last year, the most anticipated revelations were the ones about Timberlake, and she didn’t disappoint. Yes, she’d cheated on him — but he’d cheated on her more. When she’d got pregnant, she wanted to have the baby — he’d wanted her to have an abortion, and in the end she did so.

If saying sorry is never enough, why not become the monster you’ve already been judged to be?

The most damaging part wasn’t that he came out looking like a cad (it’s worth remembering that both were no older than 20 when all this happened). It’s that, in Britney’s telling, he came out looking cringe. A stupid white boy who greeted the black rapper Ginuwine with “fo’ shiz fo’ shiz … What’s up homie?” (Ginuwine didn’t recall the incident). A parody of the “sensitive” man who strummed his guitar while she suffered through the painful aftermath of the abortion.

Part of the reason Timberlake avoided the usual boybander-to-obscurity pipeline was that he seemed to understand who he was meant to be. The noughties liked its popstars a little bit dirty, a little bit dangerous, ready to play along with the gossip culture, and he joined in adeptly. It feels appropriate that one of his best songs is the ballad “Mirrors”: he’s a screen for reflecting back other people’s desires.

What is wanted now, though, seems harder for him to deliver. In the great morality play of celebrity watching, the only role being offered to him is that of villain. There’s a vacancy for a bad guy who can carry the can for everything the entertainment industry got wrong when it comes to women like Spears, and Timberlake is perfectly placed to fill it.

That’s not only because of his part in Spears’s story, but also because he was integral to the Superbowl performance 20 years ago that ended with Janet Jackson’s breast exposed — at great cost to her career, and no cost to his. None of his apologies (there have been several, going back to at least 2006) seem to have shaken his position as the world’s premier exemplar of blithe white male privilege.

Commentary on him seems driven by a desire to see him fail. Critics declared his Americana-tinged 2018 album Man of the Woods a “retreat into whiteness” (even though he was working with the same black production team who’d been with him since his debut Justified). A recent SNL spot had “an air of desperation”, decided one reviewer. There was unmistakable glee when Spears fans organised to ensure his new single “Selfish” was beaten in the charts by a Spears song of the same name.

Spears herself offered an olive branch, praising his track on her Instagram and apologising to anyone she “offended” with her memoir. Timberlake opted not to take it. At a recent performance, he introduced his song “Cry Me a River” (written in response to the break-up with Spears) by saying: “I’d like to apologise to absolutely fucking nobody.”

Obviously it’s undignified to be publicly rucking with your teenage ex in middle age, but plenty of pop stars run their careers very successfully on beef. As I write, the rappers Megan Thee Stallion and Nicki Minaj have been engaged in a mutually beneficial feud, pushing both their (underwhelming) new singles up the charts.

The issue is whether Timberlake can pull off the heel turn. At the very least, he needs an edgier musical direction. Yet it’s hard to see what other option he has. Timberlake is caught in the pincers of the cancellee’s dilemma.

If saying sorry is never enough, why not become the monster you’ve already been judged to be? There’s a kind of relief in just giving up the fight for your innocence and embracing outlaw status. But there’s a cost too: if Timberlake commits to his antihero era, he’ll be letting the people who like him the least author his image. Celebrity truly is a kind of hell.