Justin Timberlake may be in pop culture exile, but we shouldn’t gloat about his arrest

The one-time pop behemoth is stranded between the success of early superstardom and the arrival of nostalgic, late-in-life reappraisal, writes Adam White. But as he faces a legal crisis and a possible charge for driving while intoxicated, we should try and ease up on the jokes

Pale and mortified: Timberlake’s mugshot following his arrest (Getty)

The police officer didn’t know who Justin Timberlake was. That was probably the worst part of it. When the beleaguered pop star was pulled over by traffic cops in the Hamptons yesterday – he now faces a charge of driving while intoxicated – the arresting officer allegedly didn’t recognise him. Not even when he worried about its effect on his current world tour. “What tour?” the officer asked.

Whether much of this happened is unclear, credited only to “sources” in US tabloid The New York Post. A mysterious source who was potentially Britney Spears speaking in a British accent – who is to say? But it’s been gleefully repeated across the internet regardless, another apparently deserved blow to a man who has spent the past few years not as a singer or an actor, but as the internet’s favourite punching bag. His arrest, and the subsequent release of his pale, mortified mugshot, is just further ammunition. And proof that no one quite knows what to do with a pop superstar stuck in that difficult netherworld between young, blockbuster superstardom and nostalgic, late-in-life reappraisal. It begs a simple question: what are we to do with Justin Timberlake?

Timberlake has faced a wave of negative press over the past few years, often in relation to two women: Janet Jackson, who took the heat solo for flashing a nipple during their musical performance at the Super Bowl in 2004, and Timberlake’s ex-girlfriend Spears, whose time in the spotlight – and her treatment in the wake of their high-profile break-up – has been substantially reconsidered in recent years, both in numerous documentaries about the star as well as her own 2023 memoir.

That Timberlake was able to skate by on his white, male likeability while the women around him experienced substantial criticism and mockery – to the extent that Timberlake was once dubbed “the Teflon man” by People Magazine – has made him irresistible cannon fodder for online fans of Spears and Jackson who are eager for retribution, no matter how late it arrives. Even if neither Jackson nor Spears themselves appear to want it.

Often this criticism veers into ahistorical nonsense, discounting Timberlake’s magnetism at the height of his fame, and framing him largely as a lucky benefactor both of Spears’s uber-celebrity and the production work of Timbaland, his longest-standing musical collaborator. While both Spears and Timbaland served fundamental roles in the genesis of Timberlake, it’s lazy to discount his own appeal. In his prime, Timberlake was a brilliant pop star, a hip-shimmying, falsetto-voiced banger machine. The jittery carnality of “SexyBack”; the MJ-aping boppery of “Rock Your Body”; the slippery, sensual brattiness of “What Goes Around... Comes Around”. Yes, he had terrible hair. And said a bunch of frat-bro nonsense about Spears’s virginity. And that blaccent would frankly make Iggy Azalea blush. But it all worked! Timberlake was a product of his time and a very good one at that. Perhaps that should have been the extent of it.

Today, Timberlake occupies an odd space in popular culture. His most recent album, Everything I Thought It Was, was a commercial bomb, The Independent’s Helen Brown saying it was “about as sexy as a soiled mattress”, while reports have claimed that tickets aren’t exactly shifting for his world tour. March also saw Variety name him and Jennifer Lopez – another Nineties star to experience a year of relentless and often unnecessary mockery online alongside a flurry of unsuccessful new material – as figures struggling to “age gracefully” in the public eye. A high-profile arrest couldn’t have come at a worse time.

At the age of 43, Timberlake is a bit too young for nostalgia money to start rolling in. Half-hearted reunions with his star-making boy band *Nsync – such as their brief cameo in Timberlake’s animated Trolls franchise of movies – haven’t set the world alight, either, suggesting it’s also too early for a proper comeback tour. His lack of continued commercial success – 2018’s Man of the Woods, in which he reinvented himself as a folksy singer-songwriter in plaid and blue jeans, wasn’t a bomb by any means, but its singles had little traction on the charts – also suggests he hasn’t quite cultivated an audience of die-hard fans over the years.

Timberlake in his heyday in 2004, posing with two Grammy awards (Getty)

So where does that leave him? Timberlake shouldn’t necessarily disappear entirely, but it may be smart for him to drop off the map for a while, and to avoid trying to replicate a kind of stardom that no longer exists. Everything I Thought It Was had been preceded by limp promotional imitations of Timberlake’s past hits: a surprise appearance on Saturday Night Live in which he aped an old skit; ultimately nothingy hints at an *Nsync reunion; daily teasers of his new material, which tended to be recreations of the slinky pop-R&B of his heyday. None of it felt particularly new or interesting, and it was unclear what kind of listener Timberlake was playing to. Going away, cultivating a new and less regressive sound, and actually making people miss him might be the way forward. Or, if that doesn’t work, hang on for a decade or two until tweens of the Nineties decide they’re hungry for a new *Nsync show.

What all of this doesn’t mean, though, is that it’s fine to mock him at his lowest, either. Gloating over his arrest feels misplaced and mean, and invoked in the name of women who seem perfectly content letting bygones be bygones. Timberlake absolutely screwed up a bunch in his twenties, but insisting he pay for his not-exactly-ghastly misdeeds long into his forties is a waste of everyone’s energy. Let the man live. Just don’t let him get behind the wheel of a car any time soon.