Hey, do you want to hear the whitest sentence in the English language? It’s “Justin Randall Timberlake was arrested on a DWI charge in Sag Harbor on a Tuesday.” God, just typing those words is enough to summon the phantom taste of potato salad with raisins in it.
Poor Justin Timberlake. He’s had a tough few years, hasn’t he? He’s likely not used to all the bad press after decades living in the light as favored *NSYNC son. But indeed, on June 18, he was arrested in the Hamptons on suspicion of drinking and driving. His mug shot—bleary baby-blue eyes—has already been republished a thousand times. His reported words upon being arrested—a pitch-perfect setup and punch line, if Page Six is to be believed—have also already been transformed into an endless roll of memes. No argument there: This may indeed ruin the world tour.
Gen Xers and millennials are hard-pressed to remember a time when Timberlake wasn’t a dominating cultural force. When *NSYNC’s first album charted in 1998, he was the clean-cut, well-liked boy-band idol who had ramen for hair. When he went solo in 2002, with Justified, the public was too distracted by how good “Cry Me a River” was to appropriately recognize how stupid an album name—and his accompanying fedora—that was. Since then, Timberlake has remained one of our most enduring celebrities. He charmed with his tearful anxiety on Punk’d (someone put Ashton Kutcher directly under a jail) and delighted with his Barry–and–Robin Gibb routine with Jimmy Fallon on Saturday Night Live. He dated Britney Spears, then publicly accused her of cuckolding him; he might as well have branded her with a big ol’ SLUT straight across her forehead. In 2004 he performed at the Super Bowl halftime show with Janet Jackson; in an incident that taught the world the words wardrobe malfunction, Timberlake ripped off Jackson’s top and exposed her breast, hurling her into a vortex of public shaming. In the aftermath, he won two Grammys.
For a good decade and a half, it seemed as if Timberlake was untouchable. He was at the outskirts of a thousand scandals but never faced any serious repercussions himself. He was impish, was arrogant, and had been famous since childhood—there didn’t even seem to be consequences from his wife, Jessica Biel, after he was photographed in 2019 holding hands with his Palmer co-host Alisha Wainwright. “I should have known better,” Timberlake wrote in a Notes app apology, which I can only assume was viewed by millions more people than ever saw Palmer.
Timberlake, whether or not he realized it, had been walking on fractured ice for the past few years. The tide first started turning on him after Spears’ conservatorship was covered in Framing Britney Spears, and her own public reckoning took the form of celebrities, comedians, and regular folk on the internet apologizing to her endlessly for how we mocked her in the early aughts. Shouldn’t her ex-boyfriend, guilty of helping kick off the trend in the first place, also say sorry? Her memoir, as well as the several documentaries chronicling her media treatment, painted Timberlake as, at best, a hapless Caucasian goon yelling “fo’ shiz, fo’ shiz” at Ginuwine. At worst, in hindsight, he was cruel and selfish, allegedly cheating on Spears privately while dragging her through the mud publicly, burying her in the unique kind of bad press that only a woman can suffer from. Jackson’s scandal also got the documentary treatment, similarly reminding the world that Timberlake was half of the equation of the lowest point in her career and yet had borne none of the consequences when he ripped off her top. His apology to Jackson was 17 years too late.
It’s not necessarily surprising that a very rich, very famous man was arrested on suspicion of having a few too many and driving around Sag Harbor, a town beloved by wealthy elites looking to escape Manhattan for the summer. What’s striking here instead is the schadenfreude being squeezed out of this story. No detail is too small for the gossiping hordes to consider: the baby-faced arresting cop who allegedly didn’t even know who Timberlake was (mortifying), the bartender who confirmed that the singer had indeed ordered just one drink, the New York Times reporter who was dispatched to Sag Harbor to cover this vital story, only to get dogged by locals.
But the online glee around Timberlake’s downfall could never have happened overnight. For years, quietly then increasingly vocally, a swath of frustrated pop culture fans have resented Timberlake. They grew up with him, like he said recently at the Chicago stop of his aforementioned world tour, as he thanked the crowd for “riding with” him after his arrest. Those spectators have sat front row to the reality that he’s no longer a cutie-pie 24-year-old whose album we never take out of our CD player—he’s the 43-year-old guy from your hometown who won’t stop talking about that one big play he had as captain of the football team. As the mainstream culture’s collective understanding of gender and racial politics has shifted, we see Timberlake’s role with more clarity. He’s not the idol anymore. He’s out of step with the zeitgeist; the public can better view his murky history with women, from Britney to Janet to, of course, his long-suffering wife, who did nothing wrong except for stealing from her siblings’ piggy bank on 7th Heaven.
A loud, comical backlash has been brewing for years, waiting for one more misstep to break the dam on these decades’ worth of pent-up feelings about Timberlake. Drinking while driving is a perfect one for a now-resentful audience to latch on to; it’s an easily preventable crime that suggests entitlement and a lack of consideration for other people’s well-being. Timberlake’s downfall, as suggested by the breathlessness of tabloid coverage and online reactions, is tinged with delight; if he can tumble this low, that means just about any previously invincible man can. And, hey, maybe they should.
It’s difficult and even a little painful to guess at what runs through Timberlake’s mind when he has moments to himself, in the wake of this string of nadirs after a career that went up and up and up. Does it bother him that his Madison Square Garden concert—which takes place tonight—hasn’t sold out? What about the even-emptier Wednesday show? Is he haunted that his most recent album, supposedly a big comeback after years of inactivity, outright flopped? Does he yearn for the days when he could present himself as a cup of soup on SNL, or in some brain-dead sketch with Jimmy Fallon (who has similarly been battling bad press after years of being the good guy), and the audience would fall over themselves with joy? It must be hard now, living in the quiet and the contempt that remains.
But that’s the thing about figures like Timberlake, isn’t it? We get older; they stay the same age.
