Opinion | Oops, Justin Timberlake Did It Again

Poor Justin Timberlake … are not three words I could have imagined typing 25, or 15 or even five years ago.

Mr. Timberlake, the “Mickey Mouse Club” veteran turned boy band pinup; half — along with Britney Spears — of an iconic millennial power couple; the platinum-selling Grammy-award-winning solo artist and a go-to “Saturday Night Live” guest host; and now, as the whole wide world has learned, the dude arrested in the Hamptons early Tuesday morning and charged with driving while intoxicated.

Sprinkling salt on the wound, Page Six reported that the arresting officer didn’t know who the perp was. After Mr. Timberlake reportedly muttered that the arrest was “going to ruin the tour,” the officer asked, “What tour?” Per People magazine, “the internet can’t stop laughing.” Among the cascade of jokes: that his arrest might be the one event that could turn all of X pro-cop for a day, or that Mr. Timberlake should have been more concerned with taking a cab back than bringing sexy back. Streams of Britney Spears’ song “Criminal” spiked. Savage memes keep replicating.

The misery of celebrities always occasions a fire hose of schadenfreude, but this seems next level. Where, I found myself wondering as I scrolled and LOL’ed, are the fans rallying to his defense? Why is everyone enjoying this quite so very, very much?

The answer is that this isn’t happening to any old celebrity. It’s happening to the man who for the longest time seemed, to many, like the embodiment of unearned good fortune — in a word, privilege. He’s a talented performer, a gifted singer, a charming actor, sure. But his biggest talent may be for getting away clean.

Over the years Mr. Timberlake has not been immune to controversy, just to its consequences. Time after time, he escaped unscathed, looking and, it seemed, feeling just fine, while those around him were left to pick up the pieces.

When Mr. Timberlake and Ms. Spears broke up in 2002, his story — hinted at in interviews, acted out in music videos and implied in mash-ups of “What Goes Around … Comes Around,” “Rehab” and “Crazy” — was that she’d cheated and broken his heart. The world was happy to take his word for it. “You did something that caused him so much pain,” Diane Sawyer said to Ms. Spears in an interview in 2003. “So much suffering. What did you do?”

Then, in 2004, Mr. Timberlake joined Janet Jackson during her Super Bowl halftime show. You know what happened next: At one point the choreography called for him to pull off a panel of her bustier, but because of what would later, and still remarkably, be euphemized as a wardrobe malfunction, almost her entire breast was exposed. For some reason, Ms. Jackson was publicly excoriated. A week later Mr. Timberlake won a Grammy for best male pop vocal performance, at a show from which Ms. Jackson had been disinvited.

Along the way, some observers started calling Mr. Timberlake out for what they saw as appropriating from Black culture (R&B, gospel and hip-hop), but not standing up for Black people. It didn’t stop single after single from topping the charts.

In time, the Black Lives Matter movement helped make more people willing to think about the role that race plays in determining who succeeds and who fails, whose career stalls and whose soars, who walks away from a traffic stop. And the #MeToo movement left people more skeptical of male misbehavior and more willing to believe women. When Ms. Spears’ memoir was released last year, she told her side of the story: that Mr. Timberlake was the one who’d cheated, and then dumped her via text message. She also revealed that she’d become pregnant, and that he had insisted on an abortion, during which he played the guitar while she writhed in agony on the bathroom floor.

This time around, many readers seemed willing to believe her. They also seemed delighted by the chance to mock him — even Michelle Williams, who narrated the audiobook, had way too much fun mimicking him as he supposedly said, “Oh, yeah! Fo’ shiz fo’ shiz! Ginuwine! What’s up, homie?”

In 2021, after the release of a documentary about Ms. Spears, Mr. Timberlake took to social media to make amends.

“I specifically want to apologize to Britney Spears and Janet Jackson both individually because I care for and respect these women and I know I failed,” he said. “I also feel compelled to respond, in part, because everyone involved deserves better and most importantly, because this is a larger conversation that I wholeheartedly want to be a part of and grow from.”

That Justin Timberlake — the one who has emerged over the last few years — looked less like a pop Prince Charming, more a serial exploiter of women and of Black music and culture, a man who has enjoyed unearned privilege and undeserved successes, who has been served that long-awaited slice of humble pie. Which is why plenty of people were so eager to view his arrest this week as a kind of deferred-karma comeuppance.

I was, I confess, one of those people. Some part of me wants to believe that if the ultimate Teflon-coated rich white dude is no longer so able to charm his way out of trouble, a larger cultural sea change might be underway.

But it’s the same part of me that wanted to believe that Donald Trump would be held to account for the “Access Hollywood” tape. Except he wasn’t.

It’s the same part that thought Christine Blasey Ford’s allegations would put a stop to Brett Kavanaugh’s chance to sit on the Supreme Court. Except they didn’t.

The same part that hoped that the allegations about which Matt Lauer said he felt “embarrassed and ashamed” meant he’d never so much as breathe the word comeback. Except he has. Repeatedly.

Canceled white guys rarely stay canceled. It seems like the best we can hope for is a chance to briefly hold them responsible for their actions. Meanwhile, the cultural tides that prompted people to reconsider Mr. Timberlake’s actions are shifting back — if they ever really shifted at all.

The corporations that adopted D.E.I. initiatives with such fanfare a few short years ago are retrenching, consolidating, or doing away with their diversity departments altogether. Republican lawmakers are eagerly banning D.E.I. in higher education. In publishing, many of the Black editors hired with such fanfare in the last few years have lost their jobs, while Black authors continue to account for less than 10 percent of novels published by major conglomerates each year. Meanwhile, Roe v. Wade is two years in the rearview mirror and Donald Trump, whose Supreme Court picks ensured its demise, is leading in the polls.

Remember that social media apology that Mr. Timberlake offered a few years ago? This past January, at a New York City concert, he announced that he apologized to “absolutely” — and here he interjected an expletive — “nobody.”

The memes are hilarious, the tweets are even funnier, but the likeliest case is that Justin Timberlake will be just fine. And even if he’s not, there will be other men like him lining up to take his place. The systems that let him flourish are even less vulnerable than the men who have long reaped their benefits.