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Where Can Justin Timberlake Even Go From Here?

Has a comeback ever been more poorly timed? Approval ratings for Justin Timberlake have dipped lower each year, coming to a head when Britney Spears’ memoir The Woman in Me was released a few months ago and unveiled intimate drama from her relationship with the “Cry Me a River” singer. 

It’s not like his reputation had been particularly stellar over the last several years. A reckoning with the way the media treated Spears in relation to her once-beloved ex overlapped with a reckoning for Janet Jackson, who had to publicly grovel after the Super Bowl wardrobe malfunction. Timberlake, meanwhile, exited the situation unscathed. 

As Timberlake has been rolling out his new single “Selfish,” the response has ranged from tepid to fury. It’s not Timberlake’s best work but also not horrible; it sounds like a watered down version of Nick Jonas’ “Jealous,” which was a song that had Jonas cosplaying as Timberlake in more ways than one can count. And in Timberlake’s own love song canon, its subtleness feels off-brand, given that this is the same man who wrote the luxuriant “Mirrors.” Chart-wise, it was a disaster: The song debuted lower than Ben Shapiro’s “Facts.”

There was a time in the not-so-distant past that people begged for a new Justin Timberlake album, almost as passionately as everyone has been begging for Rihanna’s. His post-*NSYNC solo career was a blockbuster, with the teen idol-shedding Justified teeing up a R&B-pop homerun with FutureSex/LoveSounds. For that era, both albums were the rare perfect storm in pop music of being both critically acclaimed widely beloved. And for a member of a disbanded boy band looking for career longevity, that was no simple feat. 

After FutureSex spawned three Number One hits, nine Grammy nominations (over two ceremonies, nonetheless) and a massive tour, Timberlake took several years off from releasing new music, instead focusing on acting to varying degrees of success. His biggest win in Hollywood was a turn as Napster founder Sean Parker in The Social Network, but he otherwise became a leading man in a string of popular but middling comedies that showed off his comedy chops less effectively than his appearances on Saturday Night Live with Andy Samberg and Jimmy Fallon. 

Shockingly, after seven years without new solo music, Timberlake’s sprawling, two-part The 20/20 Experience from 2013 lived up to all the hype and anticipation and included a co-headlining stadium tour with Jay-Z. 

Two decades of being pop’s golden boy has made Timberlake’s fall out of public favor feel so much heavier. His roots-y turn on Man of the Woods was a Number One album with the most mixed reviews of his career. But then, his third appearance at the Super Bowl Halftime Show, this time as a solo headliner, was the first inkling of a true shift in opinion. His 2004 appearance at halftime, where a last minute-added dance move with Jackson ended in a major wardrobe malfunction, was a specter over his return. Conversations had just begun about how wronged Jackson had been in the fallout, where the blame entirely fell on her as she was forced to publicly apologize and bear the brunt of the blame, shame and embarrassment. Timberlake’s career continued to flourish while Jackson’s floundered in the immediate years following. The day of Timberlake’s Super Bowl return in 2018 became the first, unofficial Janet Jackson Appreciation Day, where fans celebrate her career on social media.

Similar reckonings were happening with the treatment of Timberlake’s ex Spears over the next few years. The two dated in the early 2000s, as both were at the first peak of their careers as teen idol superstars. Given their squeaky-clean images, their break-up and some unsavory accusations from both parties created a media frenzy; Timberlake accused girl-next-door Spears of cheating on him and even referenced this in the not-so-subtle video for “Cry Me a River.”  The song was a hit and Spears’ reputation was effectively tarnished. Spears’ career, however, still thrived and her decision to lean more into the vixen image she was forced into was a smart move. However, the effect of tabloids contorting her into a dangerous woman meant that she endured a type of scrutiny Timberlake often avoided from the media. His Hollywood life and relationships, while well-documented, were flashier in comparison to the type of hunting-season coverage of Spears’. 

Spears’ recent book was full of Timberlake revelations, painting a portrait of teenage puppy love that ended in insurmountable heartbreak for Spears. She opened up about a secret pregnancy and how the pair decided to terminate it. She also let readers in on her side of their break-up, since Timberlake had been the one to most publicize his anger. He had painted her as the philanderer, while Spears notes he had been sleeping around while on tour. She was devastated that their relationship had come to an end — via text message, of all things — and even more devastated that she was now painted as the evil woman who broke his heart.

Online, the mere mention of Timberlake has become a launching point for disgusted and angry replies. It has even led to revisionist history, with many pretty egregiously claiming that his career has always been middling and even dead in the water for much longer than is actually true. Defenses from both Spears and Jackson have barely helped. Jackson’s recent documentary cleared up the events that led up to the wardrobe malfunction, which was ultimately due to last-minute choreography changes that Timberlake learned shortly before they stepped on-stage. Spears posted on Instagram apologizing for what she wrote in her book (though days later, after Timberlake said he “apologizes…to absolutely nobody,” she made a new post about “someone talking shit” about her and threatened legal action). 

Not even teasing a *NSYNC reunion has helped Timberlake. He reunited the band for a song on the Trolls Band Together soundtrack that didn’t make much of a splash. And while promoting “Selfish,” he alleged they recorded more music together.

Weirdly, Timberlake pulling himself up out of this career hole seems more difficult than it would be for artists who have done much more damning actions. Timberlake’s worst crimes have been that he is a privileged white guy and a pretty shitty boyfriend. Of course, it doesn’t help that both his new single and most recent album were not the best showcases of his abilities. And also doesn’t help that the shitty boyfriend allegations come from one of pop’s most beloved figures who has endured some of the most horrific music industry treatment in star in history has endured.

His attempt to move on may have come much too soon; he is no longer the type of untouchable pop star who can simply ignore bad press. His continued insistence as positioning himself as a Family Man first and foremost is a weak defense, toppling at any reminder of the women who helped brighten his star and were left to pick up the pieces when he moved on. And his reliance on the old tricks that made him likable in the past (using the boy band he quit to muster up good press; reviving old, viral Saturday Night Live characters during an episode he wasn’t even hosting) are just not enough. 


Oddly, his comment on not apologizing was the most interesting part of this rollout. Leaning into his new role as pop’s main villain at the moment is more seductive than trying to make his image as wholesome as possible. 

Or at the very least this will be enough to bully him into an actual *NSYNC reunion tour. Maybe nostalgia can work for instead of against him for once. 

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