From ‘President of Pop’ to embarrassing uncle: The sad decline of Justin Timberlake

Once invincible, now cringe: Justin Timberlake
Once invincible, now cringe: Justin Timberlake

In February of this year, Jimmy Fallon interviewed his old buddy, Justin Timberlake. For anyone who hasn’t kept up with the increasingly cloying tone of the US talk show circuit, it is an excruciating watch, consisting largely of Fallon babbling about how talented Timberlake is: “Then you dance! No one else dances. There’s no one like you. You’re one in a zillion buddy.”

The air is thick with Hollywood bro talk and backslap. Fallon reads out Timberlake’s tour dates, and gets the crowd to whoop after each one. It’s like we’re eavesdropping on the private conversations of two good friends, who have no idea what friendship is nor how to speak to anyone. “This album. I love it so much. Get ready for this. This thing is a masterpiece.”

As big PR pushes go, it felt like a push too far. A protesting-too-much that only adds to the sense of rear guard action presently surrounding the one-time “President of Pop”. Right now, Justin Timberlake seems to be watching a pop culture sinkhole open up before him – and he knows he has around three months to plug it.

Musically inert, increasingly presented as “the bad guy”, a quarter century into his career, the odds are against him as never before. Where once his timing was impeccable, the winds of history always at his back and he now finds himself becalmed in mid-life. He is having to make his own luck for a change – and it doesn’t much suit him.

Justin Timberlake's mugshot after being arrested on June 17
Justin Timberlake's mugshot after being arrested on June 17 - SLMIA

So now, just as once, when he was winning, he was always winning, today losses beget losses. This week, with his new album going nowhere slowly, Timberlake was photographed leaving a police station in the exclusive New York suburb of The Hamptons, in handcuffs, following a Driving While Intoxicated incident.

Rapidly, the many enemies he has garnered down the years sprang into action. The Free Britney Army, a loose but vast collective of fans of his ex, began to mass purchase her 2011 single, Criminal, in an attempt to push it into the charts. Many also chose the moment to dredge up an infamous 2007 quote, where he implored Spears to stop drinking.

It’s been a decade since Timberlake last tasted genuine pop cultural relevance, with The 20/ 20 Experience. Later the same year he released The 20/20 Experience Part 2. Effectively two double albums, of often eight minute long songs: a Prince-level masterclass in failure-of-editing. Despite these handicaps, the project’s brassy neo-soul solenoid managed to turn over the motor of global pop one more time.

In 2016, he had an unexpected hit with a one-off song he wrote for the Trolls kids film: Can’t Stop The Feeling. It wasn’t in keeping with his canon, yet was so effortlessly infectious that they let him open the Oscars with it. Then, in 2018, Timberlake retreated into his woodshed and came out holding a proper turkey. Man of the Woods.

This was a deceptively dull collision of country tributes to his Tennessee roots, and the breezy pop of his long-time co-writers The Neptunes at its most saccharine. Timberlake has never been renowned as a lyricist. Who could forget the likes of: “They call me candle guy, simply because I am on fire” from My Love (2006). Or “She killed me with that coochie-coochie-coo” from TKO.

But on Man of the Woods, without the clubland leading edge of his earlier works, all of that weakness was on display. “Then your hand’s talkin’, fingers walkin’, down your legs” went the title track. “Hey, there’s the faucet. Someone’s knockin’ like they know. But baby, don’t you stop it, yes, I’m watchin’/ Your hand slides down the light. And girl, you know.”

Forget turning off the faucet, it seemed it might be time to turn off the oxygen supply. Man of the Woods was a warning to all about the dangers of making an album simply because you look really good in a red flannel check shirt.

It did continue his unbroken run of platinum albums – but it took a full three years to limp its way to platinum status. That year, 2018, can now be seen as a point of inflection in the life of JT. That was the year he returned to the Superbowl – scene of The Wardrobe Malfunction – this time, as a solo headline half-time act, rather than Janet Jackson’s wing-man. But as if in a fable, returning here seemed to demagnetise his aura of invincibility.

That year, the Superbowl was being held in Minneapolis, so he’d decided to perform “with” hometown hero Prince, whose image was projected onto a giant white sheet next to Timberlake’s piano. Which was odd on two counts. Firstly because he and The Late Artist Formerly Known As had traded several barbs in the press down the years. Secondly, because Prince had explicitly spoken out against the practice of reviving dead artists like Tupac for post-mortal coil “concerts”. It seemed thoughtless at best, that a one-time rival would go against the stated intent of the deceased.

Later, he performed Rock Your Body. The song that had caused the wardrobe malfunction, yet didn’t see fit to mention Janet Jackson, and stopped the song at the line just before the malfunction had happened.

Timberlake (second from left) as part of NSYNC
Timberlake (second from left) as part of NSYNC - Ron Galella

“Timberlake’s magic didn’t take,” adjudged NPR. “It seemed like he’d cast the wrong spell, making himself invisible within swarms of dancers, programmed beats setting up choreography that just looked wrong for the weird Walking Dead ambience.” It didn’t help that his own woodsman outfit made him look like a more fashion-forward Ned from South Park

Now, more and more, the fluff of scandal began to stick to a velcro hide. In 2019, he was snapped holding hands with Alisha Wainwright, an actress, on Bourbon Street in New Orleans, half a decade into his marriage to another actress, Jessica Biel. For the man once commonly known as Trousersnake, fidelity has been an ongoing issue that has occasionally reared up to bite him. Apologising for “being drunk” seemed of a piece: a narrative was ginning up that Timberlake was selfish: still performing the same bad boyfriend behaviour that can be excused at 26, but looks less endearing at 39.

From that germ, an internet cult has grown up around hating the one-time golden boy, fuelled in part, by the partisans of the Free Britney movement, flooding the internet with videos pompously titled things like “How The Internet Fell Out Of Love With Justin Timberlake”.

At the time, the Spears/Timberlake golden couple was a great marketing device for both partners. As the years have rolled on, each has occasionally continued to use it to puff their latest product.

Timberlake’s most notorious version of this was to make the Cry Me A River video – in which a blonde woman resembling his ex cheats on him, while he videotapes the encounter. In its day, it was perfect tabloid fodder – actively baiting the entertainment media to engage in endless Kremlinology. But times change. History’s crook is long. Just as a Zoomer generation recently raked over old episodes of Friends on Netflix, looking for problematics, so too here the revanchist read has become: “creepy”, “giving stalker vibes”, “slut shaming”.

In this new age, Timberlake has proved himself a flat-footed political communicator. In 2021, after the documentary Framing Britney Spears ignited the FreeBritneys, he issued the requisite mealy-mouthed formula that the times called for:

“I’ve seen the messages, tags, comments, and concerns and I want to respond,” he wrote. “I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn, or did not speak up for what was right. I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism.

“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.” Thereby both swallowing the implied premise of the complaints, and instantly sailing past their conclusion.

Noughties 'it' couple: Justin and Britney
Noughties 'it' couple: Justin and Britney - Getty

An apology should have been the end of that. But it never is. Last year, Spears released The Woman in Me, a memoir, in which she wrote for the first time about aborting Timberlake’s baby. In light of which the video for her song Every Time (Britney in a bright white virginal dress submerges into a bath; has some kind of blood-soaked medical emergency; wakes up in hospital) can be read as a very straightforward analogy.

Timberlake, Spears told the world, had pleaded with her to abort the baby. They weren’t ready, he’d apparently said: they had their whole careers ahead of them. As Britney’s enfeebled mental state became ever more apparent, the victimology swung ever more firmly behind her. Trousersnake The Cad is in internet jail for the foreseeable.

His sure-footedness no longer even extends to his feet. In 2022, at a concert in Washington DC, he decided to pay homage to the local dance phenomenon ‘Beat Ya Feet’. But the results were a tippity-tappity round of box-stepping dad dance that mystified his audience, and amused the wider world when the footage went viral. He ended up having to apologise for that too, acknowledging on Instagram that he had “two problems” before swinging the camera down to his shoes.

He even ended up apologising to black culture itself, after getting into a Twitter tangle, in 2016, with comments directed at actor Jesse Williams, who had just given a rabble-rousing pro-black speech at the Black Entertainment Television Awards. Once again, he ended up starting a fight he couldn’t finish with social forces bigger than his celebrity – rowing in behind basic liberal ideas of “we should treat everyone the same regardless of race”, then rowing back out rapidly when it became obvious that this was no longer the timbre of the times. The usual apology with the usual craven blandishments was furnished.

Perhaps he got sick of apologising, however, because in February this year he went viral, again, for telling a concert audience “I would like to take this opportunity to apologise to absolutely f---ing nobody.”

His acting career, which began in a blaze with The Social Network, continued in fine style with his turn as a gormless folkie in 2013’s Coen brothers flick Inside Llewyn Davis, seems to have fizzled out into an ongoing voiceover role in the Trolls franchise.

All of which means that, as he sought to re-launch himself on the world, his Furby-eyed Tennessee charm had to stretch a long way. Selfish, the unfortunately-named lead single of his new album, Everything I Thought It Was, gave us the classically ungainly Timberlake couplet: “It’s bad for my mental/ but I can’t fight it when you’re out looking like you do.”

Elsewhere, album opener Memphis chimed in with the mortal lines: “I lost my voice like a pastor/ faster than a Harlem shimmy. But I guess that’s the price you pay/ for trying to make heartbreak pretty. They say life’s a bitch/ So please, if you’re penning my eulogy/ just say I tried.”

Eighteen years ago, the jarring futurism of second album lead single SexyBack announced the comeback of a pop king ready to drive his enemies before him and hear the lamentations of their women. But Selfish evoked a spirit of slight return. Did you miss me? It said. I can still do some of the things you remember me for. If you’d like that.

The reviewers saw the whole thing that way, and missed no opportunity to put the boot in. “A slog enlivened by some surprising moments,” concluded NME. “[Exhibits] a misplaced confidence that can only be described as Timberlakean,” Pitchfork suggested. “Laboring for such a long, long runtime under the misapprehension that a risk-averse mop bucket of last decade’s trending sounds is gonna hit.” “An album that’s everything you thought it was but has nothing to say,” said SPIN.

It presently languishes at 51 per cent on reviews aggregator Metacritic. He missed the Billboard number one, and recorded the lowest first week sales of his career. Somehow, it seems as though Jimmy Fallon may have been insincere.

Of course, some of this wave of sag was always inevitable. No one can be top of the heap forever. But the degree to which decline can be managed and dignity retained obviously matters to every midlife pop star. Whatever Britney does, however bizarrely she tumbles on, she will always have a certain aura. On the other hand, Timberlake is fundamentally too normal for that. He will always have to sing for his supper.

As youth ebbs away, people do change and so do priorities. For most, living well becomes more important than cresting the heap. He has two small boys and a wonderful wife, Timberlake told Graham Norton earlier this year. He was just… happy. Is that a crime these days?

Fair point. But as a lyrical theme, domestic bliss has only ever undergirded albums of the quality of Double Fantasy. And, after he was observed by Hamptons police driving through a stop sign and swerving into a lane of oncoming traffic at 12:37 AM on an idle Tuesday morning, well, it must be asked: is he even that?