Where it all went wrong for Justin Timberlake: Teenage brat behaviour, thousands of unsold tour seats and THAT red-eyed mugshot - ALISON BOSHOFF retraces the slow decline of a teen heartthrob

Whatever state he was in on Tuesday night – and police say he was glassy-eyed, smelled of booze and had allegedly run a stop sign – the moment that he was stopped for suspected drink driving was also a moment of clarity for Justin Timberlake.

‘This is going to ruin the tour,’ the 43-year-old popstar apparently muttered. The New York officer – woundingly too young to recognise Timberlake - asked, ‘What tour?’ only to be told: ‘The world tour.’

Timberlake, as we shall see, has always had a hawk eye for the bottom line and he will be painfully aware that ticket sales for The Forget Tomorrow World Tour weren’t great even before this latest, embarrassing mis-step.

Yesterday, hundreds of seats remained unsold for his next show, in Chicago tomorrow night, including 60 in the three sections closest to the stage. Further away from the front, up to 70 were still available in a single section.

It’s the same story at Madison Square Garden in New York, which is his next stop on Tuesday night. Eighty seats in the sections closest to the stage are also unsold there, with more than 100 unfilled in single sections further back.

Justin Timberlake apologized to his 'shocked' tour crew on call just hours after his DWI arrest

The pop star has two upcoming shows in Chicago later this week followed by back-to-back nights at Madison Square Garden in New York City next week; seen in April

A map of both stadiums, showing the sold out sections in grey and those still with availability in blue, is enough to drive any artist to drink (Pictured: Availability for the show in New York)

A map of both stadiums, showing the sold out sections in grey and those still with availability in blue, is enough to drive any artist to drink.

Indeed, his red-eyed mugshot – already going viral along with gags about him apparently telling cops he’d only had ‘one Martini’ – serves all too well as a portrait of a past-it Prince of Pop.

As the New York Times observed in their skewering review of his latest album earlier this year: ‘Timberlake is hardly the most despicable person in show business and his greatest offence was...blithely benefiting from white male privilege and throwing his less charmed counterparts [including Britney Spears, of which more later] under the bus.

‘If he were still making music with the conviction and the artistry of FutureSex/LoveSounds [Timberlake’s 2006 hit]... maybe he could be forgiven.

‘But the truth is, just as that Teflon coating is beginning to erode under the glare of cultural scrutiny, Timberlake’s music has begun to lack zest.’

That album, Everything I Thought It Was, did not go to number one and, unlike the smash hits which have brought him ten Grammy awards and over 100 million albums sales, has failed to re-establish his relevance. Gen Z know him as the voice of the Trolls films; Millennials have outgrown him.

Meanwhile, the fallout from one time lover Britney Spears’ memoir, The Woman In Me, caused him to be cancelled by a new generation who have never even engaged with him as an artist.

He did not emerge with credit from her published account of their romance – and, even worse, he refused to apologise for hurting her by allegedly demanding she abort their child, and by casting her as a cheat in his music video for Cry Me A River.

Not long after publication, at a free concert in Manhattan in February this year, he introduced the song with the words: ‘I’d like to take this opportunity to apologise... To absolutely f****** nobody.’

It’s the behaviour of a teenage brat, all the more dismaying from a man past 40, who is married with two children who he says he tries to inspire.

So where has it all gone wrong for Justin?

Justin Timberlake was arrested for driving while intoxicated after having drinks at Sag Harbor's American Hotel in New York on Monday night (pictured) 

Justin, 43, turned to alcohol after being caught up in controversy last year following allegations made by Britney Spears, insiders previously told DailyMail.com 

Flip-flopping between music and film has arguably not served him well. 

He took a complete break from the music business for six years from 2008 and made some movie hits like The Social Network and Friends with Benefits, but there were some rather less well-received appearances in the Yogi Bear movie and Shrek The Third. 

At the time he said: ‘I can give you my personal opinion: love the music, hate the business. It’s a screwball business and there are a lot of players who will straight-up lie to you.’ He seemed confident that the fans would be there when he returned.

‘Thus far when I’ve followed my gut instinct I’ve been right, and when I’ve gone against it I’ve made the wrong decision, so it’s cool,’ he said in 2010.

While there have been hit albums and tours since then, notably the 20/20 Experience in 2013, his latest album has disappointed and there is a sense of a law of diminishing returns setting in, rather than the building of a solid musical legacy.

Financially, he need have no worries. Guided by IMG during his golden years he was one of the first celebrities to have his own range of booze and clothes, and to endorse perfume. He accepted $6million (£4.7million) in 2003 to sing the McDonald’s jingle, I’m Lovin’ It – and turned down a $2.5million (£2million) offer from Bud Light to do the same for them because it just wasn’t enough dough.

‘I don’t feel guilty about success,’ he said. ‘You can’t feel guilty about aspiring to be good at something.’

Raised in Memphis, Tennessee, Timberlake always wanted to be famous and took part in the TV show Star Search, singing country music aged 11. Soon afterwards he became one of the Mouseketeers – alongside Britney, Christina Aguilera and Ryan Gosling – on the All New Mickey Mouse Club.

As a teenager he achieved fame with NSYNC, who remain the fifth highest selling boyband of all time.

Perhaps there’s a bit of arrested development in play thanks to the fact that he didn’t have a normal childhood; he lives like a teenager who has won the lottery. He collects Nike trainers, and has more than 400 pairs. Earlier this year he spent $22,000 on a single trainer collecting spree, snapping up a rare pair of Red Octobers from 2014.

Raised in Memphis, Tennessee, Timberlake always wanted to be famous seen in September 2009

As a teenager he achieved fame with NSYNC, who remain the fifth highest selling boyband of all time

When he was in his late 20s he converted one of the reception rooms in his house into a putting lawn, and had a five-hole golf course put in the garden. He then added a 1,000sqft tree house as a den for him and his friends to play cards and drink in. Reports suggest Timberlake, then 29, hung a distinctly juvenile ‘No Girls Allowed’ sign on the door.

By then he was dating Hollywood actress Jessica Biel, whom he married in 2012.

Before Biel, 42, he had a reputation as a ladykiller and was sometimes referred to as ‘Justin Trousersnake’. 

He’s said to have cheated on wife Jessica with X-Men actress Olivia Munn, which he denied; on ex-girlfriend Cameron Diaz with Scarlett Johansson (who played his love interest in the music video for his hit single What Goes Around... Comes Around in 2007); and on Britney with unnamed - but reportedly numerous - women. 

As he candidly said in 2006: ‘I’m just like everyone else, I get completely plastered, I’ve done my fair share of drugs and I’ve been caught places with my pants down.’

Getting together with Britney, his first girlfriend, in 1999, propelled them both to pop superstardom. The pair began dating when they were both 18. The relationship ended in March 2002 amid rumours she had been unfaithful to him with choreographer Wade Robson. Timberlake’s hit Cry Me A River was supposed to have been about her betrayal.

Britney later said she felt as if she’d been portrayed as ‘a harlot who’d broken the heart of America’s golden boy’.

Her recent memoir told a different story. While she admitted to cheating on Timberlake ‘one time’ by kissing a backing dancer, she added that ‘there were a couple of times during our relationship when I knew Justin had cheated on me’. 

She also revealed that she had gone through with an abortion at his urging, writing: ‘Justin definitely wasn’t happy about the pregnancy. He said we weren’t ready to have a baby in our lives, that we were way too young... I agreed not to have the baby. I don’t know if that was the right decision.’

Britney Spears is toasting to 'the little things' in life' in wake of her ex-boyfriend Justin Timberlake's shock DWI arrest

Spears dated Timberlake from 1999 to 2002; pictured 2002

His performance with Kylie Minogue at the 2003 Brits was so raunchy that stories circulated that he spent that night in a hotel room with the Aussie singer – although other reports suggested that actually he bedded Kylie’s sister Dannii that night. Dannii has since said that she didn’t succumb to his advances – Kylie, though, was observed having a blazing row with then-boyfriend James Gooding.

Timberlake’s womanising image has been softened by his 12-year marriage to Biel, whom he refers to as ‘the boss lady’ and said in an interview: ‘Every once in a while, I can catch a glimpse of her when she doesn’t see me looking. I have this moment where I’m like, “If you only make bad decisions for the rest of your life, you made one really good ­decision.”’

However, it’s not been plain sailing. In 2019, Timberlake publicly apologised to Biel after he was pictured holding hands with his co-star Alisha Wainwright during the filming of drama Palmer in New Orleans, saying: ‘I drank way too much that night and I regret my behaviour. I should have known better.’

In 2022 he and Biel renewed their vows as part of their 10th wedding anniversary celebrations, with Justin gushing on Instagram: ’10 years ain’t enough! You make me a better husband and father every day! I love you so much you beautiful human!’

Time will tell if his ‘beautiful human’, currently filming Amazon Prime show The Better Sister in New York, still feels quite the same way about him.