Justin Timberlake’s DWI arrest is the latest in a string of controversies that have the marked the singer’s once illustrious career. 

The singer, 43, was arrested after he ran a stop sign while behind the wheel of his BMW X7 in the early hours of Tuesday morning after a night out with friends in Sag Harbor. 

Insiders say it is a much needed ‘wake-up’ call for Justin, who is in the midst of his The Forget Tomorrow World Tour. 

It is not the first run-in the singer has had with alcohol. In 2019, the Cry Me A River hitmaker blamed drink for putting on a cosy display with his co-star Alisha Wainwright. 

Now sources have told MailOnline, the singer has increasingly turned to drinking in the wake of Britney’s bombshell memoir, which was released last year, where she claimed she had an abortion because he ‘wasn’t ready to be a dad’. 

In the wake of Justin’s arrest, we take a look at the biggest scandals which have plagued his 30-year career in the spotlight…  

DWI arrest 

Justin was arrested after he ran a stop sign while behind the wheel of his BMW X7 in the early hours of Tuesday morning after a night out with friends in Sag Harbor. 

 Police described him as having ‘bloodshot and glassy’ eyes, smelling strongly of alcohol, having slowed speech and unable to maintain his attention.

The father-of-two performed a field sobriety test and was asked to take a breathalyzer test, which he refused.

A bleary-eyed Justin was seen emerging from the Hamptons police station in handcuffs. 

After a brief arraignment where he was banned from driving for a year in the state of New York, he was released without bail. 

For refusing the breathalyzer test, Justin had his driving privileges in the state of New York suspended. 

The singer looked shellshocked as he emerged from court wearing a baseball cap. 

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.

‘Arrest is a wake-up call after turning to drink following Britney Spears‘ bombshell memoir and pressure to stay in the charts’, say friends 

Insiders claim the incident should serve as a ‘wake-up call’ for the singer who used alcohol to cope with the explosive allegations leveled against him by Britney, 42, including he urged her to have an abortion in the early 2000s. 

On top of this, sources allege that he has been crumbling under the increasing pressure to compete with popular artists like Harry Styles – and has struggled with the lackluster performance of his latest album, Everything I Thought It Was, which failed to top the charts on its release in March. 

‘Justin has been stressed over the Britney drama that happened at the end of last year and some of us noticed that he was drinking more,’ a source told DailyMail.com exclusively.

‘He isn’t an alcoholic by any stretch, but he was advised to reel the drinking in so he could have a clear head when dealing with any public controversy because he had been accused of handling the Britney and Janet Jackson backlash poorly.’

The source continued: ‘The guys who were there last night didn’t want him to drive because they had been drinking, but they were ignored.

‘He is being cooperative now and is working with his lawyer Edward [Burke, Jr.] to help him work his way through it. His friends have wanted him to drop the booze for some time, so this is somewhat of a wake-up call.

‘The pressure of having to compete with artists like Harry Styles and Drake is getting to him and his numbers [album sales] being lower is definitely bothering him. 

‘We’ve all felt this for a while, and it has affected his writing process on his last few records.’

A second insider echoed the concerns, claiming Justin’s latest alcohol-fueled incident stems from a need to ‘escape’ following poor album sales.

‘It’s hard to say why anyone drinks but if it has to do with where he is at in his life right now, it makes sense to say he needs an escape,’ they said.

‘This will likely be his last successful tour and he is aware of this. He has a wife and two young kids at home.

‘He has not been super happy about his album sales but no one at the label really has. Everyone was expecting so much better.’  

A third source claimed his drinking habits are well known among those closest to him. 

‘It is no secret that Justin drinks, and the dancers know this better than anyone,’ they said. ‘He has turned up to rehearse smelling like alcohol on several occasions.’

The pop star has two upcoming shows in Chicago later this week as part of his Forget Tomorrow world tour, followed by back-to-back nights at Madison Square Garden in New York City next week.

The source said he often ‘celebrates a good show by getting drunk’ but can also become ‘flirty’ – with his wife Jessica joining nights out to ‘babysit’ him.

‘When he drinks, he gets super flirty, and Jessica does have to babysit him,’ they continued. ‘She has gone out with the crew several times.

Groveling apology after a ‘lapse of judgement’ on THAT cosy night out with co-star 

Back in 2019, Justin issued a grovelling apology to his wife Jessica Biel after he was caught holding hands with actress Alisha Wainwright on a night out. 

The singer blamed alcohol for his ‘lapse in judgement’ while on the night out in New Orleans, but insisted ‘nothing happened’ with his Palmer co-star. 

Justin addressed pictures which showed him placing his arm around Alisha before she tenderly rested her hand on his right knee. 

His statement on Instagram read: ‘A few weeks ago, I displayed a strong lapse in judgement – but let me be clear – nothing happened between me and my costar,’ he insisted in a statement on Instagram.

‘I drank way too much that night and I regret my behavior. I should have known better.

 ‘This is not the example I want to set for my son. I apologize to my amazing wife and family for putting them through such an embarrassing situation, and I am focused on being the best husband and father I can be. This was not it.’

The couple, who married in 2012, managed to put the drama aside and went on to welcome their second son Phineas a year later. 

Britney Spears accuses Justin of cheating and says she had an abortion because ‘he didn’t want to be a father’ during their three-year relationship in bombshell memoir

While Justin was at the height of his fame, he started dating Britney Spears – and immediately they became Hollywood’s ‘it’ couple, but they split in 2002.

The Hit Me Baby One More Time songstress recently reflected on the relationship in her memoir, The Woman in Me, and she accused Justin of being unfaithful to her.

‘There were a couple of times during our relationship when I knew Justin had cheated on me,’ she wrote.

‘Especially because I was so infatuated and so in love, I let it go, even though the tabloids seemed determined to rub my face in it.

‘When NSYNC went to London in 2000, photographers caught him with one of the girls from All Saints in a car.

‘But I never said anything. At the time we’d only been together for a year. 

‘Another time, we were in Vegas, and one of my dancers who’d been hanging out with him told me he’d gestured toward a girl and said, “Yeah, man, I hit that last night.”

‘I don’t want to say who he was talking about because she’s actually very popular and she’s married with kids now. I don’t want her to feel bad.

‘There were rumours about him with various dancers and groupies. I let it all go, but clearly, he’d slept around. It was one of those things where you know but you just don’t say anything.’

Britney also alleged she became pregnant during their relationship and got an abortion.

She said Justin was ‘so sure that he didn’t want to be a father’ and she wouldn’t have ended the pregnancy if the choice was ‘left up to her alone.’ 

In recent years, the Mirrors hitmaker has shown regret for his past treatment of Britney and publicly apologised to her in 2021 following the release of the FX and Hulu documentary, Framing Britney Spears.

‘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,’ he wrote in a statement. 

Janet Jackson ‘Nipplegate’ 

It has been twenty years since Justin came under fire after he ripped off part of Janet Jackson’s Alexander McQueen costume, exposing her right breast as his Super Bowl halftime performance in Texas.  

140 million viewers were watching at the time.  

The incident turned into a he-said-she-said and it marked the decline of Janet’s career, saw Justin escape relatively unscathed. 

The singer was blacklisted from the industry, with her singles and music videos banned from television and radio airwaves.

In addition to her career almost careening to a full stop, Janet was forced to apologise for the incident on a major media tour. 

It wasn’t until the release of The New York Times documentary Framing Britney Spears in 2021  the topic was brought to light again.

It spurred Justin to issue a public apology to both women.

He said in the note: 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.’

 Justin added, ‘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.’

Although things between the two legendary music artists are smoothed over now, in 2006 Janet told Oprah she felt Timberlake had ‘left her hanging to a certain degree.’

She expressed feeling that ‘all the emphasis was put on me as opposed to us.’

In one part of her documentary, however, the Hollywood vet revealed, ‘We talked once and [Justin] said, “I don’t know if I should come out and make a statement.”‘

 Janet said. ‘And I said, “Listen, I don’t want any drama for you. They’re aiming all of this at me.” So I said, “If I were you, I wouldn’t say anything.”‘

Struggle with NSYNC fame 

Justin skyrocketed into the spotlight after he joined the boyband NSYNC in 1995 as their lead singer. 

But the hitmaker soon began to struggle with the immense pressure – and by the time he parted ways with the group in 2002, he was not shy about the fact that he enjoyed illicit substances to escape. 

He confessed to ‘getting plastered’ and ‘doing his fair share of drugs’ in secret, and he even admitted that he believed he may get arrested one day for it.

‘I’ve never been arrested… though that’s not to say I won’t,’ said the popstar at the time.

‘I’m just like everyone else, I get completely plastered, I’ve done my fair share of drugs and I’ve been caught with my pants down. I just make sure there are no cameras around.’

By the late 2000s, however, it had seemed that Justin had put his wild ways behind him to become a family man instead; he wed Jessica in 2012 and welcomed their son, Silo, together in 2015.