WITH bloodshot glassy eyes, the “Prince of Pop” looked almost unrecognisable in a mugshot released by police.
The SexyBack singer was arrested for suspected drink-driving in The Hamptons, NY, in the early hours of Tuesday.
Police reported Timberlake ran a stop sign, swerved into another lane and smelt of booze.
With his world tour just underway, timing could not be worse for the former squeaky-clean Disney star.
Now, insiders fear his arrest could be a damaging blow to his already fragile marriage to Jessica Biel, who looked tense and downcast as she appeared in public yesterday.
With dark circles etched under her eyes, the 42-year-old actress looked broken while filming scenes in New York for her upcoming Amazon series, The Better Sister.
“Jessica will be colossally disappointed and embarrassed that once again, Justin is in the headlines for all the wrong reasons,” a source said.
“There’s going to be a lot of questions asked of Justin moving forward, without a doubt.
“He clearly has this self-destructive streak that keeps rearing its head.
“Jessica has shown the patience of a saint forgiving his various misdeeds over the past few years but this is really testing her patience and then some.
“It’s well known that their marriage has been on the brink for some time.
“But he’s gone and screwed up again, which is going to affect everyone in his world, not just him.”
The pair have weathered many storms in recent years, not least when Justin was photographed holding hands on a night out in New Orleans with co-star Alisha Wainwright in 2019.
The 42-year-old singer apologised to his wife and two kids, for a “strong lapse in judgement” and blamed booze for his behaviour.
“He had a lot of work to do in order to win her trust again after that scandal,” explained the source.
“And to his credit that’s something he managed to pull off by changing his lifestyle and focusing on becoming a better version of himself.
“They moved away from Los Angeles and settled in Montana, went to therapy and he swore up and down he’d never embarrass her or put their marriage in jeopardy again.”
But the couple faced more turmoil from damaging revelations in Britney Spears‘ recent memoir, The Woman In Me.
In her candid book, Britney, 43, revealed that she got pregnant with Timberlake’s baby when she was 19 during their three-year relationship, and he encouraged her to have an abortion.
She wrote: “Justin didn’t want to be a father…I agreed not to have the baby. I don’t know if that was the right decision. If it had been left up to me alone, I never would have done it.”
She also revealed that Timberlake cheated on her with “another celebrity” and she “turned a blind eye”.
Even though they parted ways more than two decades ago, she said she’s been “under a curse” since their break-up.
Before the book’s release last year, multiple sources told how Justin was “concerned” about its contents. “He’s very curious what she’ll reveal from their relationship,” one alleged.. “It’s eating at him.”
When news of his arrest spread and his mugshot began circulating online, Britney appeared to take a veiled jab at her ex with a cryptic post.
Taking to Instagram, she shared a snap of a fruity looking cocktail and mysteriously told her followers: “It’s the little things you know [flower emojis].”
Alongside his personal life challenges, music industry insiders believe Timberlake has faced difficulties due to underwhelming sales of his sixth solo album, Everything I Thought It Was.
One insider said: “It hasn’t been the smash hit he’d been hoping for.
“It’s been difficult for an artist of his stature to realise he’s now past his prime – his glory days are behind him.”
A second source added: “It can’t be easy for him to deal with audience rejection and coming to terms with the fact that music tastes have moved on.”
The first single from the album – Selfish – was released in January and peaked at number 19 on the US Billboard Hot 100.
The album, his first since 2018’s Man in the Woods, was released in March and debuted at number four on the US Billboard 200 but soon slipped down the charts.
Music critics gave the album mixed reviews, with one flaming it as a “rehash of past glories”.
The lacklustre reviews and disappointing sales are a stark contrast to his glory days when Timberlake dominated the charts.
He shot to fame as a Disney Mouseketeer before forming NSYNC with JC Chasez, Lance Bass, Joey Fatone, and Chris Kirkpatrick. The group quickly became one of the best-selling boy bands of all time and helped shape the boy band phenomenon of the late 1990s and early 2000s
Their self-titled debut album, “NSYNC”, was released in 1997. It included hits like “Tearin’ Up My Heart” and “I Want You Back”.
The album achieved multi-platinum status.
NSYNC embarked on several successful tours, including the “No Strings Attached Tour” and the “PopOdyssey Tour”.
Timberlake’s high-profile relationship with fellow pop star Spears and his successful solo career cemented his status as a major star in the noughties.
The pair first met as kids when they both joined the cast of The Mickey Mouse Club, a popular children’s show on the Disney Channel.
Justin Timberlake has dated many women over the years...
Danielle Ditto – A childhood romance Justin allegedly lost his virginity to. “He is sweet, gentle and thoughtful. It was almost like he was trained to be the perfect gentleman,” she said in 2003.
Veronica Finn – Dated the American singer and actress for a year in 1997, as he was getting famous with N*Sync
Fergie – The Black Eyed Peas star confessed she and Justin used to “have fun and make out” after releasing hit single Where Is The Love together.
Britney Spears – Dated from 1999 to 2002 at the height of their careers. He originally said they ended after she cheated on him, but in her memoir, Britney claimed he cheated on her first and encouraged her to get an abortion while they were together.
Tonya Mitchell – The singer Justin allegedly cheated on Britney with.
Alicia Keys – Linked to the If I Ain’t Got You singer in 2002 – but never officially dated.
Jenna Dewan – Briefly dated in 2002 when she was his backing dancer.
Tatyana Ali – He casually dated the Fresh Prince of Bel-Air actress in 2003.
Cameron Diaz – He dated The Mask actress from 2003 to 2007, until Jessica Biel turned his head soon after.
Their friendship blossomed on set, along with other future stars like Christina Aguilera and Ryan Gosling.
When Justin and Britney announced they were dating in 1999, they were hailed as pop’s golden couple.
The pair split three years later amid reports she was unfaithful to him.
Timberlake fuelled these rumours with his hit song “Cry Me a River”.
While it doesn’t directly say Britney cheated, its lyrics hint at her betrayal.
In her recent memoir, Spears wrote about how she felt voiceless after her ex put out the hit, which effectively put forward his narrative of being the wronged party in their breakup.
“I felt there was no way at the time to tell my side of the story,” she wrote. “I couldn’t explain, because I knew no one would take my side once Justin had convinced the world of his version.
“I don’t think Justin realised the power he had in shaming me. I don’t think he understands to this day.”
Timberlake later dated actress Cameron Diaz and pop star Fergie before marrying Jessica in 2012. The couple then welcomed two sons, Silas, aged 9, and Phineas, aged 4, who they prefer to keep out of the public spotlight.
Talking about how special his wife is to him, Timberlake later said: “She is the single-handedly most significant person in my life.
At the height of his fame in 2004, the dad of two faced a backlash for sexism over “nipplegate”.
During the halftime show at the Super Bowl in Houston, he surprised the audience by performing “Rock Your Body” with Janet Jackson.
I specifically want to apologise to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed.
Justin Timberlake
At the song’s climax, he pulled off part of Jackson’s costume, revealing her right breast adorned with a sun-shaped nipple shield, coinciding with the line, “Bet I’ll have you naked by the end of this song.”
The risqué move sparked an uproar, with the broadcasting network CBS fined $550,000 (£430,000) and Jackson’s career dealt a damaging blow.
That year, Timberlake told Beats 1 about his reaction to the scandal: “I stumbled through it, to be quite honest.
He said: “I had my wires crossed and it’s just something that you have to look back on and go like, OK, well you know, you can’t change what’s happened, but you can move forward and learn from it.”
But fans have criticised him for not showing growth from it, and in recent years, Timberlake’s previous behaviour has resurfaced, leading to accusations of being “misogynistic.”
Justin Timberlake hired Sag Harbor legal eagle Ed Burke Jr for his DWI case
Justin’s attorney has represented a gamut of notable names out east.
In 2015, the attorney represented a pre #MeToo era Matt Lauer in his fight with his Water Mill neighbors to plant trees along his property in an effort to combat noise from adjoining properties that were spooking his horses.
In 2017, Ed represented Harvey Weinstein in a fender bender incident in a parking lot in the Hamptons, where the disgraced movie mogul allegedly tried to drive away.
In 2001, he represented Lizzie Grubman, a nightlife publicist whose car careened into a crowd of 16 people in front of a Hamptons club, before fleeing the scene.
In 2021, he finally issued an apology to Britney and Janet in an Instagram post.
It read: “I specifically want to apologise to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed…
“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.”
While Jackson did not specifically refer to Timberlake’s apology, shortly after she expressed her gratitude to fans in a video on social media.
“I was at home just the other day by myself and I began to cry,” she said.
After Timberlake’s shock arrest on Tuesday, insiders are questioning whether he’ll cancel his world tour Forget Tomorrow, which kicked off in April.
He has not issued a statement regarding his arrest or the status of his tour, but he is scheduled to appear in court on July 26.
Insiders believe his top priority will be repairing his marriage. But, the question remains: will Jessica be able to forgive and forget?
“Jessica adores Justin,” continues the source. “She’s desperate for this marriage to be her happily ever after and those loving selfies she posts are very much from the heart.
“But right now he’s in the doghouse again, and for very good reason.”
