He dominated pop culture at the turn of the 21st century – but it seems Justin Timberlake‘s questionable actions have finally caught up with him.

The singer, 42, reportedly fears being ‘cancelled’ following the release of Britney Spears‘ highly anticipated memoir The Woman In Me, according to The Mirror.

In her book, the pop icon, 41, claims she had an abortion, aged 19, because Justin ‘wasn’t ready’ to be a father – before accusing him of cheating on her with a celebrity and ending their three-year relationship with a text message.

It’s not been an easy couple of years for Timberlake, whose controversial 2004 Super Bowl performance with Janet Jackson was also revisited in recent times following the release of the FX and Hulu documentary, Framing Britney Spears. 

Faced with the backlash, Timberlake issued a public apology to both Janet and Britney for ‘missteps’ during his career that he admitted contributed to ‘a system that condones misogyny and racism’.

But it’s not only his unchecked past that is catching up with him, his present appears to be just as troublesome; in 2019, the actor was caught holding hands with his co-star Alisha Wainwright while hanging out together in New Orleans.

He dominated pop culture at the turn of the 21st century – but it seems Justin Timberlake ‘s questionable actions have finally caught up with him. Pictured with Britney Spears

Reputation expert Eric Schiffer recently said Britney has portrayed her ex as a ‘giant con’ who he claims benefitted from playing a ‘phony victim’ in the aftermath of their split.

‘Britney’s book lacerates Justin’s legacy, and his “good guy” image now appears like it was a giant con,’ he told DailyMail.com exclusively.

‘The public hates inauthenticity, and this bombshell report creates a smoking crater on his reputation and legacy.’

Reflecting on the lasting impact this could have on Justin’s career, the PR expert continued: ‘The backlash Justin faces has just started. You can expect to see a growing, seething anger from Britney fans – and Justin’s, who could sever their emotional connection with the singer.’

Since facing the backlash, Timberlake has seemingly instead tried to ensure headlines are dominated with news of his reunion with NSYNC, as well as rumours of new solo music and a tour.

But has the former pop prince done enough to avoid being cancelled? Here, FEMAIL charts the singer’s fall from grace – and the steps he’s taken to try and regain fans.

BRITNEY SPEARS’ ALLEGATIONS

The way they were: When Britney began dating wholesome NSYNC star Justin Timberlake in 1999 — fans all over the world saw them as America’s golden couple (pictured in 2002)

Britney Spears and Justin Timberlake together in 2002

Britney acrimoniously split from Timberlake in 2002 amid increasing rumours that she had been unfaithful.

Justin appeared to bolster the narrative with his 2002 hit Cry Me a River in which he sings: ‘You don’t have to say, what you did / I already know, I found out from him / Now there’s just no chance / For you and me.’

The singer even went so far as to hire a Britney look-a-like for the music footage. He apparently warned his ex that he was releasing a ‘controversial’ video.

Britney released her highly anticipated memoir The Woman In Me on October 24

She told Rolling Stone in 2003: ‘I think I was in shock, to be honest. I didn’t know what to say, what to do. That was the last thing I ever thought somebody might do. I was really shocked s**tless. But you live and you learn.

‘He got what he wanted. I think it looks like such a desperate attempt, personally. But that was a great way to sell the record. He’s smart,’ she told the outlet at the time.

In her memoir, the Toxic singer writes about that period in time and describes the video as ‘a woman who looks like me cheats on him and he wanders around sad in the rain.’

She went on to write that the media attention the video received turned her into a ‘harlot who’d broken the heart of America’s golden boy,’ when she was actually ‘comatose in Louisiana‘ nursing a broken heart while Timberlake was ‘happily running around Hollywood,’ Variety reported.

While Britney has taken the heat, with it once being assumed she was the one who cheated on Justin, he actually cheated on her on more than one occasion, she claims in her memoir.

The mother-of-two has confessed to cheating on her ex by kissing her choreographer Wade Robson in a bar – but she also hinted that Justin was unfaithful on multiple occasions – including with a celebrity whose identity she has refrained from exposing.

History: Britney and Justin dated from 1999-2002 after they both became child stars when they starred in the Mickey Mouse Club back in the early nineties

Claims: Britney Spears has accused Justin Timberlake of cheating on her during their three-year relationship

The Oops!…I Did It Again singer wrote that the What Goes Around Comes Around hitmaker was photographed with ‘one of the girls from All Saints‘ in London in 2000 and also bragged to one of her backup dancers about a girl he hooked up with in Las Vegas.

The Toxic hitmaker also detailed the ‘agonizing’ decision to terminate the pregnancy in her memoir – after conceiving in late 2000 when the pair were both 19, DailyMail.com can confirm.

The star claimed that while she wanted the baby and ‘dreamed of having a family’ with Timberlake, he ‘wasn’t ready’ for the responsibilities of parenthood and thought the pair were too young.

She writes: ‘It was a surprise, but for me, it wasn’t a tragedy. I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I’d anticipated.

‘He said we weren’t ready to have a baby in our lives, that we were way too young. I’m sure people will hate me for this, but 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. And yet Justin was so sure that he didn’t want to be a father.’

The star said the abortion was ‘one of the most agonizing things I have ever experienced in my life’ in the memoir.

Timberlake hasn’t been kind when it comes to rehashing his relationship with Spears over the years.

During a 2003 interview with Barbara Walters on 20/20, the journalist asked him if Britney had ‘kept her promise to wait to have sex until marriage’. Justin immediately burst out laughing.

A few years later, in 2006, he told journalist Robert Haskell: ‘If I was writing an article about [Britney], I would not be able to fight the urge to write every dirty thing about her.’

In recent years, Justin 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.

He issued an apology to both his ex – and music icon Janet Jackson – for ‘missteps’ during his career that he admitted contributed to ‘a system that condones misogyny and racism’.

‘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.’

Months later, he went on to show support for Britney amid her battle to put her 13-year conservatorship to an end. She was placed into the guardianship by her father, Jamie Spears, in 2008.

In 2021 Justin apologised to Britney for his past treatment of her amid pushback from documentaries made during the #FreeBritney movement

At the height of the #FreeBritney movement, Justin tweeted: ‘No one should ever be held against their will… or ever have to ask permission to access everything they’ve worked so hard for.’

Speaking on behalf of himself and his wife, Jessica, he then added: ‘Jess and I send our love, and our absolute support to Britney during this time. We hope the courts, and her family make this right and let her live however she wants to live.’

The NSYNC frontman has reportedly refrained from contacting Britney to voice his upset at the recent fall out – the stress of which is said to have blighted his wedding anniversary celebrations with wife Jessica.

‘Justin has not reached out to Britney at all about any of this and he is not going to because there is nothing he can say to her,’ a source close to the Toxic singer told DailyMail.com exclusively. ‘She was there and is just telling it from her point of view.

‘That does not mean he is okay with it. Justin is not at all happy about what has come out in this book.’

They added: ‘Doing this book has given Britney life and she really doesn’t care who is offended by anything in it because it is what happened. She was there and lived through it. No one can say anything. She has got this all out of her and is moving on now.’

However in her social media statement last Friday, Britney expressed her dismay at the way The Woman In Me is being perceived.

‘My book’s purpose was not to offend anyone by any means !!! That was me then … that is in the past !!!’ she exclaimed. ‘I don’t like the headlines I am reading … that’s exactly why I quit the business 4 years ago !!!’

Britney maintained: ‘Most of the book is from 20 years ago … I have moved on and it’s a beautiful clean slate from here !!! I am here to establish it that way for the rest of my entire life !!! Either way this is the last of it and s*** happens !!!’

The Oops!…I Did It Again hitmaker reflected: ‘This is actually a book I didn’t know needed to be written … although some might be offended, it has given me closure on all things for a better future !!! Hopefully I can enlighten people who feel particularly alone in most cases or hurt and misunderstood !!!’

She doubled down: ‘Again, my motive for this book was not to harp on my past experiences which is what the press is doing and it’s dumb and silly !!! I have moved on since then !!! #TheWomanInMe’.

JANET JACKSON’S SUPER BOWL ‘WARDROBE MALFUNCTION’

During their infamous 2004 Super Bowl performance, Timberlake ripped off Janet Jackson’s costume and exposed her breast in a scandalous incident that has been dubbed ‘Nipplegate’

During their infamous 2004 Super Bowl performance, Timberlake ripped off Janet Jackson’s costume and exposed her breast in a scandalous incident that has been dubbed ‘Nipplegate.’

Jackson’s career was damaged over the incident, despite the fact that the flesh-exposing incident followed the line ‘Bet I’ll have you naked by the end of this song,’ from Timberlake’s song Rock Your Body.

Following the scandal, her videos and songs were blacklisted from all Viacom owned stations including MTV, VH1 and all the radio stations under their umbrella.

Additionally her invitation to present at the 46th Annual Grammy Awards was rescinded and she was reportedly pressured into skipping the ceremony all together with some calling her a ‘disgraced flash dancer.’

Timberlake on the other hand was allowed to attend, even snagging two awards for Best Male Pop Vocal Performance and Best Pop Vocal Album, also getting an invitation to perform at the Super Bowl in 2018.

When asked about the incident in various interviews, Timberlake chalked it up to a ‘wardrobe malfunction’ while telling Access Hollywood in 2004, ‘Hey man, we love giving y’all something to talk about.’

He seemed to change his tune quickly calling the incident ‘regrettable’ and ‘not intentional,’ taking some level of blame for it in 2007 when he told MTV: ‘In my honest opinion now… I could’ve handled it better.

‘I probably got 10 percent of the blame, and that says something about society. I think that America’s harsher on women … And I think that America is, you know, unfairly harsh on ethnic people.’

He also apologised in 2009 to Entertainment Weekly saying: ‘I wish I had supported Janet more. I am not sorry I apologized, but I wish I had been there more for Janet.’

His latest apology over both the Spears and Jackson incidents came after the Framing Britney Spears documentary. He wrote: ‘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.’

He owned up to using the ‘heartbreak’ of his relationship with Spears to promote his music and garner publicity, after playing up rumours that she had cheated on him.

He wrote: ‘I’ve seen the messages, tags, comments and concerns and I want to respond. I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out o f 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 a system that condones misogyny and racism. I also feel compelled to respond, in part, because everyone involved deserves better and most importantly, because this is a larger conversation that I wholeheartedly want to be a part of and grow from…

‘The industry is flawed. It sets men, especially white men, up for success. It’s designed this way. As a man in a privileged position I have to be vocal about this. Because of my ignorance, I didn’t recognize it for all that it was while it was happening in my own life but I do not want to ever benefit from others being pulled down again.

‘I have not been perfect in navigating all of this throughout my career. I know this apology is a first step and doesn’t absolve the past. I want to take accountability for my own missteps in all of this as well as be part of a world that uplifts and supports.

‘I care deeply about the well-being of the people I love and have loved. I can do better and I will do better.’

Some fans were taken aback by Timberlake’s attempts to combine apologies to Janet and Britney.

The All For You singer never publicly addressed his apology. However, she did post a black heart on a social media post from the singer Tinashe who called her and Britney ‘literally my two biggest idols in the whole universe’ while acknowledging the apology.

DYLAN FARROW BLASTS TIMBERLAKE FOR FAILING TO CONDEMN WOODY ALLEN

Justin Timberlake and Jessica Biel attend The 75th Annual Golden Globe Awards at The Beverly Hilton Hotel on January 7, 2018 in Beverly Hills, California

In 2018, Timberlake once again hit the headlines for all the wrong reasons when Dylan Farrow implied the singer was a hypocrite for working with Woody Allen while being a supporter of a campaign to end sexual assault.

Dylan, Allen’s adoptive daughter, has long claimed the esteemed director and comic abused her when she was seven.

No charges have ever been brought against Allen, who has always denied the claims and said Dylan had been ‘coached’ to make the accusations by her ‘angry’ mother, Mia Farrow, after the couple split up.

But Dylan attacked Timberlake for ‘praising’ Allen while being an ‘activist’.

Timberlake had innocently asked his followers: ‘Random question: Can someone please explain the saying, “You just want your cake and to eat it too.” What else am I about to do with a cake??’

Farrow then replied: ‘The saying means, for example, you can’t support #TIMESUP and praise sexual predators at the same time.

‘You can’t retain your credibility as an activist (i.e. – retain the cake) and, at the same time, praise a sexual predator (i.e. – eating the cake).’

Her message appeared to be a reference to Timberlake’s decision to star in Allen’s 2017 movie ‘Wonder Wheel’, implying the actor and singer should have turned down the job and condemned the director based on Dylan’s claim.

Timberlake has previously shown his support for Time’s Up, including by wearing one of the campaign’s pins alongside an all-black outfit at the Golden Globes ceremony.

But he was criticised for tweeting ‘DAMN, my wife is hot!’ alongside a picture of Jessica Biel before the event.

‘I never molested my daughter’: Woody Allen’s statement in full refuting Dylan Farrow’s claims

‘When this claim was first made more than 25 years ago, it was thoroughly investigated by both the Child Sexual Abuse Clinic of the Yale-New Haven Hospital and New York State Child Welfare.

They both did so for many months and independently concluded that no molestation had ever taken place. Instead, they found it likely a vulnerable child had been coached to tell the story by her angry mother during a contentious breakup.

Dylan’s older brother Moses has said that he witnessed their mother doing exactly that – relentlessly coaching Dylan, trying to drum into her that her father was a dangerous sexual predator. It seems to have worked – and, sadly, I’m sure Dylan truly believes what she says.

But even though the Farrow family is cynically using the opportunity afforded by the Time’s Up movement to repeat this discredited allegation, that doesn’t make it any more true today than it was in the past. I never molested my daughter – as all investigations concluded a quarter of a century ago.’

PICTURED HOLDING HANDS WITH HIS CO-STAR

Timberlake was caught holding hands with actress Alisha Wainwright on November 21 2019 while hanging out together on the balcony at The Absinthe House on Bourbon Street in New Orleans

Justin Timberlake and Jessica Biel started dating in 2007 and soon became one of the most high-profile couples in Hollywood.

They got engaged shortly afterwards during a holiday in Montana, in December 2011, and were married the following year in 2012. The couple welcomed their first child, son Silas, in April 2015.

But they found their relationship making headlines for the wrong reasons in 2019.

The performer was caught holding hands with actress Alisha Wainwright on November 21 while hanging out together on the balcony at The Absinthe House on Bourbon Street in New Orleans.

Approaching midnight, Justin was seen reaching over and clutching the arm of the stunning actress, before she tenderly rested her hand on his right knee.

The singer seemed to place his arm around Alisha in a video shot around the same time. The pair then gripped each other’s hands tightly as they sat chatting and drinking.

The actor, who has been married to Biel since 2012, was not wearing his wedding ring in the photos as he hung out with Wainwright, 30.

Timberlake and Wainwright play on-screen lovers in Palmer, which follows an ex-convict who befriends a boy from a troubled home.

Timberlake apologised in a statement and admitted that he had a ‘lapse in judgment’, before insisting that, ‘nothing happened between me and my co-star.’

‘I drank way too much that night and I regret my behaviour. I should have known better. This is not the example I want to set for my son,’ Timberlake said.

‘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.’

Timberlake and his wife went on to welcome their second son Phineas in 2020.

NSYNC REUNION

NSYNC members attend the 2023 MTV Video Music Awards at Prudential Center on September 12, 2023 in Newark, New Jersey

Comeback: The band’s last single was released a little over two decades ago with the 2002 track, Girlfriend, featuring Nelly; seen in 2001 in NYC

Amid the renewed reaction to Timberlake’s apparent treatment of Britney during and after their relationship, the singer was seemingly ensuring a new topic hit headlines in the form of a NSYNC reunion.

The group – which includes Timberlake, JC Chasez, 47, Joey Fatone, 46, Lance Bass, 44, and Chris Kirkpatrick, 51 – first teased new music while reuniting at the 2023 MTV Video Music Awards.

They then officially dropped their new single titled Better Place – their first in over two decades – in September and fans jumped to social media with emotional reactions in response to the upbeat track.

Better Place is found on the soundtrack for the animated sequel called Trolls Band Together – which was released on November 17.

Upon listening to the song, NSYNC fans flocked to X, formerly known as Twitter, to express their excitement.

One penned, ‘Listening to the new NSYNC song and crying yes I’m fine why do you ask,’ while another added, ‘How many times will I listen to @NSYNC Better Place?!’ followed by a meme from Mean Girls that read, ‘The limit does not exist.’

One social media user wrote, ‘Yes childhood unlocked. Manifesting a reunion tour!’ while a fan typed, ‘listening to jc chasez in 2023 sing a new nsync song just changed many lives (mine).’

NSYNC previously sent fans into a frenzy when they reunited at the 2023 MTV Video Music Awards where they presented Taylor Swift with the award for Best Pop Video – who had expressed shock when she saw the boy band take the stage together.

They had reunited in the past during their performance at the 2013 VMAs as well as in 2018 for the band’s Hollywood Walk Of Fame induction ceremony.

Forbes noted: ‘If “Better Place” performs well on the charts and becomes a hit, it could open a lot of doors for Timberlake. All it takes is one successful song to change some people’s minds, and it could set his next chapter up for a win.

‘Using NSYNC to turn the tables on his public perception could be the best way to reintroduce himself to the masses, and with some luck, the reunion may put him back on top.’

In September, Page Six reported that ‘Justin is coming out with a new album, so he’s planning a big US tour for 2024,’ according to one music insider.