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.

READ MORE: Britney Spears to get ‘25% of The Woman In Me’s net profits’ following $12.5million advance – after tome became ‘highest selling celebrity memoir in history’ on FIRST day of release

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.