The complicated 'falling upwards' of Justin Timberlake.

In August 2002, Justin Timberlake performed at the MTV Video Music Awards, where he premiered his debut solo single for the first time.

Singing 'Like I Love You', the moment marked the beginning of the singer's successful, enduring solo career after a stint on The All-New Mickey Mouse Club show as a child and years of fame with boy band NSYNC.

He was from that performance, a solo star.

Watch: Justin Timberlake and Zane Lowe on the Janet Jackson SuperBowl incident. Post continues below video.

What followed was years of popularity, dozens of singles, a film career and a number of controversies, after which he always emerged unscathed. But finally, in the past year or two, Timberlake's reputation has taken a series of knocks as people re-evaluate the treatment of celebrities, especially in relation to women and minorities.

The shine of Timberlake, now 42, has worn off, leaving an uncomfortable tale of a man who continually succeeded off the back of other's losses.

A reframing of Timberlake's story entered the mainstream after New York Times' documentary, Framing Britney Spears, delved into the treatment of his ex-girlfriend during the 90s and 2000s.

Now, a similar thing is happening again. And this time it is thanks to Spears' own words, following the release of her memoir The Woman in Me. The book recounts her early life, career and of course, the 13-year conservatorship she was finally freed from in November 2021.

But another thing that is clear from the book is that Timberlake will always be part of Spears' story. 

The pair — the lead singer of one of the most popular boy bands in the world and world's biggest popstar — were as close to royalty as it got in America when they dated from 1999-2002. They were the very definition of pop royalty, and the media attention was immense.

It was also very different for both of them.

In footage from Framing Britney Spears, we see Spears being asked about her virginity at a press conference. Her body and her sex life were tabloid fodder and water cooler topics at the time. Meanwhile, Timberlake mostly avoided talking about their relationship until 2002, after their breakup and while he was launching his solo career.

Britney Spears and Justin Timberlake in February 2002, one month before they broke up. Image: Getty. 

Spears and Timberlake had first met as kids on The All-New Mickey Mouse Club and began a relationship as he was part of one of the world's most popular boybands, and she began the Princess of Pop. Throughout her book, Spears writes much about her infactuation and devotion to her then-boyfriend, who she lived with in Florida.

But it was far from the fantasy we were sold.

We now know from Spears' memoir that they pushed aside multiple instances of cheating in the relationship, many involving him and one involving her, and tellingly, she felt like he pulled back when he began working on this solo music.

"When Justin began making his first solo album, Justified, he started being very standoffish with me," she recalled. "I think that was because he decided to use me as ammunition for his record, and so it made it awkward for him to be around me, staring at him with all that affection and devotion."

Unsurprisingly, his biggest single of this period directly addressed their 2002 split. In 'Cry Me A River', Timberlake sings about the end of their relationship and in the video, he cast a Spears look-a-like.

Spears later said she was blindsided by the video. She felt the song gave an unfair depiction of her, but said Timberlake was a clever marketer. He knew that'd sell records, and he was right.

In The Woman in Me, Spears described the video turning her into a "harlot who'd broken the heart of America's golden boy," when she was actually "comatose in Louisiana" with a broken heart while he was "happily running around Hollywood".

In an interesting passage, Spears wrote that she believed Timberlake — and NSYNC, as a whole — "tried too hard" to fit in with Black artists at their peak. She recalled a cringeworthy moment in which Timberlake altered his speech, using what is known as a "blaccent", when meeting R&B musician Ginuwine.

"Fo-shiz fo-shiz what's up homie!" she recalled him saying.

After their breakup, the 'Cry Me A River' video controversy landed Timberlake a radio interview for the Star and Buc Wild Morning Show. An urban contemporary show, it was a space Timberlake would never have found himself during his boy band days and he clearly enjoyed being there.

It was here he was asked: "Did you f*** Britney Spears?"

Timberlake laughed, initially indicating he wasn't going to answer. Pressed again, he gave in: "OK, I did it," to cheers from the hosts.

With Spears' memoir, we now know plenty more context. Publicly, Spears persona as an innocent (read: virginal) young pop star was a key part of her 'brand'. She wrote about feeling disturbed by this in her memoir.

"My managers and press people had long tried to portray me as an eternal virgin; never mind that Justin Timberlake and I had been living together; and I'd been having sex since I was 14," she shared.

"Why did my managers work so hard to claim I was some kind of young-girl virgin even into my 20s? Whose business was it if I'd had sex or not?"

Unfortunately, what this public persona did do was allow Timberlake to lean into the coolness factor of corrupting sweet, innocent Spears. And it did him wonders.

The misogyny is perfectly laid out on the cover of Details magazine, which touted Justin as a man who can be forgiven for his "sissy music" because he "got into Britney's pants". Gross.

Image: Details.

At the time, no one really batted an eyelid. This was, unfortunately, indicative of the culture in 2002. 

In 2004, the now infamous "wardrobe malfunction" during Timberlake's Super Bowl performance with Janet Jackson took place.

Timberlake apologised for this. Doing so was allegedly part of an agreement with the Recording Academy to allow him to be onstage to accept his Grammy awards that year, but we don't even need hindsight to realise this was underwhelming. 

"I know it's been a rough week on everybody," he said, smirking. "What occurred was unintentional, completely regrettable, and I apologise if you guys were offended."

He gave no mention of Jackson, who had faced an onslaught of negative press after the show. She was fined and blacklisted by US radio and MTV, while Timberlake's career continued to go from strength to strength.

There was a long period during the mid-late 2000s where it was impossible to avoid Timberlake's music, and the Super Bowl invited him back to perform the Halftime Show in 2018.

For years, Timberlake was presented opportunities and each time, a win was as guaranteed as it can be in a fickle place like Hollywood.

As we entered the 2010s, Timberlake was involved in a series of gaffes, which included imitating Rihanna's mother's Bajan accent while accepting an award in 2013 and dedicating his 2017 #TimesUp/#WhyWeWearBlack IG post to his "hot wife".

Image: Getty.

Each time, the internet stirred - but only a little.

Then in 2019, Timberlake was photographed holding hands with his Palmer co-star Alisha Wainwright while his wife Jessica Biel was pregnant with their second child.

After a few days of speculation, Timberlake apologised to Biel (but not Wright) in an Instagram post, blaming his "lapse in judgement" on drinking "way too much".

In 2021, as the world watched in horror at how Spears was treated during Framing Britney Spears, Timberlake's name trended on Twitter for days at a time.

With the reframing of Spears' story, he found himself facing a much more critical lens.

He had released some bangers, but he was also a man who appeared to have spring-boarded a solo career out of sl*t-shaming an ex-girlfriend, and who had not once shown empathy for the woman who faced all the consequences of a 'wardrobe malfunction' he caused.

Timberlake had been given opportunities and second chances where others have not been so lucky.

The privilege of Justin Timberlake was right there for all to see, and we were finally looking at it properly.

In February 2021, Timberlake addressed both Spears and Jackson in a public apology.

"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," he wrote.

"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."

He said he was ignorant of his privilege in Hollywood and no longer wanted to benefit from others being pulled down.

"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," he wrote.

During a May 2021 battle on DJ battle web series Versuz, between rapper and producer Swizz Beatz and frequent Timberlake collaborator Timbaland, Swizz claimed Timberlake had profited off of Black culture throughout his music career - which has become a full circle conversation following Spears' comments about Timberlake's attempts to fit in with Black musical artists.

Hip-hop and R&B heavily influenced Timberlake's music, especially on his first couple of records, and it's a sentiment many Black creators have shared before.

For those looking for receipts. pic.twitter.com/EBLw92l6P4

— Ernest Owens (@MrErnestOwens) February 13, 2021

"He gotta admit that he loves the Black culture and he gotta be on this stage," Swizz told Timbaland. "You took from the Black culture, you give to the Black culture. Come to Verzuz and be a part of the Black culture."

He later clarified that he had no problem with Timberlake, but the conversation had already progressed elsewhere, with many fans upset Timberlake had been invited to the show before a number of Black creators - including Janet Jackson.

And now, with the release of The Woman in Me, and a series of fresh bombshells about Timberlake's relationship with Spears — including allegations that he cheated regularly, encouraged her to get an abortion when she accidentally fell pregnant, and ultimately that he dumped her by text — it's all happening again tenfold.

Though unverified, of course, 'insiders' have claimed that Timberlake is unhappy with the details Spears shared in the book. Unfortunately for him, it became the biggest selling celebrity memoir of all time in less than a day. And he, despite a recent NSYNC reunion at the MTV VMAs and a new song for the upcoming Trolls movie, has no way near the platform he once did.

And so once again, the world is looking at Timberlake through a different lens.

For 20 years, he emerged from scandals with barely a mark. In 2023, it's finally caught up with him.

This article was originally published in June 2021 and has been updated.

Feature image: Getty.