“This is going to ruin the tour.” “What tour?” “The world tour”.
It’s safe to say that Justin Timberlake’s alleged interaction with a police officer after his arrest in June on suspicion of drinking and driving is now the stuff of legend. His words may go down as some of the most iconic of his illustrious career, so perfectly they encapsulate the expeditious downfall of the Timberlake brand in the last few years.
The tour in question — The Forget Tomorrow World Tour — is the 43-year-old’s first in five years and was supposed to be something of a comeback. But, as Timberlake touches down in the UK this week as part of the European leg, clearly things aren’t going so smoothly for him.
While JT was once a universally beloved boyband sweetheart and became the king of pop, his name now comes with a heavy helping of baggage.
Until recently, Timberlake had been adjacent to only a host of scandals rather than the focus of press attention afterwards; such as with Janet Jackson and “nipplegate” in 2004, and being papped holding hands with co-star Alisha Wainwright in 2019, while married to Jessica Biel, with whom he has two kids, Silas, 9, and Phineas, 4.
The first sign of the tide turning against the star was the release of the 2021 documentary Framing Britney Spears. This re-examined his relationship with Spears and his contribution to the sexist media campaign against her in the early 2000s. He apologised following internet pressure, but the storm kept coming.
After Spears released The Woman In Me, her highly anticipated memoir last year, which included a litany of stories about Timberlake — including accusing him of serially cheating on her — it highlighted his contribution to toxic noughties’ tabloid culture and its persecution of female celebrities.
And then, on June 18 this year, he was arrested in the Hamptons on suspicion of drinking and driving. His bleary-eyed mugshot was immediately shared thousands of times. Last week, Timberlake was forced to make a virtual appearance in a New York courtroom where he was re-arraigned on a drunk driving charge from the June incident.
Appearing via video link from Antwerp, Belgium, where he performed at the weekend, he pleaded not guilty to one charge of driving while intoxicated. The singer cut a glum figure on screen, speaking only twice to respond to Judge Carl Irace, who suspended him from driving in New York.
The tour though, must go on. This week, Timberlake is set to play four UK dates, including back-to-back shows at London’s O2 arena. As he prepares to take to the stage, we look back on where it all went wrong for the singer.
‘He got what he wanted’ — Cry Me A River and the cheating allegations against Britney Spears
For a while, it seemed that Timberlake was untouchable. When NSYNC’s first album hit the charts in 1998, he was clean-cut, extremely talented and seemingly likeable. In a music era defined by ageing rockstars, his energy, vocal range and slick dance moves set him apart, and he reigned supreme.
Around this time he began dating Britney Spears, and their romance was, for many, the definition of the all-American A-list fairytale. After first meeting as child actors on Disney’s The All-New Mickey Mouse Club House in 1992, Spears was only 17 and Timberlake 18 when their relationship began in 1999.
Their young love story was a constant subject of public fascination (remember the Canadian tuxedos?), which intensified further when they split in 2002.
In March 2002, amid intense speculation about their relationship, Spears reportedly said during a London press conference promoting her film Crossroads that she was not in "an intense relationship with anyone at the moment.” A few days later, she unequivocally told the Big Breakfast show she was single.
And then, in October 2002, Timberlake released the now infamous music video for Cry Me a River, the single from his latest album Justified. The video featured Timberlake trashing the house of an unfaithful girlfriend who bore a distinct resemblance to Spears, confirming the song was inspired by Spears and perpetuated a rumour in the media that she had cheated on Timberlake.
Spears slammed the video as a publicity stunt, telling Rolling Stone: "So he got what he wanted. I think it looks like such a desperate attempt, personally."
But, as was often the case in the early 2000s, public opinion sided with Timberlake, and Spears’ reputation nosedived. In 2006 — no less than four years after their break-up — Timberlake released What Goes Around…Comes Around, which many saw as another dig at Spears. Meanwhile, the Baby One More Time singer was publicly struggling with her second divorce from actor Kevin Federline and sobriety.
Janet Jackson and Super Bowl ‘nipplegate’ scandal
One of Timberlake’s most surreal Teflon moments came in 2004, two years after his break-up with Spears. On Sunday, February 1, Timberlake and Janet Jackson were among several musicians set to headline the Super Bowl’s coveted half-time show. The pair were due to end the set with a rendition of Timberlake’s hit Rock Your Body.
In the final few moments of their performance, as Timberlake sang his last line: “Bet I’ll have you naked by the end of this song,” he tore off part of Jackson’s costume to reveal her breast, with her nipple covered by a sun-shaped shield. The CBS broadcast immediately cut away to a wide shot of the stage.
Despite the moment lasting for less than a second, the fallout was immense, with an MTV executive blaming Jackson — only for another spokesperson to reveal it was a team decision. Jackson's representative explained the incident thus: "Justin was supposed to pull away the rubber bustier to reveal a red lace bra. The garment collapsed and her breast was accidentally revealed."
The scandal, christened “nipplegate”, rumbled on for weeks. Media commentators crucified Jackson: she was set to later perform at the Grammys following the Super Bowl, but the awards show banned her from taking the stage. Her career stagnated, while Timberlake went on to win two Grammys that year.
Speaking to USA Today, Jackson said she felt humiliated but that the outrage was disproportionate. "It's truly embarrassing for me to know that 90 million [140 million] people saw my breast, and then to see it blown up on the Internet the size of a computer screen [...] But there are much worse things in the world, and for this to be such a focus, I don't understand."
Regarding the sustained backlash, she continued: "Who knows... Maybe they'll get mad at something that I do in my show, but at least it won't be new to me, since I've already gone through all of this.”
‘I know I failed’ — Timberlake apologises after Framing Britney Spears documentary
In 2021 after the release of the groundbreaking documentary Framing Britney Spears, the tide started to turn on Timberlake. Although the documentary focused on exploring the #FreeBritney movement and her ongoing conservatorship, fans picked up on a portion of the film that re-examined her relationship with Timberlake. “The way that people treated her, to be very high school about it, was like she was the school sl*t and he was the quarterback,” New York Times critic-at-large Wesley Morris says in the film.
In particular, fans focused on archive clips of Timberlake bragging on live radio about having sex with Spears. At the time of their relationship, Spears said she was waiting until she was married to lose her virginity. But during a radio interview, Timberlake publicly revealed that they had slept together. In response to the question “Did you f**k Britney Spears?” Timberlake laughed before stating, “OK, I did it.”
In a subsequent interview with Barbara Walters, Timberlake laughed when asked if Spears had “kept her promise to wait until marriage” to have sex.
The documentary prompted celebrities such as comedian Sarah Silverman and X/Twitter users to apologise to Spears for how she was endlessly ridiculed in the 2000s (Silverman had roasted the singer at the 2007 VMAs). Fans then swarmed Timberlake’s Instagram comments, demanding that he also publicly apologise to Spears for his role in her public demonisation.
A few days after the documentary’s release, Timberlake did just that. “I have seen the messages, tags, comments, and concerns and I want to respond,” the singer wrote on his Instagram account. “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 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.”
“Fo shiz, fo shiz! Ginuwiiiiiine’ — cringey revelations in Britney Spears’ memoir
When Spears released her 2023 memoir The Woman In Me, Timberlake had been publicly vilified. However, the new revelations from her book only intensified the storm.
One of the most scandalous claims was that Timberlake serially cheated on Spears throughout their three-year relationship.
“There were a couple of times during our relationship when I knew Justin had cheated on me. 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,” she recalls. “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.”
Timberlake allegedly boasted about his affairs, with one involving a now famous woman. “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,’” she continued. “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.”
She also addressed the Cry Me A River music video, claiming that it turned her into a “harlot who’d broken the heart of America’s golden boy,” when in reality she was “comatose in Louisiana” nursing a broken heart and Timberlake was “happily running around Hollywood.”
And then, there were viral cultural appropriation allegations. In the noughties, Timberlake was known to dabble in Black aesthetics, experimenting with street fashion and cornrows. This was referenced in a passage from Spears’ memoir, alleging an interaction between Timberlake and R&B singer Ginuwine which went viral for its “cringey” nature.
“His band 'N Sync was what people back then called ‘so pimp.’ They were white boys, but they loved hip-hop. To me, that’s what separated them from the Backstreet Boys, who seemed very consciously to position themselves as a white group. 'N Sync hung out with Black artists. Sometimes I thought they tried too hard to fit in.”
She recalled a specific incident in New York, where they encountered “a guy with a huge, blinged-out medallion flanked by two giant security guards.”
“J got all excited and said, so loud, ‘Oh yeah, fo shiz, fo shiz! Ginuwiiiiiine! What’s up, homie?’” she writes. Felicia Culotta, Spears’s assistant reportedly mocked Timberlake’s butchered slang by doing an impression of him. “J wasn’t even embarrassed,” Spears said. “He just took it and looked at her like, Okay, f**k you, Fe.”
‘This is going to ruin the tour’ — the infamous drink driving arrest
Timberlake had gone quiet recently, until the early hours of June 18, 2024. The singer was pulled over in Sag Harbor, a village on New York’s Long Island, for allegedly running a stop sign and veering out of the lane while driving his 2025 BMW X7.
When officers stopped him, Timberlake's eyes were "bloodshot and glassy" and a "strong odour of an alcoholic beverage was emanating from his breath", according to a charging document. His speech was slowed and he performed poorly on the officers' sobriety tests, the document said, and he refused a breathlyser test.
Then, an anonymous source for Page Six claims that the arresting officer shared an exchange that sounds almost comically scripted, with Timberlake mumbling that his arrest was going to “ruin the tour.” The officer asked: “What tour?” Timberlake replied: “The world tour.” Cue a litany of memes for the ages.
"I had one martini and I followed my friends home," Timberlake also allegedly told the officer who stopped him, according to the BBC's US partner CBS News.
He was released without bail after being formally charged. Last Friday, Timberlake was re-arraigned on the DWI charge in a virtual court appearance. During the hearing Judge Carl Irace suspended him from driving in New York, citing his refusal to take a breath test during his arrest. Appearing via video link from Antwerp, Belgium, Timberlake again pleaded not guilty to one charge of driving while intoxicated.
A week after the arrest, Timberlake admitted to the crowd at his Chicago concert that: "It's been a tough week.” “I know sometimes I'm hard to love,” he said. “But you keep on loving me and I love you right back.”
Timberlake has previously confessed to abusing substances. Eighteen years before his DWI arrest, he admitted to getting “completely plastered” in an interview in 2006 with Observer Music Monthly.
“I’ve done way too many drugs already. I’ve already inhaled and I’ve already … who knows?” he said. “I’m just like everyone else, I get completely plastered, I’ve done my fair share of drugs and I’ve been caught places with my pants down,” he added. “It’s just I make sure there are no cameras around.”
The cameras will certainly be on him as he takes to the stage in the UK this week.
