Justin Timberlake's biggest controversies: From 'Nipplegate' to Britney Spears and his drink driving arrest

 (Jordan Strauss/Invision/AP)
(Jordan Strauss/Invision/AP)

Justin Timberlake has sparked a slew of headlines this week after he was arrested for driving under the influence of alcohol in upstate New York on Monday.

But it isn’t the first time the 43-year-old singer has found himself at the epicentre of media frenzy.

After rising to fame as a Disney Mouseketeer and one fifth of boyband NSYNC, Timberlake cemented his status as a major star of the 2000s after going solo.

Initially known for his squeaky-clean image, his reputation has since been marred by a series of controversies and scandals in recent years.

The Standard take a look at them:

Britney Spears’ memoir claims


Britney Spears recounted her rocky relationship with Timberlake, who she dated from 1999 to 2002, in her memoir The Woman In Me.

Their time together was dogged by rumours of infidelities on both sides - and Timberlake only fanned the flames further when he released his solo single, Cry Me A River, in 2002.

The US singer continued to fuel speculation when a model, who bore a striking resemblance to Spears, portrayed an unfaithful partner in the song’s music video, leaving Spears’ to feel like she was “a harlot who’d broken the heart of America’s golden boy”.

Yet, Spears’ book told a different story.

She acknowledged cheating on Timberlake "one time" when she kissed a backing dancer but said he had been unfaithful "a couple of times" during their relationship.

Not only that but she discussed the “difficult” decision to have an abortion at his insistence after learning she was pregnant in 2000.

She wrote: “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, but Justin definitely wasn’t happy about the pregnancy. He said we weren’t ready to have a baby in our lives, that we were way too young.”

She added: “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.”

Janet Jackson and ‘Nipplegate’

 (AFP via Getty Images)
(AFP via Getty Images)

In 2004, viewers witnessed what could easily go down in history as the most buzzworthy halftime show ever, famously dubbed “Nipplegate”.

The impressive musical lineup included Janet Jackson, Kid Rock, P. Diddy, Nelly, and Justin Timberlake in Houston.

As the halftime extravaganza reached its peak, Jackson and Timberlake turned up the heat with a rendition of Timberlake's 2003 smash hit, Rock Your Body, but Timberlake accidentally yanked off a piece of Jackson's costume, revealing a bit more than anticipated.

This incident prompted criticism from the FCC head Michael Powel, who condemned it as a “celebration tainted by a classless, crass, and deplorable stunt”. While CBS, who broadcast the event, were fined a record $550,000.

While many details surrounding the incident remain unclear, the FCC's subsequent investigation led to Congress passing legislation aimed at increasing fines for “indecency” on television.

In the aftermath, Jackson's career stalled due to the backlash, while Timberlake managed to avoid facing similar consequences and proceeded to headline the Super Bowl halftime show himself in 2018.

Reflecting on the scandal in 2018, he told Beats 1: “I stumbled through it, to be quite honest.

“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.”

Cheating allegations

Justin Timberlake and Jessica Biel are celebrating their 10th wedding anniversary (PA Archive)
Justin Timberlake and Jessica Biel are celebrating their 10th wedding anniversary (PA Archive)

Timberlake was forced to apologise to his wife Jessica Biel in 2019 after he was photographed holding hands with his Palmer co-star Alisha Wainwright in New Orleans.The Mirror singer previously had endured reports that he had a “three-day fling” with Olivia Munn in 2010, two years before their wed.

However, seven years after they tied the knot and while Biel was expecting their second son, Timberlake was pictured looking cosy with Wainwright.

After the photos were published, he publicly apologised to his actress wife, citing that he “displayed a strong lapse in judgement” and blamed drinking too much. He wrote on Instagram at the time: “I stay away from gossip as much as I can, but for my family I feel it is important to address recent rumors that are hurting the people I love.

“A few weeks ago I displayed a strong lapse in judgment – but let me be clear – nothing happened between me and my co-star.

“I drank way too much that night and I regret my behavior. I should have known better. This is not the example I want to set for my son,” he continued.

“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.

“This was not that.”

DWI arrest


Timberlake was charged early on Tuesday with drunken driving after police said he ran a stop sign and veered out of his lane in a village in New York's Hamptons on Monday night.

The boy band singer-turned-solo star and actor was driving a 2025 BMW in Sag Harbour around 12.30am when an officer stopped him and determined he was intoxicated, according to a court document.

"His eyes were bloodshot and glassy, a strong odour of an alcoholic beverage was emanating from his breath, he was unable to divide attention, he had slowed speech, he was unsteady afoot and he performed poorly on all standardised field sobriety tests," the court papers said.

Timberlake told the officer he had one martini and was following some friends home, according to the documents.

After being arrested and taken to a police station in nearby East Hampton, he refused a breath test, said the court papers, which listed his occupation as "professional" and said he's "self-employed".

The Grammy winner was released without bond later on Tuesday morning after being arraigned in Sag Harbor.

He was charged with a driving-while-intoxicated misdemeanor, and his next court date was scheduled for July 26, the Suffolk County district attorney's office said.

Edward Burke Jr., a local lawyer representing Timberlake, declined to comment on Tuesday other than to confirm the star doesn't need to appear in person for his next court date. Timberlake's California-based representatives didn't return multiple requests for comment on Tuesday.

However, the officer who arrested Timberlake for drink driving had no idea who the singer was when he took him into custody, a source has said.

The police officer “was so young that he didn't even know” who the 10-time Grammy winner was and “didn't recognise him or his name,” a source told Page Six.

The 43-year-old whispered “this going to ruin the tour” during the arrest, a separate source told the celebrity news site.

When pressed on what tour he was talking about, Timberlake said “the world tour,” according to the source.