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When Justin Timberlake stepped out of a court in Long Island on Tuesday (June 18) morning, having been arrested for driving while intoxicated the previous night, the Prince of Pop will have known his time in custody had already sparked headlines around the world.

It’s far from the first time the 43-year-old singer and actor has found himself at the center of a media storm. After first rising to fame as a Disney Mouseketeer, Timberlake formed NSYNC alongside JC Chasez, Lance Bass, Joey Fatone and Chris Kirkpatrick. They quickly became one of the biggest boybands in the world, with Timberlake dating fellow pop icon Britney Spears and pursuing a solo career that made him one of the major stars of the 2000s.

Initially, the former member of The All New Mickey Mouse Club had a squeaky-clean reputation, but that’s long since been tarnished by a string of controversies and scandals. Here’s a rundown:

Encouraging Britney Spears to have an abortion, then dumping her by text

Timberlake’s three-year relationship with Britney Spears made them the royal couple of pop in the late 1990s and early 2000s, but their time together was dogged by rumors of infidelities on both sides. When Timberlake released his cheating-themed 2002 solo single “Cry Me A River”, he played into these stories by appearing in the video with a model who resembled Spears acting unfaithfully. Spears later said she felt as if she’d been portrayed as “a harlot who’d broken the heart of America’s golden boy”.

Spears’ 2023 memoir The Woman In Me told a different story. While she admitted to cheating on Timberlake “one time” by kissing a backing dancer, she added that “there were a couple of times during our relationship when I knew Justin had cheated on me”. She also revealed that she had gone through with an abortion at his urging, writing: “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: “I agreed not to have the baby. I don’t know if that was the right decision.”

Britney Spears with Timberlake at the Hollywood premiere of her movie ‘Crossroads’ in 2002. (Kevin Winter/Getty Images)
Spears also revealed that Timberlake broke up with her with a two-word text: “It’s over”.

Sparking ‘Nipplegate’ with Janet Jackson at the Super Bowl

During Janet Jackson’s halftime show at the 2004 Super Bowl in Houston, Texas, Timberlake appeared as a surprise guest and the pair performed a duet of his hit “Rock Your Body”. When he reached his final line (“Bet I’ll have you naked by the end of this song”), Timberlake pulled off a part of Jackson’s costume to reveal her right breast, which was adorned with a sun-shaped nipple shield.

Janet Jackson and Timberlake performing at the 2004 Super Bowl (Getty Images)
The moment was onscreen for less than a second, but sparked a massive uproar. CBS, who broadcast the event, were fined a record $550,000. The search for footage of the incident has been cited by the creators of YouTube as a key moment that inspired them to create the site. Jackson’s career suffered in the aftermath, but Timberlake received much less backlash and went on to headline the Super Bowl halftime show himself in 2018. That year, he told Beats 1 about his reaction to the scandal: “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 rumours

Jessica Biel with husband Timberlake in 2022 (Getty Images)
Timberlake first met actor Jessica Biel on a night out in 2007. The couple married in 2012, but only after surviving reports of Timberlake’s “three-day fling” with Olivia Munn in 2010. Then in 2019, Timberlake publicly apologized to Biel after he was pictured holding hands with his Palmer co-star Alisha Wainwright in New Orleans. “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,” Timberlake wrote on social media. “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. 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

On the night of June 17, Timberlake was arrested in the wealthy Hamptons enclave of Sag Harbor, Long Island for driving while intoxicated. Police told TMZ that the star was at the American Hotel partying and blew through a stop sign when he left. Cops started to follow him, and pulled him over after he started swerving.

He failed a field sobriety test and reportedly refused a breathalyzer. Officers said they observed Timberlake with glassy eyes and smelled alcohol on his breath. He appeared in a Long Island court on Tuesday and was released without bail. He is due back in court on July 26.