Justin Timberlake’s Biggest Scandals: DWI, Cheating

Justin Timberlake has found himself in hot water on more than one occasion throughout his nearly three decade career. The “SexyBack” singer’s biggest scandals include an arrest for DWI, a cheating scandal and a Super Bowl nip slip controversy.

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Sag Harbor PD/MEGA

DWI Arrest

In June 2024, Justin was arrested after leaving a party in Sag Harbor, New York. The former boybander was pulled over around 12:30 am on June 18 after officers watched him run a stop sign and swerve between lanes.

Justin refused a breathalyzer and failed a field sobriety test, TMZ reported. He was arrested and released hours later without bail.

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Justin Timberlake’s Biggest Scandals Through the Years: DWI, Cheating

Super Bowl

During his halftime performance as part of Super Bowl XXXVIII, Justin ripped off part of Janet Jackson’s outfit, flashing her breast on live television.

While Janet was banned from performing in subsequent Super Bowls, Justin returned to the iconic stage in 2018. CBS was fined more than half a million dollars by the Federal Communications Commission (FCC) for airing the NSFW moment.

“I am sorry if anyone was offended by the wardrobe malfunction during the halftime performance at the Super Bowl,” he said following the incident. “It was not intentional and is regrettable.”

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Brit’s Claims

Following his split from Britney Spears in the early 2000s, Justin released his hit song “Cry Me a River,” leading fans to believe the “Sometimes” artist cheated on the former boybander.

However, nearly 20 years later, Britney alleged in her memoir The Woman in Me that it was Justin who cheated on her before ending their relationship.

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Britney’s Conservatorship Scandal

After a documentary about Britney’s 13-year conservatorship called Framing Britney Spears premiered in 2021, Justin came under fire for his prior treatment of his ex.

“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,” Justin wrote in his Instagram apology at the time. “I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism.”

He continued, “I specifically want to apologize to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed.”

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Cheating

Justin was caught packing on the PDA with his Palmer costar Alisha Wainwright in December 2019. The duo were spotted getting touchy at a bar in New Orleans while the “Bye Bye Bye” singer was married to wife Jessica Biel.

“A few weeks ago, I displayed a strong lapse of judgment — but let me be clear — nothing happened between me and my costar,” Justin wrote via Instagram following the incident. “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.”