6 of Justin Timberlake's Biggest Scandals Before His DWI Arrest: From Britney Spears Drama to Nipplegate and More

Justin Timberlake and Britney Spears dated from 1999 to 2002, but their relationship was tumultuous.

After ending things, Timberlake released the track "Cry Me a River," which sparked rumors that the "Toxic" singer cheated on him. He also cast a Spears look-alike for the music video.

On the other hand, Spears released her memoir, The Woman in Me, in which she accused the "Mirrors" singer of cheating on her multiple times.

In the same memoir, Spears shocked her fans when she wrote about her pregnancy and subsequent abortion. She claimed Timberlake was unhappy about it and told her he was not ready to have a baby.

“I’m sure people will hate me for this, but I agreed not to have the baby. I don’t know if that was the right decision. 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," she wrote.

Timberlake started his career as the founding member of *NYSNC with JC Chasez, Joey Fatone, Chris Kirkpatrick and Lance Bass. In 2002, he released his debut solo album, Justified, which reportedly caused the band's disbandment.

*NSYNC initially announced their hiatus in 2002 after their Celebrity Tour, but they officially split in 2004.

“We were on a stadium tour, and I just felt like the whole thing was too big,” Timberlake told The Hollywood Reporter in 2017. “It started as a fun snowball fight that was becoming an avalanche. And, also, I was growing out of it.”

He added, “I felt like I cared more about the music than some of the other people in the group. And I felt like I had other music I wanted to make and that I needed to follow my heart."

Janet Jackson headlined the 2004 Super Bowl halftime show and plotted a performance that featured Timberlake and other artists. When they performed "Rock Your Body," he ripped off a piece of her costume, exposing part of her chest.

MTV and Timberlake released statements after the incident, while Jackson addressed what happened in a separate post the following day.

"The decision to have a costume reveal at the end of my halftime show performance was made after final rehearsals," said Jackson. "MTV was completely unaware of it. It was not my intention that it go as far as it did. I apologize to anyone offended — including the audience, MTV, CBS and the NFL."

The Federal Communications Commission launched an investigation into the performance after receiving more than half a million complaints from the viewers.

Years after the performance, Timberlake issued his first direct apology statement to Jackson following the release of the Framing Britney Spears documentary.

Timberlake made headlines for allegedly cheating on Jessica Biel before and after their marriage.

In 2010, Us Weekly released a report alleging the "Can't Stop the Feeling!" hitmaker cheated on his then-girlfriend with Olivia Munn. They reportedly started a fling after meeting at a MySpace event, but Timberlake dismissed the allegations all at once.

Years later, he was pictured canoodling with his Palmer costar, Alisha Wainwright, at a bar in New Orleans. At the time, Timberlake reportedly went out without wearing his wedding ring and “appeared to have been drinking heavily and was unsteady on his feet.”

They also held hands at one point.

Timberlake penned a since-deleted Instagram post to apologize to everyone and his family.

“A few weeks ago, I displayed a strong lapse of judgment — but let me be clear — nothing happened between me and my co-star,” he said. “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.”

Part of his statement also read, “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.”

On Monday, June 17, Timberlake was pulled over and arrested after running a stop sign and failing to drive in his lane. Police in Sag Harbor, N.Y., revealed the "Selfish" singer operated his 2025 BMW "in an intoxicated condition."

In the official complaint, Timberlake reportedly told the police he "only had one martini" at the time. He also refused to undergo a chemical test thrice.

A Sag Harbor Village Police Department officer also disclosed how Timberlake "had slowed speech, he was unsteady afoot and he performed poorly on all standardized field sobriety tests.”

He was released without bail afterward. He was ordered to virtually appear before the court on July 26.