Justin Timberlake’s biggest controversies: DWI arrest, Britney Spears’ cheating allegations, Nipplegate and more

What goes around, comes around.

Justin Timberlake has been at the center of multiple controversies throughout his storied career that began when he was a child.

As a teenager, Timberlake had a tumultuous relationship with Britney Spears that made headlines again in 2023 when Spears’ book came out.

His wife, Jessica Biel, with whom he shares sons Silas, 9, and Phineas, 3, has stood by the singer throughout his public issues — even during accusations of cheating.

Most recently, Timberlake was arrested for a DWI in the Hamptons on June 17. He was charged with driving while intoxicated and cited for running a stop sign and failure to keep in his lane.

Here are are Justin Timberlake’s biggest controversies from over the years.

1999 to 2002: Dating Britney Spears

Timberlake and Spears, both “All New Mickey Mouse Club” stars, began dating in 1999 but ultimately ended things in 2002.

After their breakup, Timberlake released his hit song “Cry Me a River,” which insinuated that Spears cheated on him.

Years later, Timberlake supported Spears when she spoke out in open court for the first time in 2021 about her “abusive” 13-year conservatorship, which has since ended.

But in 2023, Spears leveled a number of accusations against her ex-boyfriend in her memoir “The Woman in Me,” including that Timberlake was the one who was unfaithful in their relationship.

Spears said that Timberlake cheated with “another celebrity,” but she didn’t reveal the star’s identity because she “now has a family” and Spears “doesn’t want to embarrass” them.

The “Stronger” singer also claimed that she had an abortion when the exes were together because Timberlake was reportedly not ready to be a father.

“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,” wrote Spears. “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.”

After Spears’ memoir came out, she issued an apology to Timberlake and shouted out his song ‘Selfish.” In response, Timberlake declared that he wanted to apologize to “absolutely f–king nobody” during a concert in NYC.

2002: Leaving *NSYNC

Timberlake was a founding member of *NSYNC with Lance Bass, Joey Fatone, Chris Kirkpatrick and JC Chasez.

In April 2022, the group disbanded partly because Timberlake wanted to be a solo artist.

“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.”

“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,” he added.

Timberlake became a huge independent star after leaving *NSYNC. As of June 2024, he’s dropped six studio albums with hit songs including “Rock Your Body,” “What Goes Around…Comes Around,” “Suit & Tie,” “Mirrors,” and “Can’t Stop the Feeling.” He’s headlined five tours, including the ongoing The Forget Tomorrow World Tour.

The superstar has won 10 Grammys out of 39 nominations.

Timberlake has also starred in movies including “The Social Network,” “Friends with Benefits,” “Wonder Wheel” and “Reptile.” He does voice acting in the “Trolls” movies.

*NSYNC reunited at the 2023 MTV Video Music Awards and at one of Timberlake’s concerts in Los Angeles in March 2024. They also released the song “Better Place” for “Trolls 3” in 2023, marking their first group song in 22 years. They did another song together, “Paradise,” for Timberlake’s 2024 album “Everything I Thought It Was.”

Despite leaving the group, Timberlake has seemingly stayed close with the other *NSYNC members. Bass, 45, even defended Timberlake when he was getting hate after Spears’ memoir came out. Bass told TMZ that Timberlake deserves “forgiveness” for what happened in his relationship with Spears.

2004: “Nipplegate”

“Nipplegate” was the viral incident with Timberlake and Janet Jackson at the 2004 Super Bowl.

Jackson suffered an onstage mishap when Timberlake grabbed her leather top and accidentally exposed her breast in front of 140 million viewers. Timberlake later claimed that the “wardrobe malfunction” was “not intentional and is regrettable.”

The FCC investigated the incident and fined CBS $550,000, but it was later voided by the U.S. Court of Appeals.

The scandal bruised Jackson’s career and her ego, while Timberlake came out of it relatively unscathed.

Jackson’s initial apology for the incident read, “The decision to have a costume reveal at the end of my halftime show performance was made after final rehearsals. 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.”

Timberlake’s apology read, “I am sorry if anyone was offended by the wardrobe malfunction during the halftime performance at the Super Bowl. It was not intentional and is regrettable.”

Timberlake later issued a direct apology to Jackson in 2021, saying that he “failed” the “All for You” singer.

Jackson discussed “Nipplegate” in her 2022 documentary “Janet.”

“Honestly, this whole thing was blown way out of proportion. And, of course, it was an accident that should not have happened, but everyone is looking for someone to blame and that’s got to stop,” she said of the incident.

“Justin and I are very good friends, and we will always be very good friends,” she continued. “We spoke just a few days ago. He and I have moved on, and it’s time for everyone else to do the same.”

2010: Cheating allegations

In October 2010, Us Weekly reported that Timberlake cheated on his then-girlfriend Biel with Olivia Munn.

A source told the outlet that Timberlake and Munn had a three-day fling after meeting at a MySpace event.

Timberlake’s rep denied the allegations at the time. Munn’s rep never commented on the claims.

2019: Canoodling with his co-star

Seven years into his marriage with Biel, Timberlake was caught canoodling with his “Palmer” co-star Alisha Wainwright in New Orleans in November 2019.

The Sun obtained exclusive video and photos of the pair hanging out at the bar. Sources claimed that Timberlake was not wearing his wedding ring and “appeared to have been drinking heavily and was unsteady on his feet.”

Timberlake later apologized for the incident in a now-deleted Instagram post.

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

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.”

Biel stayed quiet during the controversy.

A source told PEOPLE at the time that Biel “believes he didn’t cheat on her.” They added, “What’s most important to her in life is her family and being the best mom to Silas. She’ll never break up her family over something like this.”

Wainwright never directly addressed her behavior with Timberlake, but she did praise the Grammy Award winner in an interview with Entertainment Tonight over a year later.

“This guy is a mega star and he’s one of the most recognizable faces. I thought he was incredible in this movie,” she said. “You’d be surprised how someone is in character. You can take away all the noise and just focus on what’s in front of you like, ‘Let’s make a movie.’ “

2024: DWI arrest

Timberlake was arrested on DWI charges in the Hamptons early in the morning on June 17.

He was pulled over in Sag Harbor and taken into custody, and was cited for running a stop sign and failure to keep in his lane. The following day, he appeared in court and was released without bail.

Per Page Six, Timberlake was “with a bunch of friends” at the American Hotel on Main Street before he drove off around 12:30 a.m. The hotel is a 2-minute walk from the local police station and rooms can run up to $625 a night.

Timberlake reportedly told the police that he only had “one martini” and he refused their request to take a breathalyzer test. Sources said the musician appeared glassy-eyed and smelled of alcohol.

“His friends were telling the police, ‘Let him go, let him go,’” an insider told the outlet. The cop who pulled Timberlake over was also reportedly “so young that he didn’t even know” who the star was.

The source added: “He didn’t recognize him or his name.”

“This is going to ruin the tour,” Timberlake allegedly told the officer.

The cop responded, “What tour?”

Timberlake has been on his Forget Tomorrow World Tour since April.

Per court documents, his next court appearance will be July 26, but he does not have to attend in-person. His driver’s license will also be suspended in New York.

Two days before the arrest, Biel celebrated Timberlake with a Father’s Day post via Instagram.

“You’re so many things to so many people. But to us you are THE ROCK. The rock we climb on, we lean against. The rock that shades us from the sun. And when we recline on you, as we always do, hopefully our butts will keep you eternally grounded and warm,” she wrote. “We LOVE YOU 🪨❤️.”

Hours before the scandal, Biel was also photographed filming the upcoming Prime Video thriller series “The Better Sister” in Central Park in New York City.