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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 Spearsβ 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 β even during accusations of cheating.
Most recently, Timberlake was arrested for a DWI in the Hamptons on June 18. 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 Timberlakeβs biggest controversies from over the years.
1999 to 2002: Dating Britney Spears
Timberlake and Spears, both βAll New Mickey Mouse Clubβ stars, began dating in 1999 but ultimately ended things in 2002.
After their breakup, Timberlake released his hit song βCry Me a River,β which insinuated that Spears cheated on him.
Years later, Timberlake supported Spears when sheΒ spoke out in open court for the first time in 2021Β about her βabusiveβΒ 13-year conservatorship, which hasΒ since ended.
But in 2023, Spears leveled a number of accusations against her ex-boyfriend in her memoir βThe Woman in Me,β including that Timberlake was the one who was unfaithful in their relationship.
Spears said that Timberlake cheated with βanother celebrity,β but she didnβt reveal the starβs identity because she βnow has a familyβ and Spears βdoesnβt want to embarrassβ them.
The βStrongerβ singer also claimed thatΒ she had an abortion when the exes were togetherΒ because Timberlake was reportedly not ready to be a father.
βI loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than Iβd anticipated,β wrote Spears. βBut Justin definitely wasnβt happy about the pregnancy. He said we werenβt ready to have a baby in our lives, that we were way too young.β
After Spearsβ memoir came out, she issued an apology to Timberlake and shouted out his song βSelfish.β In response, Timberlake declared that heΒ wanted to apologize to βabsolutely f β β king nobodyβ 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.
The group disbanded partly because Timberlake wanted to be a solo artist.
βWe were on a stadium tour, and I just felt like the whole thing was too big,β Timberlake told the Hollywood Reporter in 2017. βIt started as a fun snowball fight that was becoming an avalanche. And, also, I was growing out of it.β
βI 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,β he added.
Timberlake became a huge independent star after leaving *NSYNC. As of June 2024, heβs dropped six studio albums with hit songs including βRock Your Body,β βWhat Goes Around β¦ Comes Around,β βSuit & Tie,β βMirrorsβ and βCanβt Stop the Feeling.β Heβs headlined five tours, including the ongoing Forget Tomorrow World Tour.
The superstar has won 10 Grammys out of 39 nominations.
Timberlake has also starred in movies including βThe Social Network,β βFriends with Benefits,β βWonder Wheelβ and βReptile.β He does voice acting in the βTrollsβ movies.
*NSYNC reunited at the 2023 MTV Video Music Awards and at one of Timberlakeβs concerts in Los Angeles in March 2024. They also released the song βBetter Placeβ for βTrolls 3β in 2023, marking their first group song in 22 years. They did another song together, βParadise,β for Timberlakeβs 2024 album βEverything I Thought It Was.β
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 Spearsβ memoir came out. Bass told TMZ that Timberlake deserves βforgivenessβ for what happened in his relationship with Spears.
2004: βNipplegateβ
βNipplegateβ 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 βwardrobe malfunctionβ was βnot intentional and is regrettable.β
The FCC investigated the incident and fined CBS $550,000, but it was later voided by the US Court of Appeals.
The scandal bruised Jacksonβs career and her ego, while Timberlake came out of it relatively unscathed.
Jacksonβs initial apology for the incident read, βThe 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 β including the audience, MTV, CBS and the NFL.β
Timberlakeβs apology read, βI 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.β
Timberlake laterΒ issued a direct apology to Jackson in 2021, saying that he βfailedβ the βAll for Youβ singer.
Jackson discussed βNipplegateβ in her 2022 documentary βJanet.β
βHonestly, 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 thatβs got to stop,β she said of the incident.
βJustin and I are very good friends, and we will always be very good friends,β she continued. βWe spoke just a few days ago. He and I have moved on, and itβs time for everyone else to do the same.β
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.
Timberlakeβs rep denied the allegations at the time. Munnβs 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 βPalmerβ co-star Alisha Wainwright in New Orleans in November 2019.
The Sun obtained exclusive videoΒ and photos of the pair hanging out at the bar. Sources claimed that Timberlake was not wearing his wedding ring and βappeared to have been drinking heavily and was unsteady on his feet.β
Timberlake later apologized for the incident in a now-deleted Instagram post.
βA few weeks ago, I displayed a strong lapse of judgment β but let me be clear β nothing happened between me and my co-star,β he said. βI 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.β
He continued: βI 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.β
Biel stayed quiet during the controversy.
A source told PEOPLE at the time that Biel βbelieves he didnβt cheat on her.β They added, βWhatβs most important to her in life is her family and being the best mom to Silas. Sheβll never break up her family over something like this.β
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.
βThis guy is a mega star and heβs one of the most recognizable faces. I thought he was incredible in this movie,β she said. βYouβd be surprised how someone is in character. You can take away all the noise and just focus on whatβs in front of you like, βLetβs make a movie.β β
2024: DWI arrest
Timberlake was arrested on DWI charges in the HamptonsΒ 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.
PerΒ Page Six, Timberlake was βwith a bunch of friendsβ 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 βone martiniβ and he refused their request to take a breathalyzer test. Sources said the musician appeared glassy-eyed and smelled of alcohol.
βHis friends were telling the police, βLet him go, let him go,ββ an insider told the outlet. The cop who pulled Timberlake over was also reportedly βso young that he didnβt even knowβ who the star was.
The source added: βHe didnβt recognize him or his name.β
βThis is going to ruin the tour,β Timberlake allegedly told the officer.
The cop responded, βWhat tour?β
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 driverβs license will also be suspended in New York.
Two days before the arrest, Biel celebrated Timberlake with a Fatherβs Day post via Instagram.
βYouβre 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,β she wrote. βWe LOVE YOU πͺ¨β€οΈ.β
Hours before the scandal, Biel was also photographed filming the upcoming Prime Video thriller series βThe Better Sisterβ in Central Park.