Justin Timberlake has weathered many storms throughout his career in the spotlight.
After getting his start on Star Search and The All New Mickey Mouse Club, Timberlake formed ‘NSync alongside MMC costar JC Chasez, Lance Bass, Joey Fatone and Chris Kirkpatrick. During the group’s heyday, lead singer Timberlake sparked a romance with Britney Spears.
Spears and Timberlake’s relationship only lasted three years but ended bitterly over reports of infidelity. Timberlake’s solo song “Cry Me a River” even alluded to claims that Spears had been unfaithful.
“We’re not perfect. I don’t judge anybody,” Timberlake told Barbara Walters in 2002. “It’s just young love. It was a very intense relationship, that’s for sure.”
Related: Justin Timberlake Through the Years: From ‘Star Search’ to Grammy Winner
Spears was shell-shocked that Timberlake accused her of cheating before flipping the script on him in her memoir, The Woman in Me. (A source told Us Weekly in October 2023 that Timberlake was “trying to distance himself” from the book’s bombshells.)
Keep reading for a break-down of Timberlake’s biggest controversies and scandals, from cheating drama to Nipplegate:
Encouraging Britney Spears to Have an Abortion
Spears alleged in her The Woman in Me book that she became pregnant during her relationship with Timberlake, per an excerpt published by People.
“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,” the “Baby One More Time” singer wrote, claiming she decided to terminate the pregnancy because Timberlake wasn’t ready to become a father. “If it had been left up to me alone, I never would have done it.”
After Spears went through with the procedure, Timberlake allegedly attempted to comfort her by playing his guitar.
Britney Spears Cheating Claims
Timberlake dropped his song “Cry Me a River,” which he wrote in two hours, less than one year after he and Spears split. (Spears claimed in her memoir that Timberlake ended their romance via text.) In the music video, Timberlake costarred alongside a model, who looked like Spears, as she acted out a cheating scene.
Spears, who was vocal about her dislike of the video, later alleged in The Woman in Me that Timberlake was actually the one who cheated on her a “couple” of times.
No Longer In Sync
‘NSync disbanded in April 2002 as Timberlake wanted to go solo.
“I was growing out of it,” he told The Hollywood Reporter in a February 2017 profile. “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 continued: “We were on a stadium tour, and I just felt like the whole thing was too big. It started out as a fun snowball fight that was becoming an avalanche.”
Super Bowl Nipplegate
Timberlake sparked controversy in the middle of his Super Bowl XXXVIII halftime performance when he ripped off part of Janet Jackson’s costume, exposing her right breast. CBS, who broadcast the Super Bowl, was fined $550,000 by the Federal Communications Commission (FCC) and barred Jackson from returning to the stage. Timberlake, for his part, issued an apology, noting his actions were “unrehearsed” and “unintentional” but did not face any consequences.
Timberlake issued a second apology for not speaking up via Instagram in February 2021.
Cheating on Jessica Biel
Amid his romance with now-wife Biel, Us Weekly confirmed that he had been unfaithful. A source exclusively told Us in October 2010 that Timberlake had a three-day fling with Olivia Munn. Timberlake’s rep strongly denied the allegations at the time and Munn’s spokesperson did not issue a comment.
Timberlake and Biel were able to work through their issues, getting married in 2012. They later welcomed sons Silas and Phineas.
Related: Justin Timberlake and Britney Spears' Cheating Claims in Their Own Words
Packing on the PDA With His Palmer Costar
While filming Palmer in New Orleans, Timberlake was spotted holding hands with his costar Alisha Wainwright at a bar in December 2019. The photos also showed Wainwright placing her hand on his knee. A source subsequently told Us that the costars were “just friends” and “nothing inappropriate” occurred.
Timberlake then issued a public statement. “A few weeks ago, I displayed a strong lapse of judgment — but let me be clear — nothing happened between me and my costar,” he wrote via Instagram. “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 [Silas].”
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He added: “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.”
Check the Credits
‘NSync released their first new song in 20 years, “Better Place,” in September 2023 to accompany Timberlake’s animated film Trolls Band Together. Eagle-eyed fans quickly noticed that the track was credited as “‘NSync featuring Justin Timberlake,” wondering why Timberlake received preferential treatment. (No members of the band addressed the credit drama at the time.)
DWI Arrest
Us confirmed in June 2024 that Timberlake had been arrested for driving while intoxicated in the Hamptons. Police took the singer into custody for DWI-related charges in Sag Harbor, New York. Neither Timberlake nor Biel spoke out immediately following the arrest. He was arraigned the day after his arrest and released without bail. TMZ reported that he was charged with one DWI count for running a stop sign and failing to stay in his lane. Another court date was scheduled for July 2024.
