Justin Timberlake’s major scandals over the years: DWI, Nipplegate, Britney Spears drama, more
Since stepping into the spotlight over three decades ago, Justin Timberlake has faced his fair share of controversies over the years.
From being arrested for DWI-related charges to an unforgettable performance dubbed “Nipplegate,” keep scrolling for a list of the singer’s most headline-making scandals.
Britney Spears Drama
Timberlake was 18 when he struck up a romance with pop star Britney Spears after the two initially met on set of “The All-New Mickey Mouse Club.”
Although the young couple was beloved by fans and Hollywood alike, things took a sour turn when their relationship fizzled out three years later.
The singer suggested in his 2002 hit song “Cry Me a River” that Spears had cheated on him – even using a Spears look-alike to portray a cheating ex in the track’s accompanying music video at the time.
Two decades later, the “Toxic” singer flipped the script on Timberlake when she accused him of cheating on her a “couple” of times in her tell-all memoir, “The Woman In Me.”
Abortion Reveal
Elsewhere in Spears’ memoir, she claimed she secretly got an abortion at the request of Timberlake, who “didn’t want to be a father.”
“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,” Spears wrote.
“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.”
Spears admitted that she still thinks about the “agonizing” decision to this day.
Amid backlash from the “Gimme More” singer’s memoir, Timberlake seemingly shaded her at one of his concerts, telling fans he wanted “to apologize to absolutely f–king nobody.”
Janet Jackson Super Bowl Halftime Show
Timberlake sparked backlash again in 2004 after he exposed Janet Jackson’s right breast while performing together during the Super Bowl XXXVIII Halftime Show.
Although the nudity was shown for less than one second, over 140 million people were watching at the time, which resulted in a whopping 540,000 complaints to the FCC.
Timberlake later claimed the incident — dubbed “Nipplegate” — was “unintentional.” He did not face any consequences.
Meanwhile, Jackson’s career took a serious hit afterward. In 2021, the “Selfish” singer apologized to Spears and Jackson, both of whom he admittedly “failed.”
Infidelity Rumors
Timberlake allegedly cheated on now-wife Jessica Biel in 2010 with Olivia Munn.
At the time, an insider told Us Weekly that Timberlake met Munn at a party in New York City and “started chasing her immediately.” The pair were allegedly seen being “openly affectionate” at a hotel.
However, reps for Timberlake strongly denied the report.
Nine years later, he was spotted getting cozy with “Palmer” co-star Alisha Wainwright at a bar — despite still being married to Biel.
The two were photographed holding hands during a night of drinking. At one point, the actress was seen placing her hand on Timberlake’s knee.
Soon after, Timberlake took to Instagram to issue an apology to Biel and assure fans that “nothing happened” with Wainwright – despite his “strong lapse of judgment” that night.
“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],” he wrote.
“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.”
DWI Arrest
In June 2024, Timberlake was arrested on charges of DWI in Sag Harbor, NY. A source told Page Six at the time that the “Trolls” voice actor was pulled over after having dinner with friends at the historic American Hotel.
Although Timberlake insisted he only had “one martini,” police alleged that his “eyes were bloodshot and glassy” and that “a strong odor of an alcoholic beverage was emanating from his breath.”
According to the criminal complaint, Timberlake “was unable to divide attention, he had slowed speech, he was unsteady afoot, and he performed poorly on all standardized field sobriety tests.”
When asked to be breathalyzed, we’re told the singer refused and was taken into custody.
He was arrested on one count of driving while intoxicated and cited for two traffic violations: running a stop sign and failing to stay in his lane. Timberlake has yet to address the incident and a rep for the singer did not immediately respond to Page Six’s requests for comment.
