Justin Timberlake’s Controversial Moments Throughout His Career: A Timeline

From the Janet Jackson Super Bowl incident to his recent DWI arrest, here’s a look back at the pop star’s controversial moments throughout his career

Justin Timberlake in New York City in June 2019. PHOTO: 

JAMIE MCCARTHY/FILMMAGIC

Justin Timberlake has endured many controversies throughout his prolific career.

During his years in the boy band *NSYNC, the pop star, 43, famously dated Britney Spears — a relationship that was in the spotlight when they were together and again when the “Lucky” singer, 42, released her memoir The Woman in Me in 2023.

Timberlake also was involved in one of the most talked about Super Bowl halftime show performances in history when he infamously ripped off Janet Jackson’s top, exposing her bare breast on live television during their set.

The “Selfish” artist has also been plagued by cheating rumors amid his marriage to Jessica Biel —whom he wed in 2012 and shares sons Silas, 9, and Phineas, 3½ — during which she remained by his side.

Recently, Timberlake was arrested on Long Island on a charge of driving while intoxicated or impaired, which PEOPLE confirmed. He also received two citations: one for running a stop sign and one for failure to keep in lane.

Here’s a timeline of some of Timberlake’s controversies over the years.

April 2002: Timberlake Leaves *NSYNC to Launch Solo Career

In April 2002, Timberlake left *NSYNC to launch his solo career.

In a 2017 cover story with The Hollywood Reporter, he opened up about needing to “follow my heart” in terms of his career. “I was growing out of it. I felt like I cared more about the music than some of the other people in the group,” Timberlake told the outlet.

In an interview with Yahoo Entertainment in 2023, Joey Fatone revealed he was “blindsided” by the “SexyBack” artist’s solo career.

“I was not blindsided by [NSYNC’s breakup],” he told the outlet. “I was more blindsided as far as [Justin] coming out with music and not knowing that he was going to go and do an actual album/tour thing.”

Fatone, 47, added, “It was more of, ‘Hey, I’m going to do some music, and then we’ll get back together.’ That’s what that was.”

*NSYNC. PHOTO BY HULTON ARCHIVE / GETTY IMAGES

November 2002: Justin Timberlake Releases “Cry Me a River” Insinuating Britney Spears Cheating Allegations

In November 2002, Timberlake released the music video for “Cry Me a River”, which famously featured an unfaithful girlfriend that looked similar to his ex-girlfriend Spears. The song was the second single featured on his debut solo album Justified.

In 2003, Timberlake told Teen People that while he wouldn’t say explicitly who his songs were about, they would “bring clarity. They’re explanatory. I don’t have to say it.”

He further discussed the song in his 2018 book Hindsight, which featured more insight into his songwriting process for the track, explaining that his “strong” feelings pushed him to write it in only two hours.

“I’ve been scorned. I’ve been pissed off. That feeling inspired me to write ‘Cry Me a River,’” he wrote.

The song — and the narratives around it — also prompted journalists to grill Spears.

In a famous 2003 interview Diane Sawyer asked her: “He’s going on television and pretty much said you broke his heart, you did something that caused him so much pain, so much suffering. What did you do?”

In her 2023 memoir The Woman in Me, Spears addressed the video and the negative media attention she received at the time.

“May I just say that on his explosive album and in all the press that surrounded it, Justin neglected to mention the several times he’d cheated on me?” she wrote. “There’s always been more leeway in Hollywood for men than for women. And I see how men are encouraged to talk trash about women in order to become famous and powerful. But I was shattered.”

Justin Timberlake, Britney Spears.AXELLE/BAUER-GRIFFIN/FILMMAGIC, DIMITRIOS KAMBOURIS/WIREIMAGE

February 2004: Timberlake and Janet Jackson’s Super Bowl Halftime Show Controversy

2004’s Super Bowl halftime show became one of the most talked-about performances in history.

While Jackson was the headliner that year, Timberlake was the surprise guest. But his surprise appearance became a scandal when he infamously ripped off Jackson’s top, exposing her bare breast on live TV while singing “Rock Your Body.” The pop culture moment became known as “Nipplegate.” Over the years, fingers have been pointed in an attempt to place blame on who’s responsible for the incident.

After the set, Timberlake apologized for the controversy saying “it was not intentional and is regrettable.” MTV also released a statement apologizing and saying it was “unrehearsed, unplanned, completely unintentional.” At the time Jackson’s reps told MTV News that “she apologizes for the incident.”

Days later, Jackson shared her own statement explaining that the “costume reveal” was made after final rehearsals and MTV wasn’t aware of it, apologizing “to anyone offended — including the audience, MTV, CBS and the NFL.”

What followed was an FCC investigation that resulted in CBS, which aired the Super Bowl, a record $550,000 for airing the “wardrobe malfunction.” However, it was later voided by the U.S. Court of Appeals.

After “Nipplegate,” Jackson’s music was also blacklisted by radio and television stations as a result.

Timberlake was blamed by a majority of the public for the incident.

Janet Jackson and Justin Timberlake perform at half-time at Super Bowl XXXVIII at Reliant Stadium on Feb. 1, 2004 in Houston.JEFF HAYNES/AFP VIA GETTY

In 2004, he opened up about the performance during an interview with local TV station KCBS and noted that he was “frustrated at the whole situation,” adding, “I’m frustrated that my character is being questioned and the fact of the matter is, you know, I’ve had a good year, a really good year, especially with my music.”

Before Timberlake’s 2018 headlining Super Bowl performance, he told Apple Music’s Zane Lowe on Beats 1 that he and Jackson had resolved things, adding: “I don’t know that a lot of people know that. I mean, I don’t think it’s my job to do that, because you value the relationships that you do have with people.”

In 2021, he wrote his first direct apology in a lengthy Instagram post to Jackson, following the release of the NYT‘s documentary Framing Britney Spears.

“I specifically want to apologize to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed,” he wrote.

In 2022, Jackson addressed the Super Bowl incident in a tell-all documentary of her own for the first time.

She set the record straight on the pair’s friendship in a message to fans recorded ahead of its release.

“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,” Jackson said.

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

October 2010: Timberlake’s Cheating Rumors with Olivia Munn

In 2010, it was reported that Timberlake had allegedly cheated on then-girlfriend Biel with actress Olivia Munn around the time that the pair had broken up. But a source shot down chatter that he had a fling with the actress.

At the time of their breakup, a source told PEOPLE that “there was never any proof” of infidelity.

A different source who knew the pair said Biel “looked the other way” when it came to Timberlake’s cheating allegations. They said “it’s been a rough road” for the pair who denied rumors of a breakup in 2009 after spending some time apart due to busy work schedules.

November 2019: Hand-Holding Controversy with Alisha Wainwright

While filming the 2021 movie Palmer in New Orleans, Timberlake was seen holding hands with costar Alisha Wainwright in photos and video posted by The Sun.

In the video, Timberlake was seen enjoying drinks with the group. At times Wainwright appeared to rest her hand on his knee. In still images posted to the site, the pair appeared to be holding hands.

However, a source with direct knowledge of the situation said there was nothing to see and that it was “completely innocent.”

“It’s a balcony with a group of people and it was definitely nothing happening,” the insider said. “He’s down there shooting [his film] Palmer, they’re starring in the movie together and they’re cool and everybody was just hanging out.”

A rep for Wainwright denied the rumors saying there was “no validity” to them.

The source added: “The video may look a way, but literally it was nothing. It was some friends, members of the team, crew and people like that. They all know each other and were hanging. Like come on, they’re on an open balcony in New Orleans and he’s famous. It was nothing.”

Justin Timberlake; Alisha Wainwright. SHUTTERSTOCK; GETTY

In early December, Timberlake posted to his Instagram account explaining the situation and apologizing to wife Biel.

“I stay away from gossip as much as I can, but for my family, I feel it is important to address recent rumors that are hurting the people I love.” he wrote at the time.

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

October 2023: Britney Spears Addresses Relationship with Justin Timberlake in Her Memoir

Spears addressed her infamous relationship with Timberlake in her 2023 memoir The Woman in Me.

In it, she revealed she became pregnant with Timberlake’s baby during their relationship but had a medical abortion at their home.

Spears wrote that the pregnancy “was a surprise” but not “a tragedy,” as she was in love with the boy-bander and hoped to eventually have children with him.

“But Justin definitely wasn’t happy about the pregnancy,” she wrote in the book. “He said we weren’t ready to have a baby in our lives, that we were way too young.”

In the book, Spears said that she would’ve chosen to have the baby, however, “Justin was so sure that he didn’t want to be a father.”

She wrote that undergoing the abortion was “one of the most agonizing” moments of her life.

Britney Spears and Justin Timberlake of *NSYNC at the Shrine Auditorium in Los Angeles.JEFFREY MAYER/WIREIMAGE

In the book, Spears also acknowledged the pair’s mutual infidelity.

“There were a couple of times during our relationship when I knew Justin had cheated on me,” she wrote. “Especially because I was so infatuated and so in love, I let it go, even though the tabloids seemed determined to rub my face in it.”

Spears also addressed her own infidelity with Wade Robson.

“We were out one night and we went to a Spanish bar. We danced and danced. I made out with him that night,” she wrote. “I was loyal to Justin for years, only had eyes for him with that one exception, which I admitted to him.” At the time, they moved past it and stayed together.

Timberlake has yet to address anything Spears wrote in her book, though in 2021 he posted on X, the social media site formerly known as Twitter, in support of Spears’ 13-year conservatorship being ended. It was officially terminated in November 2021.

“We should all be supporting Britney at this time. Regardless of our past, good and bad, and no matter how long ago it was… what’s happening to her is just not right,” he wrote on X at the time. “No woman should ever be restricted from making decisions about her own body. No one should EVER be held against their will… or ever have to ask permission to access everything they’ve worked so hard for.”

June 2024: Timberlake Arrested for DWI in Long Island

During a brief break on his Forget Tomorrow World Tour, Timberlake was arrested on a DWI charge after leaving the American Hotel in Sag Harbor, New York on Tuesday, June 18.

He was charged with one count of driving while intoxicated and two citations, one for running a stop sign and one for failure to keep in lane.

A source told PEOPLE that Timberlake was “hanging out with friends.”

According to his arrest report, which was obtained by PEOPLE, Timberlake told his arresting officer that he “had one martini” and was following his friends home.

The report said that an officer saw the singer’s 2025 BMW run through a stop sign and failed to stay on the right side of the road. It also said that Timberlake’s “eyes were bloodshot and glassy.”

Justin Timberlake leaving court in Sag Harbor on June 18, 2024.MATT AGUDO/INSTAR IMAGES

Per the report, Timberlake was arrested and taken to Sag Harbor Police Headquarters to be processed, when he refused multiple times to take a chemical test.

He was held overnight and arraigned the following morning.

Timberlake is due back in court for a hearing on July 26.

In a statement to PEOPLE on Wednesday, June 19, the musician’s attorney, Edward Burke Jr. said that he “looks forward to vigorously defending” him against the allegations.

Burke Jr. added, “He will have a lot to say at the appropriate time. He is currently awaiting full discovery from the DA’s office.”

Meanwhile, another source told PEOPLE that Timberlake’s wife, Biel, 42, was “not happy” about her husband’s arrest, but will “always be by his side.”