Controversial Justin Timberlake Moments We Can't Forget About

Justin Timberlake's life has been plagued with controversy ever since he first rose to stardom. After enjoying the spotlight in the iconic boy group NSYNC for several years, Timberlake departed the band to pursue a solo career in 2002. During a 2017 chat with The Hollywood Reporter, the "My Love" singer offered some insight into his decision. "I was growing out of it," he admitted. "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." 

However, it doesn't seem like his bandmates were aware of Timberlake's feelings at the time. While speaking to Yahoo! Entertainment in 2023, Joey Fatone confessed that he was completely thrown by "The Social Network" star's decision to go solo as opposed to the band's split more generally. Fatone also pointed out that Timberlake had given his bandmates the impression that he would pursue his solo career for a bit before making his triumphant return to the band. 

Unfortunately, Fatone and the others only realized a while later that Timberlake was likely telling them what their record label had instructed him to. While fans were equally blindsided by Timberlake's sudden departure from the band, he gave them plenty to love, from his new music to his iconic romance with Britney Spears. On the outside, the beloved couple seemed to have the perfect relationship, but we only learned the truth about their union after they broke up.

Shortly after Britney Spears and Justin Timberlake went their separate ways, he dropped "Cry Me A River," a scathing track where he essentially accused an unnamed ex of cheating on him. Of course, people speculated that the song was about Spears, and Timberlake all but confirmed the rumors by having a Spears lookalike appear in the accompanying music video. In 2003, the "Womanizer" hitmaker shared with Rolling Stone how her ex calmly informed her that the video would portray her in a negative light before its release. Unfortunately, Spears only realized that he had downplayed things when she watched the video with the rest of the world, and she was left wishing that she had done something to stop its release. 

Although the "Mirrors" singer heavily implied that "Cry Me A River" was about Spears, he still remained coy about the reason for their breakup in interviews. When Barbara Walters asked Timberlake if the "Circus" songstress was unfaithful, he essentially evaded the question with a non-answer. Instead, the former boybander told a sweet story about how he and his ex promised to keep the reason for their split private. 

However, Timberlake's statements felt a bit disingenuous when he went on to play an unreleased song called "Horrible Woman." In it, Timberlake sang that his former flame wasn't "worth the gas in my BMW" and "At least you gave me another song about a horrible woman." Once again, he somewhat unconvincingly maintained that it wasn't about Spears.

Britney Spears' bestselling 2023 memoir "The Woman In Me" revealed some of the most tragic details of her relationship with Justin Timberlake. While the iconic pop star acknowledged cheating on Timberlake with Wade Robson, Spears claimed that her beau had also been unfaithful on more than one occasion. Further, the "Baby One More Time" hitmaker disclosed that she got pregnant during their relationship. The bestselling author wrote that the pregnancy was "a surprise, but for me, it wasn't a tragedy," per People. 

Unfortunately, the "SexyBack" singer didn't share the same sentiment because he believed they weren't mature enough for the responsibilities that parenthood brought. So, Spears ended up getting an abortion, even though she was totally against the idea. "To this day, it's one of the most agonizing things I have ever experienced in my life," the legendary star sadly conceded. In Timberlake's chat with Barbara Walters, he painted a sweet picture of their split, where both parties mutually agreed to have each other's backs afterward. 

However, Spears remembered things differently in her memoir, writing that the "Rock Your Body" singer ended their 3-year relationship with a text. If that wasn't bad enough already, he chose to send the message when she was busy filming the music video for Darkchild's remix of "Overprotected." And Spears naturally wasn't pleased with Timberlake using their breakup to his advantage, as she noted, "The thought of my betraying him gave the album more angst, gave it a purpose: s*** talking an unfaithful woman," per Cosmopolitan.

Janet Jackson was at the peak of her career when she performed at the Super Bowl with Justin Timberlake. However, the once-in-a-lifetime opportunity was tainted when he ripped off a part of Jackson's costume to reveal her breast and a nipple accessory. In the 2021 documentary, "Malfunction: The Dressing Down of Janet Jackson," the halftime show's director, Beth McCarthy-Miller, revealed that the "All For You" hitmaker was tearing up backstage. However, Timberlake didn't seem too bothered by what went down, as he bragged to "Access Hollywood" shortly afterwards that he "loves giving y'all something to talk about," per Billboard. 

The following day, Jackson publicly apologized for the mishap in a statement, but Timberlake remained silent. While the "Together Again" songstress bore the brunt of the public criticism for the incident, her co-star still felt victimized. Speaking on KCBS, the "Selfish" singer claimed that his fellow performer and her choreographer had instructed him to tear her top at the end of their performance, complaining, "I'm frustrated at the whole situation."

Timberlake continued, "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," per The Washington Post. In fact, the singer ultimately only apologized during his 2004 Grammys acceptance speech a few days later, while Jackson had to skip out on the big night altogether. Despite everything, Jackson and Timberlake seemingly remained cordial.

About two years into Justin Timberlake's relationship with Jessica Biel, Us Weekly reported that he had been unfaithful to her. A source revealed to the publication that the Grammy winner had been vying for actor Olivia Munn's affection ever since they met. However, the "X-Men: Apocalypse" star consistently made it clear that she was not interested in being the other woman in his relationship with Biel, so Timberlake supposedly fooled Munn into thinking that it was all over. According to the insider, the pair enjoyed a 3-day fling, during which he also lied to other people by claiming to have ended things with Biel. 

A spokesperson for the singer wrote off the report as completely false. However, Timberlake once again found himself at the center of infidelity allegations in 2019, when The Sun posted a clip of him seemingly holding hands with his "Palmer" co-star, Alisha Wainwright. As the cheating speculation began anew, a source argued to People that the video showed a "completely innocent" chat between friends and further stressed that Timberlake and Wainwright were hanging out in a group setting. 

A few days later, the "In Time" star took to Instagram to set the record straight, clarifying, "A few weeks ago I displayed a strong lapse in judgment — but let me be clear — nothing happened between me and my co-star," per People. He continued, "I drank way too much that night and I regret my behavior. I should have known better." Timberlake apologized to Biel for one of the many times he was accused of cheating. 

In June 2024, Justin Timberlake was arrested for Driving While Intoxicated (DWI) in Sag Harbor, New York. As CNN reported at the time, the former boybander caught the police's eye when he reportedly drove past a stop sign without pausing and couldn't stay in his lane either. After being pulled over, Timberlake promised the officers that he'd only had one drink. However, the Grammy winner supposedly fared poorly on his field sobriety tests, was slurring, and seemed pretty out of it to law enforcement. In fact, Page Six reported that the officer who pulled the NSYNC alum over "was so young that he didn't even know" that he was dealing with a celebrity. A source also recalled a rather awkward encounter between them, infamously declaring, "Justin said under his breath, 'This is going to ruin the tour.' The cop replied, 'What tour?' Justin said, 'The world tour.'" 

In September, Timberlake accepted a plea deal for his high-profile arrest and pleaded guilty to the less serious charge of Driving While Ability Impaired (DWAI). The New York Times confirmed that the deal brought with it a $500 fine, 25 hours of community service, and a public safety announcement. The pop star completed the last part of the plea deal shortly after as he owned up to reporters that his actions on that fateful night were irresponsible, explaining, "I try to hold myself to a very high standard, for myself, and this was not that." Timberlake also strongly urged people in similar positions to never get behind the wheel.