Justin Timberlake’s Controversial Moments Amidst His DWI Arrest Case: Britney Spears Alleged Cheating Allegations To Hand-Holding Moment With Alisha Wainwright
Back in November 2002, Timberlake released his solo Cry Me a River, which garnered attention for featuring an unfaithful girlfriend resembling his ex-girlfriend, Britney Spears.
After facing several controversies throughout his life, Justin Timberlake still finds himself entangled in yet another scrutiny as he got arrested on a DWI charge while on Long Island. From his controversial relationship with Britney Spears back when the pop star was in the boy band, NSYNC, to ripping off Janet Jackson’s top at Super Bowl performance, here’s the timeline of Timberlake’s controversies over the years.
April 2002: Timberlake Went Solo
In April 2002, Timberlake abruptly left NSYNC to launch his solo career. While he explained the reason to “follow my heart”, as per The Hollywood Reporter, his former band-mate Joey Fatone revealed that he was “blindsided” by Timberlake’s solo career. Fantone told Yahoo Entertainment, “I was not blindsided by [NSYNC’s breakup]. 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. It was more of, ‘Hey, I’m going to do some music, and then we’ll get back together.’ That’s what that was.”
November 2002: Timberlake’s Cry Me a River Pointing Britney Spears Cheating Allegations
Back in November 2002, Justin Timberlake released his solo Cry Me a River, which garnered attention for featuring an unfaithful girlfriend resembling his ex-girlfriend, Britney Spears. His song was the second single from his debut solo album, Justified. Reflecting on the song, Timberlake told People that he wouldn’t explicitly say who his songs were about, but they would “bring clarity. They’re explanatory. I don’t have to say it.”
In a 2003 interview with Diana Sawyer, Spears was asked, “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?” She replied, “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? 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.”
February 2004: Timberlake Rips Janet Jackson’s Top At Super Bowl
During the Super Bowl’s halftime show in 2004, Justin Timberlake, who was the surprise guest, ended up becoming a scandal when he ripped off Jackson’s top, revealing her bare breasts on live TV. The moment became “Nipplegate.” Following the incident, the SexyBack singer shared an apology stating, “it was not intentional and is regrettable.” After the Nipplegate, Jackson’s music was blacklisted by radio and television stations.
Again in 2004, he opened up about the incident during an interview adding that he was “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.” He also revealed that he and Jackson had resolved things and wrote a lengthy Instagram post to Jackson, stating his apology after the release of the Framing Britney Spears documentary in 2021. Later in 2022, Jackson also addressed the incident and clarified that “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, Justin Timberlake allegedly cheated on his then-girlfriend Jessica Biel with Olivia Munn. However, a source revealed to People that “there was never any proof” of infidelity.
November 2019: Hand-Holding Controversy With Alisha Wainwright
In 2019 when Timberlake was filming his movie Palmer in New Orleans, he was spotted holding hands with co-star Alisha Wainwright as per The Sun. In the videos and photos discovered by the outlet, the singer was enjoying drinks with the group and the actress appeared to rest her hand on his knee. In images, the pair was also seen holding hands. However, the inside source revealed that it was “completely innocent.”
Timberlake also addressed the situation on his Instagram and apologized to his wife Biel. He stated “I feel it is important to address recent rumors that are hurting the people I love.” He further gave an apology to his wife adding, “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 Address Her Past With Timberlake In Her Memoir
In her 2023 memoir, The Woman in Me, Britney Spears addressed her relationship with Justin Timberlake revealing that she got pregnant with his baby but had a medical abortion at their home. She wrote that the pregnancy “was a surprise” but not “a tragedy”. She added, “But 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.”
She also explained that she was ready to have the baby but “Justin was so sure that he didn’t want to be a father.” Spears described getting an abortion as “one of the most agonizing” moments of her life. Additionally, Spears addressed the pair’s mutual infidelity, describing that she knew “he had cheated on me,” but she “let it go”.
June 2024: Timberlake Arrest on DWI Charge
Recently, the What Goes Around Comes Around singer was arrested in Long Island on a DWI charge after leaving the American Hotel in Sag Harbor. He was reportedly on a short break on his Forget Tomorrow World Tour. He was charged with one count of driving while intoxicated, one for running a stop sign, and one for failure to keep in lane. However, he revealed that he only “had one martini” and was held overnight where he refused to take a chemical test. Following the next day, he was released but is due back in court for a hearing on July 26.
