10 times Justin Timberlake exhibited problematic behavior: From DWI arrest to Super Bowl 'Nipplegate'

10 times Justin Timberlake escaped criticism despite being problematic

Justin Timberlake has been at the center of multiple scandals throughout his illustrious career, which began when he was a child. The release of Britney Spears' 2023 memoir brought renewed attention to Timberlake's stormy teenage romance with her. Most recently, Timberlake was taken into custody for a DWI in the Hamptons on June 18 but was later released without bail, according to People. Timberlake faces a single DWI charge along with two tickets for failing to stay in his lane and running a stop sign. Here are the 10 biggest conflicts over the years that Timberlake has managed to escape.

1. Justin Timberlake and Janet Jackson's 2004 Super Bowl 'Nipplegate'

The 2004 Super Bowl incident involving Timberlake and Jackson went viral and was dubbed "Nipplegate." Timberlake unintentionally ripped Jackson's leather top, revealing her breast to 140 million viewers. Later, Timberlake stated that the "wardrobe malfunction" was "not intentional and is regrettable." While Timberlake avoided major consequences from the controversy, Jackson's career and reputation suffered. Since Nipplegate, Jackson has not been invited to participate in a Super Bowl halftime show.

2. Justin apologizes for Super Bowl incident to attend 2004 Grammys

In 2004, Justin Timberlake wasn't simply being courteous when he apologized for his Super Bowl performance during his Grammy acceptance speech. CBS stated that the apology was a condition for his appearance on the show. Consequently, Janet Jackson, his counterpart in the incident, did not attend the Grammys. She was offered the opportunity to present if she also apologized, but she declined, according to Entertainment Weekly.

3. Justin Timberlake's whirlwind romance with Britney Spears

Former 'All New Mickey Mouse Club' stars Timberlake and Spears dated from 1999 to 2002. Years later, Spears revealed in her October 2023 memoir 'The Woman in Me' that Timberlake had cheated on her. She also disclosed that she had an abortion while they were together because she believed Timberlake wasn't ready to be a father. Following the release of her memoir, Spears apologized to Timberlake. In response, Timberlake, now a father of two, stated during a show in NYC that he had no intentions to apologize to "absolutely f**king nobody."

4. Justin Timberlake clapped back to Britney Spears' charges with 'Cry Me a River' performance

Justin Timberlake issued a warning during his performance at the Fontainebleau in Las Vegas in December 2023 before singing 'Cry Me a River,' a song widely believed to be about his ex-girlfriend Britney Spears. According to a TikTok fan video, the singer prefaced the song by saying, "No disrespect." The song's music video caused controversy as it featured a woman portrayed as adulterous, bearing a striking resemblance to the 'Toxic' singer. In 'Cry Me a River,' Timberlake sings the lyrics, "You don’t have to say, what you did / I already know, I found out from him."

5. When Justin Timberlake was spotted canoodling with co-star Alisha Wainwright

In November 2019, seven years into his marriage to Jessica Biel, Timberlake was photographed holding hands with 'Palmer' co-star Alisha Wainwright in New Orleans. According to sources cited by The Sun, Timberlake "appeared to have been drinking heavily and was unsteady on his feet," and he had reportedly taken off his wedding band. In a since-deleted Instagram post, Timberlake later expressed regret for the incident, stating, "I drank way too much that night and I regret my behavior."

6. Cheating allegations with Olivia Munn

In October 2010, Us Weekly reported that Timberlake had an affair with Olivia Munn while he was dating Biel. According to an insider, Timberlake and Munn had a three-day affair after meeting at a MySpace event. At the time, Timberlake's representative denied the accusations, while Munn's representative chose not to comment on them.

7. Justin Timberlake's hit 'Take Back the Night' shares name with popular anti-rape group

Justin Timberlake's 2013 single 'Take Back the Night' shares its name with the popular sexual assault awareness foundation. However, according to TIME Magazine, the song title was not intended to reference or align with the Take Back the Night movement or its registered trademark. Timberlake promptly addressed the issue, expressing sincere regret to the group. He explained that he was unaware of TBTN and its purpose when writing the song and hoped that it would aid in raising awareness of the foundation's work.

8. Justin Timberlake allegedly called out Prince in the lyrics of 'Give It to Me'

Timberlake's hit 'Give It to Me' includes lyrics that allegedly reference American singer Prince, with lines such as, "We missed you on the charts last week, damn, that's right, you wasn't there / Now if sexy never left, then why is everybody on my s**t? / Don't hate on me just because you didn't come up with it..." Reports indicate that Prince responded to Timberlake's release of 'SexyBack' by stating, "For whoever is claiming that they are bringing sexy 'back,' sexy never left!"

9. Justin Timberlake left *NSYNC to pursue a solo career

Timberlake was a founding member of *NSYNC, along with Lance Bass, Joey Fatone, Chris Kirkpatrick, and JC Chasez. Timberlake's desire to pursue a solo career played a significant role in the group's dissolution. In a 2017 interview with The Hollywood Reporter, Timberlake explained, "We were on a stadium tour, and I just felt like the whole thing was too big. It started as a fun snowball fight that was becoming an avalanche. And, also, I was growing out of it."

10. Justin kissed Jessica Simpson to win a wager with Ryan Gosling

Jessica Simpson revealed during a 2020 guest appearance on 'Jimmy Kimmel Live' that she had a (short) romantic relationship with Timberlake following her 2006 divorce from Nick Lachey. She apparently quickly learned that her brief romance with Timberlake was influenced by a wager he placed with Ryan Gosling, his former castmate from 'Mickey Mouse Club.' Simpson said at the time, "Apparently, him and Ryan Gosling had a bet on who would kiss me first when they were 12 years old."