From Pregnancy Scandals to Cheating Allegations, Justin Timberlake’s Greatest Controversies

Top Ten Controversies Faced by Justin Timberlake

Justin Timberlake has faced various challenges throughout his showbiz career. Originating from Star Search and The All New Mickey Mouse Club, Timberlake co-founded 'NSync with fellow MMC cast members JC Chasez, Lance Bass, Joey Fatone, and Chris Kirkpatrick. During the group's pinnacle, Timberlake's role as the lead singer gained further attention due to his romance with Britney Spears. However, Spears' memoir reveals a different narrative, alleging that their relationship from 1999 to 2002 was far from the idyllic romance portrayed to the public. In the aftermath of Spears' revelations, other controversies and scandals from Timberlake's career have resurfaced, prompting reflection on his 2006 hit single What Goes Around...Comes Back Around. However, it's crucial to acknowledge that this latest episode isn't the initial instance where Timberlake has grappled with scandals that tested his public image. Here, we explore ten notable controversies that have marked various points in Timberlake's career.

1. Justin Timberlake's Shocking PDA With Palmer Co-Star, Alisha Wainwright

During the filming of Palmer in New Orleans, a notable incident occurred in December 2019 when Justin Timberlake was photographed holding hands with his co-star Alisha Wainwright at a bar. Following the public attention, a source clarified to Us that the co-stars were simply "just friends," and there was "nothing inappropriate" that took place. Justin Timberlake then issued a public statement. “A few weeks ago, I displayed a strong lapse of judgment — but let me be clear — nothing happened between me and my co-star. 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 via Instagram. 

2. Justin Timberlake's Contribution to The New NSYNC Song

As fans eagerly anticipate a rumored NSYNC album set for release in 2025, they've been treated to a preview of the group's latest song, Better Place per NY Post. This track, created for the upcoming film Trolls Band Together, was officially released online in September 2023. Despite the excitement surrounding the first song from NSYNC in over two decades, some sharp-eared listeners noticed a detail that raised eyebrows – Justin Timberlake is credited separately from the rest of the band on the single. Platforms listing the performers on the track, which is featured on the Trolls Band Together movie soundtrack, present them as “NSYNC and Timberlake,” even though NSYNC comprises Justin Timberlake, JC Chasez, Lance Bass, Joey Fatone, and Chris Kirkpatrick. This separate crediting prompted swift criticism from fans directed at Timberlake.

3. The Bombshell Reason Why Justin Timberlake Left NSYNC

In April 2002, NSYNC disbanded as Justin Timberlake expressed his desire to pursue a solo career. Timberlake elaborated on his departure from NSYNC in a February 2017 profile with The Hollywood Reporter, citing personal growth as the primary reason for his decision. Although Justin Timberlake's departure from NSYNC was surprising to some of his fellow band members, notably Joey Fatone, who perceived it more as a temporary break than a permanent separation, Timberlake had unequivocally communicated his intention to pursue solo opportunities and move on from the group. Fatone expressed in a statement to Variety that he was not blindsided by NSYNC's breakup. “I was growing out of it. 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,” Timberlake explained to The Hollywood Reporter in 2017.

4. Justin Timberlake's Cheating Controversy

Persistent rumors of infidelity have occasionally surrounded Justin Timberlake, with speculations suggesting that he may have been unfaithful to his now-wife, Jessica Biel. One notable instance involved rumors of Timberlake allegedly cheating on Biel with actress Olivia Munn. According to Us Weekly, the Mirrors singer was rumored to have pursued Munn ardently after connecting with her and exchanging numbers at a MySpace event in 2010. Despite these challenges, Timberlake and Biel managed to overcome the adversity and ultimately got married in 2012.

5. Justin Timberlake’s Trouble Over Cultural Appropriation

During the 2016 BET Awards, Jesse Williams, in his acceptance speech for a Humanitarian Award, focused on exposing issues of racism and cultural appropriation within the media and entertainment sector. However, when Justin Timberlake tweeted his admiration for Williams, stating, "@iJesseWilliams tho… #Inspired," the response was not universally positive. In response to the criticism, Timberlake referred to his critic, Owens, as a "sweet soul" and urged for understanding by tweeting, “The more you realize we’re all the same, the more we can have a conversation. Bye.”

6. Justin Timberlake's Contentious Super Bowl Halftime Performance with Janet Jackson

A notable controversy in Justin Timberlake's career unfolded during the 2004 Super Bowl Halftime Show, where he was featured in a performance of Rock Your Body alongside Janet Jackson. The controversy unfolded in the final moments of the performance when Timberlake unexpectedly ripped off a part of Jackson's top, revealing her breasts on live television. This incident, famously dubbed "NippleGate" by the press, quickly became the most searched event in internet history. Jackson faced consequences like the cancellation of her appearance at the Grammy Awards that year. In contrast, Timberlake not only performed at the awards show but also secured two wins. While he did apologize for the incident during his speech, the absence of any reference to his stage partner raised concerns about the disparities in how their careers were affected by the controversy.

7. When Justin Timberlake Characterized Britney Spears as a Harlot

Fans were taken aback by Britney Spears' revelation regarding Justin Timberlake's alleged infidelity. This revelation carried additional weight due to the context of Timberlake hinting at Spears' supposed betrayal in his 2002 breakup track Cry Me a River per People. The accompanying music video even featured a lookalike of Spears as his unfaithful ex. In a 2003 interview with Rolling Stone, Spears disclosed that Timberlake had warned her about the release of the Cry Me a River video, but she never anticipated that he would follow through. Reflecting on the video's plot in her later years, Spears, now 41, described it as portraying "a woman who looks like me cheats on him, and he wanders around sad in the rain." In her memoir, The Woman in Me, Spears delves into the media backlash that depicted her as a "harlot who'd broken the heart of America's golden boy." She clarified that during the time portrayed in the video, she was "comatose in Louisiana," while Timberlake was freely navigating Hollywood. Spears expressed frustration that Timberlake's album and the surrounding media coverage omitted any acknowledgment of his infidelities.

8. Justin Timberlake Allegedly Cheated on Britney Spears

In her memoir, The Woman in Me, Britney Spears, aged 41, openly acknowledges that during their relationship in the early 2000s, she was aware of Justin Timberlake's, now 42, infidelity. Despite knowing Timberlake's unfaithfulness, the Toxic singer chose to remain silent about it at the time, explaining that her deep feelings for him made her hesitant to address the issue. “There were a couple of times during our relationship when I knew Justin had cheated on me. 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 writes. “When *NSYNC went to London in 2000, photographers caught him with one of the girls from All Saints in a car. But I never said anything. At the time we’d only been together for a year.”

9. Justin Timberlake and Britney Spears’ Abortion Scandal

In a significant revelation from Britney Spears' memoir, she opened up about undergoing a medical abortion after becoming pregnant during her relationship with Justin Timberlake. "It was important that no one find out about the pregnancy or the abortion, which meant doing everything at home," Spears, now 41, wrote. "We didn't even tell my family. The only person who knew besides Justin and me was Felicia [Culotta, Spears' former assistant], who was always on hand to help me. I was told, 'It might hurt a little bit, but you'll be fine.'" She writes of the experience, "On the appointed day, with only Felicia and Justin there, I took the little pills. Soon I started having excruciating cramps. I went into the bathroom and stayed there for hours, lying on the floor, sobbing and screaming," as reported by People.

10. Justin Timberlake's Bizarre Encounter with Ginuwine

In Britney Spears' memoir, The Woman in Me, a revealing anecdote from her time with Justin Timberlake sheds light on the former NSYNC member's controversial standing within the Black community. In the audiobook version narrated by actress Michelle Williams, Britney recounts a moment where Justin displayed notable excitement upon encountering R&B singer Ginuwine per HuffPost. Williams reads, “Walking our way was a guy with a huge blinged-out medallion. He was flanked by two giant security guards. J got all excited and said so loud, ‘Oh yeah, fo shizz fo shizz Ginuwine! What’s up homie?’ After Ginuwine walked away, Felicia did an impression of J, ‘Oh yeah, fo shizz, fo shizz. Ginuwine!’ J wasn’t even embarrassed. He just took it and looked at her like, ‘F–k you.’”