Justin Timberlake's Most Controversial Moments Ever

Justin Timberlake became a hot topic in 2021. Unfortunately for him, the uptick in publicity had nothing to do with the release of his movie, Palmer, or any of the music that he dropped toward the end of 2020. Instead, the spotlight was glaring on his past behavior. For the most part, Timberlake has had a "positive" public persona, somehow managing to skate by and find continued success despite his many scandalous moments. However, these public missteps finally caught up with him.

In February 2021, a Twitter user wrote, "Justin Timberlake needs to publicly apologize to Britney Spears AND Janet Jackson." That person didn't tag Timberlake in her tweet, but the singer-actor later admitted that he saw many "messages, tags, comments, and concerns" that called him out when he posted a written apology on Instagram that same month. Copping to benefitting from "a system that condones misogyny and racism," he confessed that he "can do better" and that he "will do better." The boy band alum wrote, "I specifically want to apologize to Britney Spears and Janet Jackson both individually," acknowledging that he "failed" them. However, he didn't actually address any of the specific ways that he wronged both women. 

So, why did all of this resurface in 2021, and what are people so pressed about? Let's take a look back at some of Justin Timberlake's most controversial moments that he failed to reference in his apology.

During Justin Timberlake and Janet Jackson's 2004 Super Bowl Halftime performance, he pulled at the fabric on her costume, exposing her breast. It was a brief controversy for Timberlake, but in contrast, it drastically changed Jackson's career. Soon after, The New York Times reported that she was supposed to present at the Grammy Awards. However, production sources said she "would either step down herself or be asked to step down." Conversely, JT performed and won two Grammys. During an acceptance speech, he said, "I know it's been a rough week on everybody. What occurred was unintentional, completely regrettable and I apologize if you guys are offended," according to Rolling Stone. However, there was no mention of how "rough" it was for Jackson who wasn't at the ceremony.

In a 2006 interview, Jackson told Oprah Winfrey, "All the emphasis was put on me, not on Justin." She considered him to be her "friend," but they apparently hadn't actually spoken since that night. She then vaguely stated that there are "certain things you just don't do to friends."

When Timberlake was announced as the 2018 halftime show performer, some people were outraged, with one tweeting, "Not to be negative, but why is Justin playing the superbowl and Janet is still blacklisted? @NFL #JusticeForJanet." Meanwhile, The Chi's Lena Waithe wrote on Twitter, "You know what would be dope. if Justin actually brought Janet on stage 30 seconds into his performance and let her finish the halftime show." Unfortunately, Timberlake didn't do that.

In 2018, women wore black outfits at the Golden Globe Awards in support of the Time's Up initiative against sexual misconduct, per Harper's Bazaar. Prior to the show, Justin Timberlake shared an Instagram selfie with his wife, Jessica Biel, writing, "Here we come!! And DAMN, my wife is hot! #TIMESUP #whywewearblack." 

Some social media users felt that caption was tone deaf, with one tweeting, "Doesn't 'DAMN, my wife is hot' play right into the whole reason for the #WhyWeWearBlack campaign?" Someone else tweeted, "You can't say #TIMESUP right after you just did a movie with Woody Allen, knowing everything horrific he has done." Allen's adopted daughter, Dylan Farrow, accused the director of sexual abuse in 2014. Timberlake worked with Allen on the 2017 movie, Wonder Wheel. According to another Twitter user, "you can't work with abusers and condemn them at the same time!!! it doesn't work that way!!!"

Two weeks after Timberlake's Time's Up post, he tweeted, "Can someone please explain the saying, 'You just want your cake and to eat it too.'" That's when Farrow hit back with, "The saying means, for example, you can't support #TIMESUP and praise sexual predators at the same time. You can't retain your credibility as an activist (i.e. – retain the cake) and, at the same time, praise a sexual predator (i.e. – eating the cake)." Despite the pushback from Farrow and some disgruntled tweeters, Timberlake's career persisted, as per usual.

Britney Spears shared her desire to remain a virgin until marriage, which was discussed during The New York Times Presents: Framing Britney Spears documentary in February 2021, in relation to her romance with Justin Timberlake, which lasted from 1998 to 2002. After the split, Timberlake appeared on Hot 97's Star and Buc Wild Morning Show, where he was asked, "Did you f**k Britney Spears?" He confessed with a laugh, "Okay, yeah I did it!" According to GQ, Timberlake also said, "I did it. I'm dirty," when he was asked about the two having oral sex.

Timberlake later discussed that radio interview with Rolling Stone, claiming, "I thought, 'Well, maybe that's the sense of humor here.' But anybody who listened to that show has to know it's a joke." He went on to allege, "They were promising me spins on the radio, so I was just pimping spins. I thought it was funny as hell. That's just my sense of humor." Meanwhile, during a 20/20 interview, Barbara Walters quoted Spears as saying, "Good morals mean waiting to have sex until after you've been married." When Walters asked, "Did you and she live up to this during your relationship?" Timberlake laughed and said "sure" twice. 

Spears later told W magazine (via Entertainment Weekly), "I thought he was the one. But I was wrong! I didn't think he was gonna go on Barbara Walters and sell me out." Unfortunately for Spears, Timberlake had an album to promote.

In 2002, Justin Timberlake released the "Cry Me A River" music video, which featured a Britney Spears look-alike wearing one of the pop princess' beloved newsboy hats. The song and video very strongly implied that Spears cheated, per Genius. 

Spears later told Rolling Stone that Timberlake asked for her blessing to have a doppelgänger in the video... without showing her footage or revealing any context. She recalled, "I hadn't seen it. Then it came out, and I said, 'I should've freakin' said no to this s**t!'" Spears reportedly asked, "Why did you do this," and he responded, "Well, I got a controversial video." Spears said, "He got what he wanted," which she described as "such a desperate attempt" and "a great way to sell the record." During an appearance on MTV's Total Request Live, Timberlake explained, "The video is not about her. The video is about me," per MTV News. 

But that wasn't the only time Timberlake seemingly sang about Spears. During his 2002 Barbara Walters interview, he performed a never-released ballad, where he sang, "Hey girl, at least you gave me another song about a horrible woman," in the middle of a discussion about his split from Spears. In 2006, Timberlake dropped "What Goes Around... Comes Around," which had the lines, "You spend your nights alone / And he never comes home." This was right in the midst of rumors that Spears' then-husband Kevin Federline's "partying" was "the last straw" leading to their divorce, according to People. What a coincidence.

In December 2019, The Sun shared photos and videos of Justin Timberlake in New Orleans with his Palmer co-star, Alisha Wainwright. An eyewitness said, "At one stage he grabbed her hand and rested it on his knee. She then gently started stroking his leg." What's wrong with that? Well, Timberlake has been married to Jessica Biel since 2012. The onlooker claimed that the singer "clutched [Wainwright's] hand with both of his and was playing with her hands," as well. To make matters worse, he wasn't wearing his wedding ring in any of the photos or videos.

Shortly after the photos emerged, Timberlake issued a written apology via Instagram. He told his followers, "I feel it is important to address recent rumors that are hurting the people I love." Describing his behavior as "a strong lapse in judgement," the singer-actor emphasized that "nothing happened between" him and Wainwright. However, Timberlake admitted, "I drank way too much that night and I regret my behavior."

"I apologize to my amazing wife and family for putting them through such an embarrassing situation," Timberlake continued, noting that he was "focused on being the best husband and father." Unbeknownst to the world, Biel was pregnant at the time, and gave birth to the couple's second son eight months after those photos surfaced, per the Daily Mail. Timberlake ended his apology by sharing that he was "excited" for people to see Palmer, which was debatably too much.

In 2013, Justin Timberlake dropped the single "Take Back the Night." The song's title was problematic because Take Back the Night is also the name of an organization that strives to "end sexual assault, domestic violence, dating violence, sexual abuse and all forms of sexual violence," per its official website. The group threatened legal action against Timberlake for using its trademarked name, with Executive Director Katherine Koestner telling Rolling Stone, "It just shows how far we have to go when Take Back the Night as a historic movement to end sexual violence in all forms is still not widely enough known, according to Mr. Timberlake, that he claims he didn't know that we existed." 

In addition to violating trademarks, Koestner took issue with the song's message, remarking, "In reading the lyrics, I think they're open to a lot of interpretation. They're clearly sexual, but they're not about sexual assault — so I think the problem may be just confusion with how an overtly sexual song matches with the mission of ending sexual violence."

Timberlake released an apology statement to Radar, claiming, "I was made aware of an organization of the same name called The Take Back The Night Foundation." Noting that the song and its lyrics don't "have any association with the organization," he concluded, "It is my hope that this coincidence will bring more awareness to this cause." Some felt that this may have also brought more awareness to his ignorance.

According to BET, Justin Timberlake tweeted (and then deleted) in August 2014, "A happiest of Bdays to my mother chucking ninja, @Madonna!! Hope you have a great one, M!" The post sparked immediate backlash for multiple reasons. 

Us Weekly reported that writing "mother chucking ninja" was another way for him to say "mother f**king n***a." Previously, Grantland shared that Katy Perry used the word "ninja" as a substitution for the "N" word when she sang along to Jay-Z and Kanye West's song, "N****s in Paris" during a 2012 Radio 1 performance. In response to Timberlake's post, one Twitter user declared, "I just ended my relationship w/Justin," and another posted, "'Mother chucking ninja.' Get Justin Timberlake the f**k out of here." 

According to the Daily Mail, Timberlake's rep didn't respond to phone calls, and the singer-actor hadn't apologized for the since-deleted social media gaffe. Madonna did not acknowledge it either. Furthermore, the outlet pointed out that the timing for Timberlake's tweet couldn't have been any worse, since it was shortly after the Black Lives Matter protests turned violent in Ferguson, Mo., following the fatal shooting of Michael Brown. In fact, one person tweeted, "Justin Timberlake chose *this* week to call Madonna 'my ninja'? I just can't." 

Instead of saying "sorry," Timberlake retweeted a post, which said, "The world is watching #Ferguson. [And we pray.]," per the Daily Mail. Nevertheless, Timberlake's career didn't face any consequences from this error in judgement.

In 2016, Grey's Anatomy star Jesse Williams received The Humanitarian Award at the BET Awards, per People. During his speech, Williams denounced people for "ghettoizing and demeaning our creations, then stealing them, gentrifying our genius, then trying us on like costumes before discarding our bodies like rinds of strange fruit." He explained that he was upset with everyone who had been "burying Black people out of sight and out of mind while extracting our culture, our dollars, our entertainment like oil."

Apparently, that speech resonated with Justin Timberlake, who tweeted, "@iJesseWilliams tho... #Inspired #BET2016." Many Twitter users took issue with Timberlake, including journalist Ernest Owens, who asked, "So does this mean you're going to stop appropriating our music and culture? And apologize to Janet [Jackson] too. #BETAwards." As reported by People, Timberlake replied (and soon deleted), "Oh, you sweet soul. The more you realize that we are the same, the more we can have a conversation. Bye." In response to Timberlake's remarks, someone tweeted, "by saying we are all the same [you] dismissed Jesse Williams speech entirely and proved his point at the same time well done." 

Following the backlash, the Grammy winner took to Twitter with, "I apologize to anyone that felt I was out of turn. I have nothing but LOVE FOR YOU AND ALL OF US." However, there are lots of people who couldn't look past some of Timberlake's admittedly questionable decisions, including but not limited to getting cornrows...

Justin Timberlake has served up many hair moments throughout his career, from his natural curls, to a buzz cut, and many styles in between. However, only one style truly caused controversy: his decision to sport cornrows as a white male. Timberlake has never actually apologized for rocking this style, which originated within the Black community, but he did sort of address the move during a 2011 interview with Playboy. When asked if he had "any particular fashion regrets," the Timberlake joked (via HuffPost), "God, I feel I've gone to therapy just to erase some of them. The cornrows I wore with 'N Sync. That was pretty bad."

Unfortunately for Timberlake, those mistakes will be on the internet forever, while continuing to upset many people. One person tweeted in 2018, "When, say, Justin Timberlake has cornrows while black folks with cornrows are stigmatized and treated as potential or probable criminals, that's cultural appropriation—Timberlake profits with his 'cool' hairstyle, while the black folks who started doing the style are punished." Another Twitter user said, "What's unfair is the insane amount of money Justin Timberlake made while stealing black art, strolling down red carpets in cornrows & sacrificing Janet Jackson. Boy, bye bye bye."

With so many of Timberlake's past mistakes resurfacing, many eyes are on the singer-actor to see how he behaves post-Instagram apology. We hope Timberlake truly learned some lessons in 2021 — because, if not, he may just find out that "What Goes Around... Comes Around."