Justin Timberlake may be crowned the “King of Pop”, but his kingdom is being shaken amidst the release of Britney Spears’ new memoir The Woman in Me. In the memoir, Spears’ alleges that her relationship with Timberlake, which lasted from 1999 to 2002, was far from the picture-perfect romance that fans envisioned it was back then. In the wake of the Britney Spears’ allegations, comes the resurrection of other Justin Timberlake controversies and scandals throughout his career.

All this drama has got us thinking about Justin Timberlake’s 2006 smash single “What Goes Around…Comes Back Around”, as it seems his past is coming back to haunt him from the pages of Spears’ book. But fans might remember, this isn’t the first time Timberlake has found himself entangled in controversies that compromise his reputation.

Colin Farrell and Justin Timberlake have reportedly threatened to sue Britney Spears as she spills “passionate” affair with Farrell in her memoir.

10Justin Timberlake’s Credit On The New NSYNC Song

Justin Timberlake Is Credited Separately On NSYNC’s 2023 Song ‘Better Place’

Year : 2023

While fans await a rumored NSYNC album in 2025, they can quell their excitement with NSYNC’s brand-new song, “Better Place.” The boy band’s song officially dropped online in September 2023, made for the upcoming flick, Trolls Band Together. As fans came down from first track heard from the group in over 20 years, some eagle-eyed listeners noticed something that doesn’t quite sit right with them: Justin Timberlake is credited separately from the rest of the band on the single.

Performers on the track, which is included on the upcoming Trolls Band Together movie soundtrack, are listed as “NSYNC and Timberlake” on some platforms — even though NSYNC consists of Justin Timberlake, JC Chasez, Lance Bass, and Joey Fatone, and Chris Kirkpatrick. Fans were quick to slam Justin Timberlake over the crediting.

“NSYNC ft. Justin Timberlake!?? I think the f–k not,” one fan wrote Friday on X, the platform previously known as Twitter.

“I’ve loved Nsync since childhood, and Justin was always my guy, but seeing the song say “N*Sync & Justin Timberlake” is like wtf?” another added. “Imagine ‘Destineys Child & Beyoncé.’ Sorry dude that is such a bad look.”

Per TMZ, the reason Justin Timberlake was credited on the new NSYNC song separately is strictly for algorithm purposes. We’re told because Justin’s the only one who has released hits in the era of streaming, it was decided to put his name next to the group.

RELATED

Justin Timberlake Was Caught Making A Huge Confession When NSYNC Played ‘Never Have I Ever’ On The Ellen Show

Ellen DeGeneres seemed to take it upon herself to make a surprising revelation about one of the NSYNC members.

9Justin Timberlake’s Controversial PDA With Palmer Co-Star Alisha Wainwright

Justin Timberlake Spotted Holding Hands With Alisha Wainwright Off Set

Via AppleTV

While filming Palmer in New Orleans, Justin Timberlake was spotted holding hands with his co-star Alisha Wainwright at a bar in December 2019. The photos also showed Wainwright placing her hand on Timberlake’s knee. A source subsequently told Us that the co-stars were “just friends” and “nothing inappropriate” occurred.

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,” he wrote via Instagram. “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].”

8The Scandalous Reason Justin Timberlake Left NSYNC

Years After His Exit, Justin Timberlake Revealed He Left NSYNC Because He Outgrew The Boy Band

Via: TheThings

Year : 2017

NSYNC disbanded in April 2002, as Justin Timberlake wanted to go solo.

“I was growing out of it,” Timberlake explained as the reason he left NSYNC to The Hollywood Reporterin a February 2017 profile. “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.”

He continued, “We were on a stadium tour, and I just felt like the whole thing was too big. It started out as a fun snowball fight that was becoming an avalanche.”

Justin Timberlake’s NSYNC exit was shocking to some of his band members, specifically Joey Fatone who didn’t see his exit as permanent, but more of a temporary hiatus. “I was not blindsided by [NSYNC’s breakup],” Fatone said to Variety. “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.”

Fatone also said it was Justin Timberlake’s permanent departure that allowed him to follow his own path to his respective success. “We thought he was just going to go out and just come back after the [‘Justified’] tour,” he continued. “I was like, ‘OK.’ But then when he went on tour and then things started going, I was like, ‘All right, I’ll go do Broadway.’ That’s when I did Broadway. I started doing ‘Dancing With the Stars.’ I started hosting TV shows and doing my own thing, and that was what led me.”

7Justin Timberlake’s Controversy Over Cultural Appropriation

Justin Timberlake’s Support Of Jesse Williams’ Speech Took A Wrong Turn

Via YouTube

Year : 2016

While accepting a Humanitarian Award at the 2016 BET Awards, social justice activist and former star of Grey’s Anatomy, Jesse Williams delivered a speech that highlighted racism and cultural appropriation in media and entertainment. In the speech, Williams spoke about how “the invention of whiteness uses and abuses” Black people. “Ghettoizing and demeaning our creations then stealing them, gentrifying our genius and then trying us on like costumes before discarding our bodies like rinds of strange fruit.”

While millions of people shared and applauded Jesse Williams’ speech on Twitter, Justin Timberlake joined in. The former NSYNC member tweeted his praise writing, “@iJesseWilliams tho… #Inspired”.

Timberlake’s tweet was not well received by all, notably many who claimed that Justin Timberlake had been appropriating Black culture for years in his music and his public persona. Following his tweet, writer Ernest Owens called Justin Timberlake out writing, “So does this mean you’re going to stop appropriating our music and culture? And apologize to Janet too.”

Timberlake responded by calling Owens, a “sweet soul” and tweeted back, “The more you realize we’re all the same, the more we can have a conversation. Bye.”

His words were not received well and was considered a “tone-deaf” response and, after facing more backlash, he deleted the tweet and fired off a few clarifications, saying he “responded to a specific tweet that wasn’t meant to be a general response” and that “we are all one…one human race.”

Fans were not pleased with Justin Timberlake’s apology towards Britney Spears, but it seems like the pop icon isn’t as bothered.

6Justin Timberlake’s Cheating Controversy

Justin Timberlake Allegedly Cheated On Jessica Biel With Olivia Munn During A Three-Day Fling

Instar

Year : 2010

Those pesky infidelity rumors are never too far from Justin Timberlake who was speculated to have been unfaithful to now-wife, Jessica Biel. In one instance, Timberlake was rumored to have allegedly cheated on Biel with actress Olivia Munn. Per Us Weekly, the “Mirrors” singer was said to have pursued Munn relentlessly after the pair connected and exchanged numbers following a MySpace event in 2010.

Olivia Munn allegedly resisted Justin Timberlake under the notion that he was still with Jessica Beil back then but, when he had convinced her otherwise, she took him to her hotel, the Gansevoort Park Avenue NYC, Sept. 27 and 28, where “they were openly affectionate,” per Us Weekly.

Timberlake and Biel were eventually able to overcome the adversity and ended up getting married in 2012. They later welcomed sons, Silas and Phineas.

5Justin Timberlake’s Controversial Super Bowl Halftime Show With Janet Jackson

Justin Timberlake’s Halftime Show Performance Had An Unexpected Reveal That Humiliated Janet Jackson.

TheThings

Year: 2004

Perhaps one of the most notable Justin Timberlake controversy of his career was the “revealing” Super Bowl Halftime Show with Janet Jackson of 2004. To close off the show, the two performed “Rock Your Body.” All was well until the very last second when Justin Timberlake ripped off a part of Janet Jackson’s top and revealed her breast on live television. The incident, dubbed “NippleGate” by the press, became the most searched event in internet history.

At the time when the onstage wardrobe malfunction transpired, it was Jackson’s career that had suffered over Timberlake’s. Not only was she subjected to countless interviews and repeatedly asked whether she had “planned” the reveal, but she was also blacklisted from major TV channels and radio stations.

Janet Jackson’s Grammy Awards appearance was also canceled that year. Meanwhile, Justin Timberlake was not only allowed to perform at the awards show, but he also won two awards. He did take the opportunity to apologize for the incident in his speech but made no mention of his stage partner.

It would be 17 years later, in 2021, that Justin Timberlake would finally address the matter directly, in which he apologized to Janet Jackson and Britney Spears. In an Instagram post, the former NSYNC member wrote ,“I’ve seen the messages, tags, comments, and concerns and I want to respond. I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn, or did not speak up for what was right.” Timberlake continued, saying he understands that he “fell short in these moments and in many others and benefited from a system that condones misogyny and racism.”

“I specifically want to apologize to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed.” Finally, Timberlake said he felt “compelled to respond, in part, because everyone involved deserves better.” He then called it “a larger conversation” that he “wholeheartedly” wants to be part of and grow from.

4Justin Timberlake Paints Britney Spears As A Harlot

Justin Timberlake Reveals Britney Spears Cheated With ‘Cry Me A River’ Video, Tarnishing Her Reputation

via: Instar

Year: 2002

Fans were shocked by Britney Spears‘ revelation about Justin Timberlake’s alleged infidelity especially because—in 2002— he hinted that Britney Spears had cheated on him with the breakup track “Cry Me a River,” in which he cast a lookalike of the singer as his cheating ex in a music video. In a 2003 interview with Rolling Stone, Spears revealed that Timberlake warned her that he would be releasing the “Cry Me a River” video, but it was “the last thing” she thought he would do.

Britney Spears, 41, reflects in The Woman in Me on the 2002 video, the plot for which she describes as, “a woman who looks like me cheats on him and he wanders around sad in the rain.” The “Hold Me Closer” singer says the media backlash from the clip painted her as a “harlot who’d broken the heart of America’s golden boy,” when in actuality, she was “comatose in Louisiana, and he was happily running around Hollywood.”

“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 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,” Spears wrote.

Back then, the tabloids had attacked Britney Spears over the allegations and Justin Timberlake fueled the flames with an interview four years later that criticized the “Stronger” singer.

“When we initially parted ways I felt like she had a couple of opportunities to just sort of stick up for me, and she didn’t. Which is fine. But at that time, you know, I fought back,” he told GQ in 2006. “I used my mind. I came up with a song.”

In her memoir, Britney Spears confirmed the long-running rumor that she cheated on Justin and confessed that she once kissed dancer Wade Robson during a night out. She claimed she told the NSYNC singer about her transgression, and they moved on from it.

3Justin Timberlake Cheats On Britney Spears, Allegedly

In Her Memoir, Britney Spears Reveals Justin Timberlake Cheated On Her During Their Relationship

via Instar

Year: Early 2000s

In her memoir The Woman in Me, Britney Spears, 41, revealed that she knew Justin Timberlake, now 42, had not been faithful to her while they were in a relationship in the early 2000s. The “Toxic” singer shared that, while she knew Timberlake was cheating, she refrained from saying anything because she was absolutely head over heels for him.

“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.”

Spears also opens up about another time Justin Timberlake strayed when the pair were in Las Vegas.

“Another time, we were in Vegas, and one of my dancers who’d been hanging out with him told me he’d gestured toward a girl and said, ‘Yeah, man, I hit that last night,’” she writes. “I don’t want to say who he was talking about because she’s actually very popular, and she’s married with kids now. I don’t want her to feel bad.”

The pop star says her friend was “shocked” by his words, and “believed Justin was only saying it because he was high and felt like bragging.”

“There were rumors about him with various dancers and groupies,” she writes. “I let it all go, but clearly, he’d slept around. It was one of those things where you know but you just don’t say anything.”

2Britney Spears’ Pregnancy Scandal

Britney Spears Revealed That She Was Once Pregnant With Justin Timberlake’s Baby

Year: Early 2000s

Britney Spears’ memoir dropped another major bombshell when she shared details about the medical abortion she had after she became pregnant with Justin Timberlake’s baby when they were dating.

“It was important that no one find out about the pregnancy or the abortion, which meant doing everything at home,” Spears, now 41, writes. “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.”

At the time, Britney Spears recalls, Justin Timberlake, now 42, tried to comfort her. “Justin came into the bathroom and lay on the floor with me,” she writes. “At some point he thought maybe music would help, so he got his guitar and he lay there with me strumming it.”

What’s more is that Spears’ revealed she had an abortion because Timberlake didn’t want to be a father, and that— had it been up to her, she would have had the child.

“It [the pregnancy] was a surprise, but for me, it wasn’t a tragedy. I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I’d anticipated,” Spears, now 41, writes of the pregnancy in the book. “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.”

“If it had been left up to me alone, I never would have done it. And yet Justin was so sure that he didn’t want to be a father.”

Spears writes of her experience undergoing the abortion, “To this day, it’s one of the most agonizing things I have ever experienced in my life.”

Fans have since speculated that Britney Spears hinted at her alleged pregnancy with her hit single “Everytime.” The song’s lyrics, especially in the chorus, where Spears sings about feeling small without her partner and needing him, have sparked discussions about its connection to her experience.

1Justin Timberlake’s Controversial Interaction With Ginuwine

Britney Spears Recalled Justin Timberlake Using A ‘Blaccent’ When He Ran InTo Singer Ginuwine

Year: Early 2000s

Britney Spears’ memoir, The Woman in Me, exposed another shocking anecdote from her relationship with Justin Timberlake— and it has the former NSYNC member’s polarizing reputation with the Black Community taking another hit. In her book, narrated in the audio version by actress Michelle Williams, Britney recalls Justin getting incredibly “excited” when he ran into R&B singer Ginuwine.

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.’”

While explaining Justin Timberlake, 42, and Ginuwine’s run-in, Britney Spears described her ex-boyfriend’s successful boy band, NSYNC, as “white boys” who “loved hip-hop.”

“*NSYNC was what people back then called ‘so pimp.’ They were white boys, but they loved hip-hop. To me, that’s what separated them from the Backstreet Boys, who seemed very consciously to position themselves as a white group.”

“*NSYNC hung out with Black artists. Sometimes, I thought they tried too hard to fit in,” she adds.