The Truth About Janet Jackson And Justin Timberlake's Complicated Relationship

To fully understand what happened at the 2004 Super Bowl halftime show and after it, you also need to know the truth about Janet Jackson and Justin Timberlake's complicated relationship. On professional and personal levels, the two superstars had an established accord that stemmed all the way back to the late '90s.

Sure, the two were hardly besties. But they appeared to share a mutual respect for one another and a bond deep enough that the fallout from what would become known as "nipplegate" was more devastating than anyone had perhaps anticipated. While much of America clutched pearls at the sight of a bare breast on live TV, others didn't understand the fuss. The artist formerly known as P. Diddy, for instance, told The New York Times that he was just happy his "three sons ... were able to see one of Janet Jackson's breasts in their lifetime." Either way, the response didn't seem welcome to those involved. 

People had a lot to say — but few, if any, initially seemed concerned about how Jackson felt about having her body accidentally exposed on live television. Between her career and Timberlake's, the emphasis seemed focused solely on damage control and contrition. But what happened to the relationship at the heart of the scandalous performance? Ensure your wardrobe is functional and keep those dance moves strictly PG-13 because this is the truth about Jackson and Timberlake's complicated relationship.

At the tail-end of the '90s, NSYNC had yet to establish itself as a boy band capable of tearin' up the hearts of teen girls across the U.S. As outlined in a Rolling Stone profile from 1998, the boy band found great fame in Europe before their home country welcomed them. So, when Janet Jackson invited them to open for her on "The Velvet Rope Tour," it marked the beginning of a new era for the pop act — suddenly, they were legitimate: They had the queen's approval. 

Speaking to MTV News about the tour, Justin Timberlake awkwardly suggested that he was "psyched" to be joining the superstar because, understandably, he was a total fanboy. "About two to three years ago I had her poster on my wall," he said. Three years later, when the members of NSYNC were finally huge stars in the U.S. in their own right, Timberlake paid tribute to Jackson onstage during her "MTV Icon" television special. Did he compliment her talent? Her influence? Her sound? Not quite.  

Instead, Timberlake jokingly interrupted bandmate Chris Kirkpatrick during his earnest tribute to the legendary artist by repeatedly reminding everyone that, on the babe-scale, Jackson is "fine." It was seemingly meant to be a cute, goofy bit — a sentiment that horny teenage boys the country over could sign off on — but it certainly hasn't aged well, even if Jackson was shown laughing it off at the time.

In 2002, a year after Justin Timberlake publicly glazed the "MTV Icon" award show stage with his own drool for Janet Jackson, the "Sexy Back" singer was newly single and being romantically linked to the "Nasty" hitmaker. 

According to the New York Post (via ABC News), the "unlikely pairing" was spotted "making out in front of everybody" at Missy Elliott's birthday party. Weirder still, Jackson's future partner Jermaine Dupri was named by the publication as being an eyewitness who spotted the two "bumping and grinding together in an L.A. club." Tabloids lapped up the rumor, with outlets including Star (via Pop Dirt) spreading gossip that Timberlake got "dumped" by Jackson "after a month of steamy-hot sex marathons." 

Naturally, the rumors went unverified and were probably best taken with a pinch of salt. Especially since a few months after the rumors emerged, so, too, did an actual announcement: Jackson was confirmed to be a guest performer on Timberlake's first solo album, "Justified." Singing on the track "(And She Said) Take Me Now," Jackson's "breathy vocals" were described by MTV News at the time as making "the track sizzle with extra sensuality." The timing was perfect. Who didn't want to hear the rumored chemistry between these two played out in a sexy duet?

By 2004, the apparent chemistry between Janet Jackson and Justin Timberlake was still a bed of scorching hot embers that could be poked whenever either of them needed a promotional push. Ahead of her much-hyped Super Bowl performance, Jackson was keeping the guest appearance of her rumored former paramour a secret. Timberlake's surprise reveal was set to be a headline grabber — but it became known for grabbing other things, instead. 

Prior to the live broadcast, Jackson's choreographer Gil Duldulao even teased to MTV News that there were "some shocking moments" to look forward to during the halftime show. They were an unfortunate choice of words, given what would come to transpire at the actual event and the furor that it would cause. So much so that MTV — who produced the halftime show — even had to add an editor's note to the news item to reassure people that they weren't somehow in cahoots with the great bra heist of 2004. 

"MTV thought that the 'shock' was going to be the as-yet-unannounced appearance of Justin Timberlake," they wrote, and added — in language so panicked that you can practically hear the anxious sweat dripping onto the keyboard — that the "subsequent performance was not what had been rehearsed, discussed or agreed to with MTV." So what happened?

After an entire song's worth of bumping and grinding to "Rock Your Body," Janet Jackson and Justin Timberlake brought the Super Bowl halftime show — and America with it — to an abrupt halt with one clean rip of fabric. After dropping his suggestive lyric, "Bet I'll have you naked by the end of this song," the "Justified" singer pulled off the cup of Jackson's bustier, exposing her breast. The live feed immediately cut away from the two performers, and chaos ensued. 

According to a statement released by a representative of the "Rhythm Nation" performer to E!, the incident was the result of some faulty engineering of Jackson's garment. "Justin was supposed to pull away the rubber bustier to reveal a red lace bra," they explained, however, "The garment collapsed and her breast was accidentally revealed."

According to The New York Times documentary "Malfunction: The Dressing Down of Janet Jackson," Jackson was described as crying backstage in a blanket following the incident. She then reportedly "fled" back to Los Angeles without speaking to anyone (via Today). Though Timberlake was described as being apologetic backstage, in front of cameras, the singer was all swagger. In a post-show interview with Access Hollywood, he quipped, "We love giving y'all something to talk about"(via Glamour). Quite. 

Backlash regarding the Super Bowl incident arrived quickly and heavily — and also disproportionately. MTV levied the blame squarely upon Janet Jackson, with the network's chief executive Tom Freston telling Reuters that she "engineered" the breast-baring incident. He also suggested that Justin Timberlake was only "informed of the stunt" right before taking to the stage, as though the pop star were some naive, sacrificial virgin to the gods of bad publicity (via People).

Meanwhile, an investigation into whether the entire performance violated indecency standards was being undertaken by the Federal Communications Commission. As reported by The Washington Post, "each of Viacom's 200 owned and affiliate stations" was facing penalty fines of up to $27,500, and both Jackson and Timberlake were also facing potential penalties as individuals. Though it took two to do the torn-top tango, the stars apologized as individuals rather than as a duo. 

Timberlake broke his silence first by issuing an apology for "the wardrobe malfunction," which he assured audiences "was not intentional and is regrettable," per MTV News. A day later, Jackson issued her own apology, which confirmed that the "costume reveal" decision was "made after final rehearsals." Sadly, it went wrong. "It was not my intention that it go as far as it did," she said, according to Entertainment Weekly. "I apologize to anyone offended."

Despite all attempts at apology, the great raging bus of outrage continued to burn rubber through the entertainment industry — and Justin Timberlake appeared to waste no time in throwing Janet Jackson under it. In an interview with KCBS (via The Washington Post), the "Cry Me a River" star suggested that Jackson and her choreographer had called him right before the show telling "him to rip her bra off" during the performance. When he carried out the alleged plan during the live broadcast, he was subsequently "'shocked and appalled' to discover a breast underneath."

What exactly the singer expected to find under there is anyone's guess, but regardless, Timberlake's apparent innocence had been seriously sullied. The incident had also, apparently, scuppered a perfect year. "I'm frustrated at the whole situation," he told the radio station, "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." This one career blip aside, he'd continue to enjoy a really good year. But Jackson? Not so much. For one thing, a spokesperson for the performer told Variety (via Entertainment Weekly) that she lost out on a starring role in a Lena Horne biopic because Horne was so upset about the Super Bowl incident.

Despite rumors that both Janet Jackson and Justin Timberlake were to be banned from the 2004 Grammy Awards due to their apparent professional misconduct at the Super Bowl, only one of them wound up "cut" from the ceremony. Ahead of the show, insiders told The New York Times that Jackson "would either step down herself or be asked to step down." And she was, indeed, absent at that year's awards ceremony.  

According to Entertainment Weekly, the "Together Again" singer had refused an opportunity to deliver a public apology at the event, which was why she wasn't invited to attend. Timberlake, meanwhile, accepted the conditions of his attendance and delivered yet another apology in the middle of his acceptance speech for winning the best male pop vocal performance Grammy for "Cry Me a River." "It's been a rough week on everybody," he said, as if Jackson's bare breast had ruined lives the country over, before once again reaffirming the "unintentional, completely regrettable" nature of the incident. 

And that was all it took. Timberlake was seemingly forgiven, while Jackson was left out in the cold. 

While Justin Timberlake's career appeared to be back on track — including his apparently bulletproof $6 million deal with McDonald's (via People) — Janet Jackson's had hit a major obstacle. As reported by Today, her 2004 album, "Damita Jo," was a commercial failure in comparison to her previous records, and it further received a mixed response from critics, the most cynical of which conflated the controversy of the Super Bowl incident with the unpopular tone of the record.

The Washington Post, for instance, accused "Damita Jo" of being "humid with sex" — something which they argued served as too much of a reminder "of the publicity stunt" prior. "Like getting naked on network television," they griped, "'Damita' has about it a hint of desperation." With Timberlake surviving the backlash relatively unscathed, he took the opportunity to finally speak out about the unequal treatment he'd received compared to Jackson.

"I probably got 10% of the blame," he admitted during a 2006 interview with MTV News, "And that says something about society. I think that America's harsher on women, and I think that America's unfairly harsh on ethnic people." Indeed. But as the years went on, did Timberlake ever use his self-acknowledged privilege to support Jackson during her career struggles? Apparently not. And as the "What Have You Done For Me Lately" star would go on to allege, she and Timberlake didn't speak to one another following the incident.

During a 2018 appearance on "The Oprah Winfrey Show," Janet Jackson opened up about the Super Bowl incident and didn't bite her tongue when it come to the disparity of blame. "All the emphasis was put on me, not on Justin," she said, before suggesting that their relationship may have been changed by the event. Though the superstar clarified that she still considered Timberlake "a friend," she also pointed out that they hadn't spoken since the show, and she may have had her reasons for that. 

"Justin has reached out, [but] we haven't spoken," she said, further explaining, "Friendship is very important to me, and certain things you just don't do to friends. ... In my own time, I'll give him a call." The "Ms. Jackson, if you're nasty" icon didn't clarify what exactly those "certain things" were, but she did reveal that she'd heard about remarks Timberlake allegedly made about the incident and also appeared to agree with Winfrey's sentiment that he had left her "hanging." 

Naturally, there were rumors that Timberlake wasn't thrilled with Jackson's statements. Per a 2006 Today report, fans became convinced that the former boy band star referenced the Oprah interview in Timbaland's tune "Give It To Me," which seemed to be a snide takedown of Jackson. The star set tongues wagging when he sang, "I saw you tryin' to act cute on TV/Just let me clear the air/We missed you on the charts last week/[Bleep] that's right, you wasn't there" (via Genius). Classy.

It took him over a decade, but by 2018, Justin Timberlake appeared to show some better understanding of the situation with Janet Jackson and his role in it. In a Beats 1 interview with Zane Lowe, the musician and "Southland Tales" star reflected on his mishandling of the situation. "I had my wires crossed," he said. "It's just something you have to look back on and be like: 'Well, okay, you can't change what's happened, but you can move forward and learn from it." 

Most importantly, perhaps, the star also alleged that he and Janet had finally resolved their issues and made peace. "I don't know that a lot of people know that," he added, explaining that he didn't consider it his "job" to inform the public of such things. He might have kept these reforged positive vibes between himself and Janet private, but that wasn't to say he wouldn't still reference the incident in public. And after his Beats 1 interview, a Jackson family insider told the New York Post that Janet still didn't "trust" Timberlake and hadn't "gotten past how he didn't man up."

In 2018, it was finally time for Justin Timberlake's go on the big Super Bowl halftime show ride, and it seemed like all that anyone could talk about was whether he'd be saving a seat for Janet Jackson. Prior to his big performance, the New York Post even reported that Janet's father, Joseph Jackson, thought it necessary for Timberlake to make things right at the event. "If he's such a gentleman, he'd make sure Janet [Jackson] is there," he told the newspaper. 

The following day, however, Janet shut down all hope of her attendance at Timberlake's halftime show by making her position clear on Twitter. Putting her feelings as simply and brusquely as possible, the superstar wrote, "To put to rest any speculation or rumors as to whether I will be performing at the Super Bowl tomorrow: I will not" (via Refinery 29).

As reported by Time, Timberlake nonetheless committed "a subtle acknowledgment" of the "nipplegate" incident without Janet's involvement. Singing "Rock Your Body" — the tune which soundtracked the original bustier-busting brouhaha — the singer precipitously shouted, "Stop!" right before the original offending lyric about getting naked, which was formerly followed by Timberlake jettisoning Janet's bra cup right off her body. 

In 2021, Justin Timberlake was forced to re-evaluate his behavior within the black mirror of the media. With the release of two New York Times documentaries focused on the mistreatment of Britney Spears and Janet Jackson during the early '00s, the superstar not only appeared to consider his contributions to such culture, but also his gains from it.

In an Instagram post shared at the start of the year, Timberlake apologized to both Spears and Jackson — whom he described as having "failed" — and acknowledged there were moments where he "spoke out of turn, or did not speak up for what was right." "I fell short in these moments," he wrote, "and benefited from a system that condones misogyny and racism."

It seemed to be a sincere and appropriate statement. However, it was slightly undermined by the behavior of Timberlake's manager, Johnny Wright, just a few months later. Seemingly a little bitter about Jackson not publicly acknowledging his client's statement, Wright reportedly wrote a comment on an Instagram post where Jackson urged her followers "to love, not to hate." As reported by The Mirror, using Timberlake's account, Wright wrote, "You should take this advice and to apply it to your relationship with Justin."

The comment was apparently deleted, with a source later suggesting to Page Six that "Justin was not aware" that his manager had written and posted it. 

In 2021, renewed attention given to the treatment of Janet Jackson in the aftermath of the 2004 Super Bowl halftime show potentially arrived a little too late for the superstar to care. Following the premiere of "Malfunction: The Dressing Down of Janet Jackson," for instance, the singer continued to maintain her dignified silence on the matter.

Amid the public outcry, though, she did take to Twitter to share a cryptic statement urging people to be kind. "Not sure if you got the memo," she wrote." But, we're not competing anymore, we're appreciating and uplifting each other instead." Whether or not the artist was talking about those involved with the Super Bowl incident may remain a mystery. What is certain, however, is that she wasn't exactly in support of the documentary in question. 

According to Jackson's former stylist — and the designer of her Super Bowl costume — Wayne Scot Lukas, the superstar asked him and others not to contribute to it. He told Page Six, "She wants to tell her own story," and added that she wasn't exactly cool with "Malfunction" existing. "She didn't ask for a 'Free Janet' documentary," he said. "She's not interested." 

It's unclear where Jackson and Timberlake's friendship currently stands. But whether they've made lasting peace and rekindled their platonic affection for one another will likely continue to go unseen from the public eye. After so much attention given to the two of them, maybe they both deserve some privacy.