Cry me a river: Why Justin Timberlake always soared while Spears and Jackson suffered

From Janet Jackson to Britney Spears, famous women in Justin Timberlake's gravitational orbit are seemingly sucked into his blackhole-like energy, ready to be eviscerated as his decades-long career grows and grows to undeniably indestructible heights. He’s been on the edge of a lot of scandal over the years, but has largely exited the situations unscathed as the women around him are left open to public blows. 

Spears, Timberlake’s childhood sweetheart, has mostly taken the brunt of his blatant and insidious misogyny. The pair first met in 1992 on the set of "The Mickey Mouse Club," when they were 11 and 12. In her explosive new memoir, "The Woman In Me," Spears said she had her first kiss with Timberlake during a game of Truth or Dare. They did not start dating until 1999 when Spears was 17 and they were together until 2002. When they were together, their short-lived relationship became a pop culture phenomenon, one that is still talked about today.

I mean, c'mon, they wore iconic matching Canadian tuxedos at the 2001 VMAs. 

However, in the book, Spears candidly shares that when she was 18, she had an abortion because Timberlake "wasn't ready to be a father." She said, “to this day, it’s one of the most agonizing things I have ever experienced in my life." 

"Justin definitely wasn’t happy about the pregnancy,” Spears wrote. “He said we weren’t ready to have a baby in our lives, that we were way too young." The decision was so traumatic for Spears that fans online are speculating that her poignant music video for the song "Everytime,” which features a scene of a mother who had just given birth meets her baby for the first time, was a symbolic way to memorialize this time in her life.

Spears also said in her memoir that if it was solely her decision, "I never would have done it. And yet Justin was so sure that he didn’t want to be a father." 

While this was happening privately, as the documentary "Framing Britney Spears" depicted, the public was hellbent on making Spears live up to this impossible standard of the virginal Madonna "good girl." However, Timberlake swiftly opened a barrage of slut-shaming for Spears after he revealed in an interview that he had sex with Spears, who had previously told the press she was waiting for marriage. When the couple broke up, the public sided with Timberlake because he released the explosive "Cry Me a River." The breakup-revenge song and music video is about a cheating partner whom people speculated was meant to be Spears. The video even stars a woman who looks eerily like Spears (whom Timberlake creepily watches as she showers). 

Of course, this blew up Spears' reputation in the celebrity-obsessed, women-hating tabloid media culture at the height of the aughts.

Timberlake successfully weaponized the song and video to implicate Spears in the demise of their relationship, all while she was privately dealing with the difficult emotions surrounding her abortion and the loss of a relationship. While he was at the top of the industry— earning a Billboard No. 1 song and winning a Grammy — Spears was being grilled by the media, infamously including Diane Sawyer, for causing Timberlake “"so much pain." 

Next up in the line of fire is icon Janet Jackson and the “nip slip seen around the world” (or at least by the audiences of the 2004 Super Bowl halftime show). While Timberlake and Jackson were performing, he reached across her chest and ripped off a section of her bustier to reveal her breast. Following the incident, which caused an immense amount of public backlash against Jackson, she said that it was planned ahead of time. But that did nothing to alleviate the vitriol directed at her. She lost her record label deal, movie deals and sponsors, as the documentary "Malfunction: The Dressing Down of Janet Jackson" reveals. She was even banned from the Grammys.

Timberlake finally publicly apologized to both Spears and Jackson, but not until after the Spears documentary dropped in 2021. 

“I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism,” he said. “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. Because of my ignorance, I didn’t recognize it for all that it was while it was happening in my own life, but I do not want to ever benefit from others being pulled down again.”

The apology was a nice little PR move to placate the rabid stans that were calling out Timberlake for his rampant misogyny, but it's not nearly enough to rectify and atone for the damage that has followed Spears and Jackson after their relationships and interactions with Timberlake. The only public pressure Timberlake faced was at the hands of fans who demanded respect for Spears and Jackson; for the most part, I find celebrity apologies to feel disingenuous because it seems like they are mostly done to save face as online warriors wait ready with their pitchforks and #JustinTimberlakeIsCanceledParty tweets.

Timberlake is still one of the most successful male pop stars in music. He produces hits for hyper-visible, chart-dominating, and pop culture-shaping Black women like Beyoncé and SZA and nobody bats an eye. He's even recently reunited with his NSYNC band members using the nostalgia train to sell a new song for the "Trolls" soundtrack, which Timberlake produced. The industry has never faltered with their support of Timberlake, while that certainly hasn't been the case for Spears. 

She suffered amid the onslaught of media exploitation and misogynistic abuse from men like Timberlake and her father, Jamie Spears who locked her in a 13-year-long conservatorship. Jackson literally was blacklisted in the music industry for something that Timberlake did to her. In Timberlake's own words: "The industry is flawed. It sets men, especially white men, up for success. It's designed this way."

Let's note it took him about 20 years to publicly apologize for behavior that he and his team of publicists and managers played into for decades. The reputational downfall of Jackson and Spears only made his star shine brighter. Even accusations that he cheated on his now-wife and actress Jessica Biel in 2019 haven’t  quite dimmed it. 

Timberlake was seen holding hands with one of his co-stars, which he called a "strong lapse in judgment." 

“But let me be clear – nothing happened between me and my co-star,” he said. 

As we have a public reckoning with the misogyny weaponized at female celebrities like Spears and Jackson, we mustn't forget Timberlake's role in it all and how he has always seemingly been able to reinvent himself as a man who now knows better. Those are always the most dangerous ones.