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Justin Britney Getty 1.jpg

The Many Ways Justin Timberlake Spent Years Slut-Shaming Britney Spears

By Kayleigh Donaldson | Celebrity | October 18, 2023 |

By Kayleigh Donaldson | Celebrity | October 18, 2023 |


Justin Britney Getty 1.jpg

The upcoming release of The Woman in Me, the memoir of Britney Spears, is undoubtedly one of the most hotly anticipated moments in pop culture of the decade so far. Following the end of her conservatorship, her marriage and divorce, and her continued battles against the press and online conspiracy theorists, Spears is finally getting her moment to tell her truth with no strings attached. Leading up to this release, we heard whispers that various figures from Spears’ past were concerned about what she would disclose. Justin Timberlake, the singer who famously dated Spears when they were both in their late teens and early twenties, was said to be especially concerned. After a People Magazine excerpt from the memoir revealed that Spears had an abortion, it wasn’t hard to see why Timberlake was worried.

Spears’ book notes that Timberlake ‘said we weren’t ready to have a baby in our lives, that we were way too young’, even though she had wanted to have the child. They were both about 19 at the time. Spears continues, “To this day, it’s one of the most agonizing things I have ever experienced in my life.’ The discourse around this has, of course, been explosive. Reproductive freedom is a right so often stripped from us, and it’s something Spears was forced to deal with throughout her conservatorship as she was fitted with an IUD she did not want. Responding to accusations of coercion on this matter was never going to be easy for Timberlake. Instead, a ‘source’ told Entertainment Tonight that Timberlake and his wife Jessica Biel were ‘focusing on his own family and trying not to concern himself’ with Spears’ book. ‘Justin and Jessica just want everyone to grow and evolve instead of continuing to bring up the past.’ Well, if we’re talking about people who won’t stop bringing up the past, perhaps we should reacquaint ourselves with how Timberlake spent literal years dragging Spears through the mud for his personal and professional gain.

It’s not merely that Timberlake bragged about his sex life with his ex-girlfriend, which is depressingly typical bro behaviour, it’s that he turned it into a strangely crucial part of his brand as a solo singer, actor, and Jack of all trades. One of the reasons Timberlake endured post-NSYNC in a way that his fellow bandmates didn’t was that he had a lot of fingers in a lot of pies. He did music, movies, TV presenting, and a few too many SNL skits. He stridently played the game and gave the people what they wanted. As a former child star who grew up under the pressure of both Disney and Lou Perlman, he knew how to play the game, and that the rules were very different for men compared to women. He’s a player, she’s a slut. We’ve all seen that dichotomy play out time and again. So, when reinventing himself as an ice-cool stud who brought sexy back, it proved beneficial to occasionally throw Spears under the bus. And he did it a lot.

In a radio interview with Star and Buc Wild from 2002, when Timberlake was getting ready to sell himself as a solo singer fully, he was asked by the shock jocks if he had had sex with Spears. After initially playing the faux-private part, he laughed, ‘Okay, yeah, I did it […] I did it. I’m dirty. I’m in so much damn trouble, man. I’m going to get calls from my mother!’ In 2006, while being interviewed by the notoriously nosey Barbara Walters, he burst out laughing when she asked if Britney had ‘kept her promise to wait until marriage.’ He also confirmed the obvious when noting that his song ‘Cry Me a River’ was inspired by Spears allegedly cheating on him, saying, ‘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. I used my mind. I came up with a song.’



‘Cry Me a River’ is often considered one of Timberlake’s best songs. Rolling Stone included it on their 500 Greatest Songs of All Time at 484. It won the Grammy Award for Best Male Pop Vocal Performance and peaked at number three on the US Billboard Hot 100. It’s a scorched-earth break-up number, about a man kicking his girlfriend to the curb after she cheated on him. While Timberlake initially played coy on who the song was about, telling MTV News, ‘I will say writing a couple of songs on the record helped me deal with a couple of things’, he dropped that line rather quickly. As well as telling Walters the song’s origins, he admitted in a 2011 interview that he’d written the song after an argument with Spears (the rumour was that she had slept with Fred Durst.)



If the subtleties of Timberlake’s quotes weren’t enough to put two and two together, the music video certainly was. Director Francis Lawrence said, ‘There was just this unspoken agreement between [Justin and I]. Because [Justin and Britney] were on the same label; that’s part of the reason I thought the label would never, ever go for it. It was all about implying certain things, there’s little elements and details that play throughout [the video] and tie it in.’ Said references include a woman who looks quite a bit like Spears wearing a newsboy hat, as she often did at the time. Everyone knew who it was supposed to be. In a 2006 issue proclaiming Timberlake the International Man of the Year, British GQ declared that the video helped to make Timberlake ‘cool’ and reinvent him from Disney teenybopper to the ‘Trousersnake.’

When Timberlake became an exhaustingly regular feature on Saturday Night Live, the jokes and shaming continued. In a 2009 sketch, where Timberlake and Andy Samberg played their immigrant ancestors moving to America, Timberlake’s character imagined the bright future of his descendant (himself). ‘He’ll date a popular female singer. Publicly, they claim to be virgins but, privately, he hit it.’ Cue laughter. In 2009, Spears was thoroughly under the conservatorship that would plague her life for 13 years.



Timberlake was hardly the first person to use his famous romance to revive his image, but for many of my generation, he was the first to do it so publicly and successfully, all while the woman involved faced the brunt of the damage. Spears was barely out of her teens when the break-up occurred and was barraged with endless slut-shaming by the press. She was often seen as the epicentre of the country’s infamous double-edged sword approach to adolescent girls: endlessly leered over and commodified for their maturation yet slammed as whores and temptresses by the same people making money from their bodies. A 16-year-old girl in pigtails and a sexy schoolgirl outfit became the battleground for the era’s hypocrisies, and she was clearly not prepared for it. How could any teenager be? To be sold as the ultimate sex symbol while simultaneously reassuring the world that you’re saving yourself until marriage was supposed to reassure those perverts. It just set up a vulnerable young person to fail. That her boyfriend, the one she actually had sex with, helped to fling her under the bus must have hurt.

Hijacking Spears’ own sexuality and supposed lies for his own purposes ended up being a savvy career move for Timberlake. He got to be the cool guy who seduced the world’s most beautiful women and not the dork with crispy curls in double denim. He successfully made the jump from child star to sex symbol and never had to deal with a decade-plus of think pieces wondering if his dancing was corrupting the nation’s youth. That shred of self-awareness shared via SNL skits also made him seem like he was in on the joke. Now, knowing said joke was at least partly rooted in prodding at Spears’ own pain following an abortion leaves a nasty taste in one’s mouth.

Spears spent a long damn time not being able to talk about her life, pain, or the ways she was ripped to shreds by the press. In hindsight, it is telling that, after suffering from one of the most public breakdowns of the 2000s, she didn’t give any tell-all interviews or forced apologies or any of the usual media rigmarole that was expected of the time. She just got on with life, or to be more accurate, she was forced to continue business as usual. Now, she gets to burn the bridges she was forced to build. If Justin Timberlake can’t take that after years of dishing it out? Well, cry me a river.