Britney Spears’s Latest Swipe At Justin Timberlake Proves That She’s Finally Defending Herself Against Unnecessary Digs — And It’s Been A Long Time Coming

From journalists’ invasive questions about her sex life to cruel comments made by Justin Timberlake, Britney Spears has long remained silent when it comes to handling criticism and digs. That is, until now.

Earlier this month, Britney Spears found herself at the center of public attention after she hit back at Justin Timberlake for making an apparent dig at her.

The drama between the exes — who dated between 1999 and 2002 — erupted out of nowhere, with Justin seemingly shading Britney at a concert shortly after she apologized to him and anyone else she’d “offended” in her 2023 tell-all memoir, The Woman in Me. She wrote on Instagram, “I wanna apologize for some of the things I wrote about in my book. If I offended any of the people I genuinely care about, I am deeply sorry,” before going on to name-check Justin by praising his recently released song, “Selfish.”

However, Justin quickly made it known that he wasn’t feeling quite as apologetic, declaring on stage at his show in New York days later that he had “fucking nobody” he wanted to say sorry to. And, seemingly as a result, Britney wasted no time walking back her apology the following day.

“Someone told me someone was talking shit about me on the streets!!!” she wrote on Instagram. “Do you want to bring it to the court or will you go home crying to your mom like you did last time??? I'm not sorry!!!”

As things unfolded online, several fans said it was “immature” of Justin to seemingly shade Britney for simply apologizing — especially given his notorious treatment of her after their 2002 split, which he eventually apologized for in 2021 after mass public criticism.

All while Justin perpetuated the negative portrayal of Britney in the press for years after they broke up, she largely remained silent — even after she was brought to tears in a grueling interview about their relationship.

With this in mind, Britney’s recent apparent response to Justin wound up sparking a wider conversation around her refreshing newfound courage when it comes to calling people out, with Vogue magazine publishing an article stating that she “shouldn’t have to apologize” given how long she’s put up with unnecessary digs and jabs.

Unlike Justin, Britney has spent years as a “punching bag” for tabloids, with fans pointing out that she’s endured “decades of bad press.” Away from invasive questions about Justin and their sex life, the ”Toxic” singer was scrutinized over almost every aspect of her personal life throughout the ‘00s — from her clothing choices, to her eventual divorce from Kevin Federline, to her parenting once she welcomed her two sons.

And even though Britney was as young as 17 when she was asked some of these inappropriate questions, she always bit her tongue and refrained from snapping back — something that continued for years and years, even after her controversial conservatorship came into effect in 2008.

To paint a clearer picture, here’s a breakdown of the ways Britney handled invasive questions and cruel criticism between the late ‘90s and ‘00s, compared with exactly how she’s started to defend herself in recent years.


Back in 1999, when Britney was 17, she was awkwardly questioned about whether or not she had breast implants during a TV interview with journalist Ivo Niehe.

Ivo mentioned that Britney’s breasts were something that “everyone” was “talking about,” before asking her what she thinks about “breast implants.”

Britney was seemingly caught off guard by the question, but replied: “I think if that’s what you wanna do, and that would make you happy, then I see nothing wrong with it. But I haven’t done that.”

Fast forward to 2023, and Britney called out the reporter — and wider public interest in her body — in her memoir. Although she didn’t address Ivo by name, she wrote, “Everyone kept making strange comments about my breasts, wanting to know whether or not I’d had plastic surgery.”


While Britney was inundated with questions about her body and sex life during her and Justin’s relationship, things only got worse once they split in 2002 after Justin infamously dragged her name in the press.

He fueled rumors that she’d cheated on him with the release of his breakup anthem “Cry Me A River,” which featured an uncanny lookalike of Britney in the music video, while later making several claims about their sex life. Appearing on The Star & Buc Wild Morning Show, Justin was asked, “Did you fuck Britney Spears? Yes or no? Come on, man.” He replied, “Oh, man. OK, I did it!” while people at the studio cheered loudly.

He was then asked if he’d had “oral intercourse” with Britney, to which he said, “I did it. I’m dirty. I’m in so much damn trouble, man.”

Britney ended up being vilified in the media as a result of Justin’s remarks, not least because she’d previously said she’d planned on abstaining from sex until she was married. But Justin seemingly didn’t care; the following year, he was asked by Barbara Walters if Britney had “kept her promise to wait until marriage, to which he infamously burst out laughing before replying, “Sure.”

As a result, Britney faced even more invasive questions and ongoing vilification over her sexuality. 

At the world premiere of her 2002 film Crossroads, one journalist asked then-20-year-old Britney, “You are not a girl, you are not yet a woman. What are you?” — referencing her 2001 hit song, “I’m Not a Girl, Not Yet a Woman.” The entire audience laughed out loud at the suggestive question — but Britney simply brushed it off and offered a “mature” response.

She said, “The song’s talking about growing up and coming into your own and finding yourself. ... Who’s to say what a woman or a girl is? What’s the definition of that? I’ve just learned that I am, and I’m just me. So, whatever that is.”

At the same press conference, Britney was also asked how she felt about the “constant speculation” around her virginity. In response, she gave an awkward smile and said, “I really wish I would’ve never said anything to begin with because I’m kinda stuck in this little place where people are always asking me. But you know that’s just part of growing up and that’s just something that we all have to deal with.”

However, Britney’s discomfort was immediately dismissed by the reporter, who followed up with: “Have there been any changes on that front?” The entire audience burst out laughing, but Britney stayed calm and replied with a smile: “That’s a personal question.”


By July 2003, Britney wound up telling W Magazine that she had in fact had sex during her relationship with Justin. She also clearly felt as though she had to present a palatable version of events and defend her decision to have sex with Justin, addressing his various invasive comments about their private life by saying: “I’ve only slept with one person my whole life. It was two years into my relationship with Justin, and 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.”

And later that year, in November, Britney sat down for one of her most infamous interviews to date, with Diane Sawyer.

Britney, who was 21, broke down in tears after being berated by Diane, who not only grilled her over her split from Justin, but also told the singer that former Maryland First Lady, Kendel Ehrlich, said she’d “shoot” her given the opportunity.

Although Britney was visibly upset throughout the interview, she didn’t snap. And it wasn’t until 2021 that she finally slammed Diane over the entire thing, later writing in her memoir that she felt she’d been “exploited” by the interview.


Fast forward a few years, and things had changed significantly within Britney’s personal life.

She began dating Kevin Federline in the summer of 2004, and by September that year, they were married. In Sept. 2005, they welcomed their first child, Sean Preston, followed a year later by their second son, Jayden James.

But sadly, this still didn’t protect Britney from scrutiny. In fact, she was faced with more critical comments about her personal life, her past, and now her parenting, too.

In June 2006, Britney made a now-infamous appearance on Dateline, where she was interviewed by controversial media personality Matt Lauer. During their chat, Matt grilled Britney on just about everything — from her and Kevin’s relationship, to any accidental mistakes she’d made as a new mom.

Once again, Britney remained collected throughout the grueling chat — even when Matt asked her about a time that she’d tripped while holding her baby boy. When Matt described the incident as a “close call,” Britney replied, “Accidents happen. Stuff happens with kids. It's reality. Unfortunately, not everybody has 80 cameras on them 24/7.”


Sadly for Britney, this scrutiny only continued the following year. When she appeared on Ryan Seacrest’s live radio show in 2007, seemingly to promote her studio album Blackout, Britney was instead faced with numerous questions about her parenting. Ryan asked her if she was doing all she could for her children, how often she saw them, and to comment on the negative media coverage of her parenting habits.

Fans even speculated that Britney had left the interview early as a result of Ryan’s harsh questions when it was revealed that she “ran” off into another room before saying goodbye. All the while, she didn’t bad-mouth him, and continued to appear on his show for years to come.

2008 - 2021

By 2008, Britney’s conservatorship had come into effect, meaning that her life and finances were legally controlled by her father, Jamie Spears, and a group of lawyers. This was the case until Nov. 2021, when the legal arrangement was finally terminated following a strenuous battle in court.

During the years that Britney lived under the conservatorship, her media appearances were tightly controlled, too. In 2016, Britney allegedly tried speaking out about her legal arrangement during an appearance on UK talk show The Jonathan Ross Show. But, she later claimed in her memoir that everything she’d discussed didn’t end up being aired.

Meanwhile, she largely remained silent when her personal battles were made public, too. In 2018, she famously found herself embroiled in a legal dispute with her now-ex-husband Kevin, who requested that she increase her monthly $20,000 child support payments to him. Kevin’s request infuriated fans across the globe, and while sources claimed Britney was “unhappy” behind-the-scenes, she never once bad-mouthed him at the time.

What’s more, Britney also stayed quiet as the #FreeBritney movement began to gain traction, which came about once fans started speculating that the singer was not OK.

Britney’s sister, Jamie Lynn, famously criticized the movement in April 2019 — a year after she’d quietly been made a trustee of Britney's estate. At the time, Britney didn’t say anything, although she’d go on to publicly criticize her sister years later once the legal battle to terminate her conservatorship began, in June 2021. Fans did speculate that Britney was quietly signaling for help via cryptic social media messages in the years before her court battle commenced. 

2021 also saw the release of FX’s Framing Britney Spears documentary, which brought to light the unsettling way Britney had been treated by the press throughout her life. The documentary had a profound effect on the public. They finally began to recognize how inhumane much of this treatment had been — as well as their own complicity in creating such a hostile media environment — and support shifted overwhelmingly in her favor.

This support, along with her aforementioned legal battle, gave Britney a bout of newfound courage to begin speaking out.

In June of that year, Britney famously denounced her entire family before a judge in court, accusing them of doing “nothing” to help while she’d been struggling under the terms of the conservatorship. And before long, the feud made its way onto social media, with Britney repeatedly slamming her mom, dad, and sister for their alleged involvement in her conservatorship.


This continued over the next couple of years, with Britney going on to denounce not just her family via social media, but anyone else who she felt had wronged her throughout her life. In March 2022, she called out Justin Timberlake for weaponizing her name to bolster his career in the early ‘00s. In April, she accused Kevin Federline of refusing to see her while she was pregnant — something that his lawyer hastily denied.


In 2023, Britney released her tell-all book, which saw her getting even more off her chest.

As well as her family and exes, Britney — who pointedly opted out of doing any TV interviews to promote the book and said that it’s “finally time” for her to use her own “voice” — slammed journalists who had scrutinized her throughout her career.

Calling out Diane Sawyer for asking her “harsh question after harsh question” in that infamous 2003 interview, Britney wrote, “I shouldn’t have been forced to speak on national TV, forced to cry in front of this stranger, a woman who was relentlessly going after me.”

She also slammed Ryan Seacrest over her aforementioned 2007 appearance on his radio show, writing, “Ryan Seacrest asked me questions like, ‘How do you respond to those who criticize you as a mom?’ and ‘Do you feel like you’re doing everything you can for your kids?’ and ‘How often will you see them?'”

“It felt like that was the only thing people wanted to talk about: whether or not I was a fit mother. Not about how I’d made such a strong album while holding two babies on my hips and being pursued by dozens of dangerous [paparazzi] all day every day,” she added.

In a similar vein, Britney frankly questioned why Matt Lauer had felt the need to inform her of all the negative press around her parenting during their interview. She wrote, “He said that people were asking questions about me, including, ‘Is Britney a bad mom?’ He never said who was asking them. Everyone, apparently.”

And Britney went on to call out Matt for seemingly shifting the blame onto her when discussing how she was constantly hounded by paparazzi. She wrote, “He asked me what I thought it would take for the paparazzi to leave me alone. I wished he’d ask them — so whatever it was, I could do exactly that.”

And this brings us to today, where it’s more clear than ever that Britney is in a new era of fiercely defending herself and calling out people who disrespect her — something that was undoubtedly made easier by the massive shift in societal attitudes towards women since the ‘00s, as well as the renewed criticism of the horrific way she was treated in the press. At last, Britney is able to use her voice without being completely vilified; since first speaking out, she’s been supported heavily not just by fans, but by other celebrities and major media outlets too. And it’s been a long time coming.

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