The Shady Side Of Britney Spears

Britney Spears has always been stronger than she gets credit for; her ability to keep throwing shade despite everything she's been through is evidence of her resilience. After Britney's conservatorship was terminated and she finally got to say that it's nothing but her way, her parents found themselves on the receiving end of her Instagram wrath. In a since-deleted post, she accused her mom, Lynne Spears, of playing dumb about her conservatorship plight and attacked the intelligence of her father, Jamie Spears. "So take your whole 'I have NO IDEA what's going on' attitude and go f*** yourself !!!!" she wrote (via Uproxx). "You know exactly what you did ... my dad is not smart enough to ever think of a conservatorship."

Since gaining her freedom, Britney has released a memoir that has given her fans so many shady takes on key moments in her life. In one passage, the singer uses a classic Southern insult to dump on her ex-husband, Kevin Federline, and his failed attempt to make it big as a rapper. "Bless his heart — because he did take it so seriously," she writes in "The Woman in Me." Britney has also dissed quite a few people via her constant Instagram updates. In the caption of a throwback photo with Ben Affleck, she suggested that a purported snog with the actor was totally forgettable until she saw the old pic. "I made out with Ben that night ... I honestly forgot," she wrote (via USA Today). But this was hardly her shadiest moment.

How do you make Justin Timberlake cry a river? According to Britney Spears, you just have to school him on the basketball court. It might seem wild that these two haven't been able to completely bury the hatchet after all these years, but Spears has accused Timberlake of wounding her deeply. In her heartbreaking memoir, she claims that he pressured her to get an abortion and later dumped her via text.

Timberlake did such a number on Spears that she's been shading him since the early aughts. In a 2003 Rolling Stone interview, she shared her thoughts about Timberlake's diss track about her, "Cry Me a River," and the music video that infamously stars a Spears doppelganger. "I think it looks like such a desperate attempt, personally. But that was a great way to sell the record," Spears said.

Fast forward 20 years. After Spears dropped her memoir, Timberlake prefaced a performance of "Cry Me a River" with a pointed remark that seemed directed at his ex. "I'd like to take this opportunity to apologize to absolutely f**king nobody," he said. After he committed this personal foul on his ex, she stepped up to the free-throw line and responded with a social media swish. Spears didn't mention him by name but seemed to have Timberlake's basketball game in mind when she wrote on Instagram, "I never mentioned how I beat him in basketball and he would cry ... no disrespect!!!"

Britney Spears risked rekindling her beef with fellow bubblegum pop princess Christina Aguilera in 2022. It became evident that the two singers weren't exactly besties in 2003 when they traded barbs during separate interviews with Blender magazine. Aguilera described Spears as being "like a lost little girl" during rehearsals for that iconic MTV Video Music Awards kiss between the two of them and Madonna. Spears fired back by saying that the "Genie in a Bottle" singer rubbed her the wrong way with an unwanted kiss after two years of not speaking to her. "She comes up to me in a club in front of all these people and tries to put her tongue down my throat," Spears recalled (via Entertainment Weekly). She added that it was Aguilera who was the real "lost girl."

In a 2021 post on her Instagram Story, Spears shared her disappointment over Aguilera abruptly ending an interview after she was asked about Spears' conservatorship. However, Aguilera had first expressed her happiness for Spears. Months later, the "Toxic" singer seemed to body-shame Aguilera's backup dancers and possibly the "Dirrty" singer herself when she wrote on Instagram, "If I had Christina Aguilera's dancers I would have looked extremely small," according to Page Six. She made it clear that she was not referencing the dancers' height by also posting this Rodney Dangerfield quote: "I found there was only one way to look thin: hang out with fat people."

Britney Spears' family feud has raged on for years. Britney often uses Instagram to air her grievances with the rest of the Spears clan, and some of her most scorching social media slams have been directed at her sister, Jamie Lynn Spears. This may be because Jamie Lynn is also active on Instagram. In 2021, Jamie Lynn captioned a post, "May the peace of the Lord be with you, and your spirit," as noted by Page Six. Britney seemed to fire back with her own caption reading, "May the Lord wrap your mean a** up in joy today." The siblings both later edited their posts, but not before fans realized that a caption catfight had taken place.

After Jamie Lynn released her memoir, Britney took another swipe at her younger sister. She accused Jamie Lynn of using her to become a best-selling author in a since-deleted IG post that read in part, "I wish the almighty, Lord would could come down and show this whole world that you're lying and making money off of me!!!! You are scum, Jamie Lynn," (via E! News).

When Britney released her own memoir, she had more harsh words for her sibling. She described Jamie Lynn as being "a total b***h" when she was younger, painting a picture of the "Zoey 101" star as a spoiled child whose eyes were always glued to the TV. She also claimed that Jamie Lynn was ungrateful for the nice house she got to live in — courtesy of Britney.

When "Stranger Things" star Millie Bobby Brown appeared on "The Drew Barrymore Show" in 2022, she said that one of her biggest dream roles is playing Britney Spears in a biopic. Brown explained that she feels a sense of kinship with the "Baby One More Time" singer because they both grew up in the spotlight. "When I look at pictures of her, I feel like I could tell her story in the right way and hers only," she said.

While a Spears biopic has the potential to be a huge hit, the singer took to Instagram to inform Brown that she would get the opportunity to tell her life story over her dead body. "I hear about people wanting to do movies about my life ... dude I'm not dead!!!" she wrote. "Although it's pretty f***ing clear they preferred me dead." She'd previously mentioned her parents, so the latter half of that statement seemed to refer to them.

Of course, Spears could sign off on an authorized biopic while she's still alive if she wished to, so it's a shame that she doesn't want to give Brown her blessing to play her. The Brit actor has battled demogorgons and lived to tell the tale, so for her, recreating Brit Brit's iconic 2001 MTV Video Music Awards performance with a snake would be a piece of cake.

In the early aughts, Simon Cowell made a bold declaration about the song that launched Britney Spears' pop career. Speaking to Entertainment Weekly, he claimed that any vocalist could have recorded "Baby One More Time" and had the same success. It's unclear whether Spears knew about this remark when she shared her opinion of Cowell's critical feedback for "American Idol" contestants, but she made it clear that she was not a fan. In a 2003 interview with ITV (via Entertainment Weekly), she described how she would react if she were an "Idol" hopeful receiving feedback from Cowell: "I would take his advice and whatever he said and tell him to shove it." Years later, Spears got the opportunity to witness Cowell delivering his scathing critiques in person when she joined him at the judges' table on "The X Factor."

Regarding Cowell's "Baby One More Time" barb, it turns out that he had a reason to feel bitter about Spears recording the song. In a 2022 appearance on the "Howie Mandel Does Stuff" podcast, he revealed that he had tried to bribe the track's songwriter, Max Martin, to give him the song by offering Martin a Mercedes. Cowell wanted the song for his boy band Five, but Martin told him that he'd promised it to Spears. Cowell recalled telling Martin, "Let me give you some advice. No one is gonna have a hit with a name called Britney Spears."