Britney Spears and Jamie Lynn Spears’ Ups and Downs Amid Conservatorship Drama: A Timeline

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Britney Spears and Jamie Lynn Spears' Ups and Downs Amid Conservatorship Drama: A Timeline

A dramatic relationship. Britney Spears and Jamie Lynn Spears have had a bumpy ride through the years — and haven't always kept that drama under wraps. In June 2021, the pop star spoke out in court for the first time since being put under a conservatorship in 2008. During the explosive hearing, she explained why she should be able to choose her own attorney, adding that she wanted to take legal action against her family. "I just want my life back. It’s been 13 years, and it’s enough. It’s been a long time since I’ve owned my money," the "Lucky" singer said at the time. "I would honestly like to sue my family, to be totally honest with you. I also would like to be able to share my story with the world, and what they did to me, instead of it being a hush-hush secret to benefit all of them." [sendtonews type="float" key="BVEFlYYlJU-2840550-14453"] Following the case, the Sweet Magnolias star responded to fans via Instagram who claimed she wasn't publicly supporting the #FreeBritney movement because she hadn't posted on social media. “Maybe I didn’t support her the way the public would like me to with a hashtag on a public platform, but I can assure you I’ve supported my sister long before there was a hashtag. And I’ll support her long after. Note that," the actress shared. "I’m so proud of her for using her voice. I’m so proud of her for requesting new counsel like I told her to do many years ago. If ending the conservatorship or flying to Mars or whatever else she wants to do [will make her happy] — I support that, 100 percent. Because I support my sister. I love my sister. Always have, always will. As long as she’s happy. Let’s keep praying. That’s all." In July 2021, the Grammy winner was granted the right to choose her own legal representative, appointing former federal prosecutor Mathew Rosengart in charge. At the time, she also accused her father, Jamie Spears, of "conservatorship abuse," adding, “If this isn’t abuse, I don’t know what is. … I thought they were trying to kill me.” Amid the hearings, Britney and her sister both shared their thoughts via social media.

While Britney has continued to assert her younger sister did not always have her back, Jamie Lynn tried to defend the pop star amid their challenging relationship.

“That love is still there, 100 percent. I love my sister,” Jamie Lynn said during a Good Morning America interview in January 2022. “I’ve only ever loved and supported her and done what’s right by her, and she knows that. So I don’t know why we’re in this position right now. ... I’ve always been my sister’s biggest supporter, so when she needed help, I set up ways to do so."

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Not on the Payroll

Following a report that claimed that Jamie Lynn is the only member of the Spears family not on Britney's payroll, the Zoey 101 alum responded via her Instagram Story. "Facts….now leave my broke-ass alone,” she wrote in July 2021.

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Slamming the 'People Closest' to Her

On July 16, 2021, Britney shared a quote via her Instagram that read, “Never forget who ignored you when you needed them and who helped you before you even had to ask.” In a lengthy caption, she explained what she is going through.

"There’s nothing worse than when the people closest to you who never showed up for you post things in regard to your situation whatever it may be and speak righteously for support … there’s nothing worse than that," the Crossroads star wrote. "How dare the people you love the most say anything at all. ... If you’re reading this and you know who you are … and you actually have the nerve to say anything about my situation just to save face for yourself publicly !!! If you’re gonna post something …. Please stop with the righteous approach when you’re so far from righteous it’s not even funny."

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My 'So Called Support System'

The "Toxic" singer shared a second quote the following day that read, “Take me as I am or kiss my ass, eat s–t and step on LEGOs.” After slamming those who make fun of her dancing videos, Britney called out both her father and sister. "I'm not gonna be performing on any stages anytime soon with my dad handling what I wear, say, do, or think I've done that for the past 13 years," she wrote. "I don't like that my sister showed up at an awards show and performed MY SONGS to remixes!!!!! My so-called support system hurt me deeply."

Credit: Courtesy of Jamie Lynn Spears/Instagram

Looking to the Lord

Jamie Lynn returned to Instagram on July 18, 2021, sharing a selfie of herself in the mirror. "May the peace of the Lord be with you, and your spirit," her caption read at first. She later changed the caption to a peace sign emoji and a heart emoji.

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A Sly Response

Shortly after Jamie Lynn's post, Britney posted a new dance video. "May the Lord wrap your mean ass up in joy today," she wrote, seemingly mocking her sister's original caption. "New dance … if you don’t like it ... don’t watch it!!!!!"

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Unfollowed

Britney only follows 46 Instagram accounts. While Paris Hilton, Paul McCartney and Beyonce made the cut — Jamie Lynn was notably absent. However, the younger sister still follows the pop star.

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Trading Barbs

Jamie Lynn opened up about her relationship with her older sister during a January 2022 interview with Good Morning America — and Britney was quick to turn the tables. Though the Netflix star claimed that she attempted to provide resources for her older sister to put an end to her conservatorship, Britney argued via Twitter that Jamie Lynn was "never around me much 15 years ago at that time."

As the family drama made headlines, Jamie Lynn defended herself in a lengthy social media statement. "I can't help that I was born a Spears too, and that some of my experiences involve my sister. I've worked hard since before I was even a teenager, and I've built my career in spite of just being someone's little sister," she wrote. "There are no sides, and I don't want drama. But I'm speaking my truth to heal my traumas, so I can close this chapter and move forward, and I wish my sister could do the same."

She concluded: "No matter what comes, I will always love my big sister and be here for her. It's time to put an end to the unhealthy chaos that has controlled my life for so long."

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Pleading for Privacy

Jamie Lynn responded to Britney in her Instagram story after the "Bombastic Love" singer walked back a few comments but still maintained that Jamie Lynn was lying.

“Britney — Just call me, I have attempted many times to speak to you directly and handle this privately like sisters should, but you still choose to do everything on a public platform,” the former Nickelodeon star shared via her Instagram Story in January 2022.

Jamie Lynn continued, writing, “In the meantime, please stop continuing the narrative that I haven’t been there for you or that I’m making things up. I’m happy to share how many times I’ve reached out to you, supported you and tried to help you. This is embarrassing and has to stop. Love you.”

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Britney Backtracks

After Britney implied that her sister was "scum," the Grammy winner walked back some of her jabs. "I said some harsh things because you obviously hurt me by the things you are making up about me,” she wrote via Twitter in January 2022.

“All I know is I love you unconditionally!!! So go ahead and say whatever you want … it’s so tacky for a family to fight publicly like this!!! You say you love me … yet your loyalty is still with the people that hurt me most!!!” the engaged singer added.

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Cease and Desist

Following the release of Jamie Lynn's memoir and her appearance on "Call Her Daddy" in January 2022, Britney's lawyer issued a strongly worded cease and desist to the actress, asserting that Britney will "no longer be bullied" by her family.

"Although Britney has not read and does not intend to read your book, she and millions of her fans were shocked to see how you have exploited her for monetary gain. She will not tolerate it, nor should she," the letter read.

Britney's attorney went on to threaten legal action, writing, "Michelle Obama famously said, 'when they go low, we go high,' and to Britney's great credit, that is exactly what Britney is going to do, for the time being. You recently reportedly stated that the book was 'not about her.' She takes you at your word and we, therefore, demand that you cease and desist from referencing Britney derogatorily during your promotional campaign. If you fail to do so or defame her, Britney will be forced to consider and take all appropriate legal action."

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Another Scathing Social Media Post

“Congrats best seller … I’m not surprised at all 👏🏼📚👎🏻 !!! The nerve of you to sell a book now and talk s—t but your f—king lying just like you lied about Alexa Nikolas !!!!” Britney wrote via Instagram in January 2022. “I wish you would take a lie detector test so all these masses of people see you’re lying through your teeth about me !!!! 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.”

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Baring It All

In March 2022, an insider told Us that Britney "will hold nothing back" in her memoir. Us confirmed one month prior that the "Unusual You" singer inked a multimillion-dollar deal with Simon & Schuster for a tell-all book. “Britney feels extremely betrayed by Jamie Lynn, as she has expressed publicly,” the source added. “She will lay out that without her, Jamie Lynn would have no career.”

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Slight Show of Support

After Britney announced that she was expecting a child with her fiancé, Jamie Lynn showed her support by "liking" the post on Instagram.

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Missing Britney’s Wedding

Us confirmed that the Things I Never Said author did not attend her big sister’s wedding ceremony to Sam Asghari in June 2022.

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Legal Response

In court docs obtained by TMZ in June 2022, Jamie requested for Britney to sit in on a deposition in order to challenge her claims on social media and in her upcoming tell-all memoir.

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Birthday Wishes

“It’s my b-day but you’re my heart so I’m thinking about you,” Britney wrote via Instagram on her 41st birthday, sharing a photo of Jamie Lynn. “Congratulations on being so brave, inspiring, and showing guts and glory in your show 🎉 !!! You ain’t alone … if anybody knows what that feels like … I get it 🤧🤧🤧 My baby sister !!! I love you !!!”

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'Still a Lot of Love'

After Britney raised eyebrows with her tribute to Jamie Lynn in December 2022, a source explained exclusively to Us, "Britney will always love her sister," adding that the sisters still share a bond.

“[Britney] goes back and forth about whether or not she wants to speak to her, but the bottom line is that there’s still a lot of love between them that will never go away," the insider told Us. "Jamie is heartened that Britney seems to be softening towards her, it’s a step in the right direction as she sees it."

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A Private Reunion

"It was nice to visit my sister on set last week !!! I’ve missed you guys so much !!! Loyal girls stay home but it’s so nice to visit family 😌 !!!" Britney wrote via Instagram in June 2023.

A source exclusively told Us at the time that the pop star was trying to start fresh with her loved ones.

"There have been some bumps in the road for Britney, but that's to be expected. She's feeling really positive about things, and she's hopeful about the future," the insider shared. "Britney's proud of herself. She's had a lot to adjust to, but she's taking things one day at a time and trying not to sweat the small stuff — even when it's a challenge."

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Jamie Lynn Tells Daughter to Be ‘Proud’ of Aunt Britney

Jamie Lynn opened up to Variety in July 2023 about the hardships her eldest daughter, Maddie, has faced at school due to Britney’s drama with the family. Despite the siblings’ ups and downs, Jamie Lynn revealed she tells Maddie, “’You should be so proud. Look at what your family’s done and accomplished. We came from a small town, and now everybody’s fascinated by the good and, especially, the bad. But look at what an example of a strong female you have. You have something to be proud of, and you should have pride in that.’”

The actress then gave an update on her dynamic with her big sister, saying, “I have nothing but absolute love for every single one of my family members. If I learned anything from last year, being so open and feeling like I had to defend myself at times, I don’t feel like there’s anything else that I need to say. I just have to leave it where it is because those conversations are meant to be personal.”

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Britney’s Tell-All Memoir

Britney’s October 2023 tell-all memoir The Woman In Me was filled with major bombshells, and also shed light on her rocky relationship with Jamie Lynn.

“Jamie Lynn clearly suffered in our family home, too. She grew up a child of divorce, which I did not,” Britney wrote. (Their parents split in 2002.) “But I don’t think she fully understands just how desperately poor we were before she was born. Because of the money I brought to the family, she wasn’t helpless in the face of our father, like my mother and I were back in the 1980s.”

While recalling their tumultuous relationship, Britney wrote that she became concerned with her sister’s behavior when she was still a child and referred to an 11-year-old Jamie Lynn as a “total bitch.” Britney specifically took issue with how her sister treated their mother, Lynne Spears.

Britney also revealed that she learned the news about her sister’s pregnancy via “an exclusive in the tabloids,” not from Jamie Lynn herself. “The family had kept it from me,” Britney alleges in her memoir, and said, “This was around the time that Jamie Lynn almost filed for emancipation from our parents.”

Britney also wrote about her sister’s lack of support during her conservatorship, with Jamie Lynn allegedly suggesting her sister “stop fighting” after she was placed in rehab by their father in 2018.

The pop star also recalled when Jamie Lynn pitched the idea of a “sister talk show” after Britney had returned from a mental health treatment facility. In the book, she wrote that she was “a shell of myself” and “still on lithium” when her “family walked into [her] house like nothing had happened.”