Britney Spears, 39, and her only sister Jamie Lynn, 30, have had their ups and downs over the years. With their nine-year age difference, Britney always had a close relationship Jamie in her younger years — but the nature of their dynamic changed throughout Brit’s on-going conservatorship. Look back at the two sisters timeline from their early years to now.
Britney and Jamie Lynn’s Early Days To Jamie Lynn’s On Screen Debut
Jamie Lynn was born on April 4, 1991 in McComb, Mississippi to parents Jamie Spears and Lynne Spears. The couple were already parents to Britney, their middle child who was 8, and son Bryan Spears, now 43.
Jamie Lynn got her first taste of the limelight in 2002 when she portrayed a younger Britney in the film Crossroads, and All That. “I love my little sister and I am overprotective with her, and I don’t mind saying that,” Britney said that same year to Access Hollywood. “My sister is a handful. We are so different. It’s so funny — actually, she would be a lot better in this business than I am. Like her personality, she is Miss Diva. She is so full of herself, it’s so cute,” she said.
Later that summer, the two sisters appeared on the Teen Choice Awards together in an unforgettable presenting moment. Brit came out to assist her then 11-year-old sister as she sweetly took to the mic to name Tobey Maguire as a surfboard winner.
Lucy Nicholson/AP/Shutterstock)
Jamie Lynn’s 1st Pregnancy & Britney’s Conservatorship Begins
Shortly after, Jamie Lynn was named the star of Nickelodeon’s Zoey 101 — a role which she held until she was 16 years old. The star abruptly departed the teen series in 2007 after becoming pregnant with her eldest daughter Maddie Briann Aldridge, now 13, with ex Casey Aldridge. The same year, Britney began experiencing her own struggles, leading to her infamous hair shaving moment ahead of the Blackout release. The conservatorship came into place by Feb. 2008.
Jamie Lynn Named Trustee In Britney’s Estate & Defends Her Relationship With Britney
While Jamie Lynn and Britney’s father Jamie remained conservator of Britney’s estate — which references her business assets and music holdings — Jamie Lynn was added as a trustee of her estate in 2018. The 30-year-old was reportedly appointed to the role to ensure that Britney’s assets were entirely devoted to the care of her sons Sean Preston, 16, and Jayden James Federline, 15, in the event of her death.
When the #FreeBritney movement began getting traction online in 2019, Jamie Lynn spoke out in support of Britney. Jame Lynn’s tweeted message came shortly after the popular Britney’s Gram podcast ran an anonymous audio message from an alleged paralegal who claimed to be working at the law firm overseeing Britney’s conservatorship. He alleged specifically that Britney was forced to check into a mental-health facility against her will, as well as confirmed theories that the hosts had pertaining to Britney’s legal situation.
“10 years ago, who was there??” Jamie Lynn began in the 2019 tweet, including a video of Britney being chased by paparazzi. “I have been here long before anyone else and I’ll be here long after…Don’t come for me or the ones I love anymore,” she added.
The movement lead to the film Framing Britney Spears, which explored Britney’s conservatorship through a timeline and series of interviews. It was believed that Jamie Lynn attended a #FreeBritney rally after the films’ premiere, which she denied.
“A few media outlets ran a false story about me attending a virtual rally yesterday,” she wrote via social media. “In fact, someone represented themselves as me without my knowledge. I love my sister very much, but I was not aware of the rally, nor was I in attendance for the virtual rally.”
Britney Says She Wants To “Sue” Her Family
While everything seemed good between Britney and her sister for the most part, things appeared to take a drastic turn following Britney’s first court testimony in June 2021 (she did a second in July). In her bombshell 20 minute statement, the Louisiana native made a number of accusations, saying she would like to “sue” her entire family (but didn’t name names). “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,” Britney also said.
Jamie Lynn Stands Up For Britney & Denies She’s Financially Benefitting From The Conservatorship
In the days after, Jamie Lynn once again took to social media to speak up — saying she was “proud” of Britney. “Since the day I was born, I’ve only loved, adored, and supported my sister,” she said about Spears. “I mean, this is my freaking big sister, before any of this bull—-,” Jamie Lynn penned. “I don’t care if she wants to run away to a rainforest and have a zillion babies in the middle of nowhere, or if she wants to come back and dominate the world the way she has done so many times before, because I have nothing to gain or lose either way.”
“I felt like until my sister was able to speak for herself and say what she felt she needed to say publicly, that it wasn’t my place and it wasn’t the right thing to do,” she also said. “But now that she’s very clearly spoken and said what she needed to say, I can follow her lead.”
Failed actress and Kids Choice Award Winner, Jamie Lynn Spears has posted an Instagram Story showing sudden support for her Pop Icon and Grammy Award Winning Sister, Britney Spears, days after her court hearing. Thoughts? pic.twitter.com/NheAwS5aH0
— Fan Account (@TheSpearsRoom) June 28, 2021
Amid allegations that Jamie Lynn was financially benefitting from the conservatorship, the former Nickelodeon actress also received death threats aimed at her and her children Maddie, 13, and Ivey, 3.
Jamie Lynn shared a screenshot of a news article titled, “Britney Spears’ sister Jamie Lynn shares photos of her home life…after it’s revealed she is the ONLY family member not on the singer’s payroll” via Instagram, with a strong message of her own. “Facts…now leave my broke ass alone,” Jamie Lynn added.
Once again, things seemed to be on decent terms between the sisters as Jamie Lynn posted that Britney had sent her two daughters toys. “Nothing sweeter than coming home to a box full of goodies for my girls from their auntie,” she wrote via IG.
Britney Posts A Cryptic Message Seemingly Aimed At Jamie Lynn
Eyebrows were raised, however, when Britney posted a lengthy message that was aimed at the people “closest” to her — but declined to name Jamie Lynn or any other family members directly. “How dare you make it public that NOW you CARE … did you put your hand out when I was drowning ???? Again … NO …,” Britney wrote.
“If you’re gonna post something …. Please stop with the righteous approach when you’re so far from righteous it’s not even funny,” she continued. The post has since been removed.
Britney Spears Officially Calls Out Jamie Lynn For A Past Performance
By July 17, 2021, Britney made it very clear that she did have an issue with Jamie Lynn. The pop star called out a 2017 Radio Disney Music Awards performance where Jamie Lynn performed remixed versions to some of Britney’s tracks, including her 2011 jam “Till The World Ends.”
“I don’t like that my sister showed up at an awards show and performed MY SONGS to remixes !!!!!” Britney wrote while explaining that she had been trying to make the music she wants to make for years to no avail due to the conservatorship. “My so-called support system hurt me deeply !!!!…[this] conservatorship killed my dreams,” she said at the time.
Britney & Jamie Lynn Appear To Exchange Instagram Jabs
The social media shade continued via Instagram captions. On July 18, Jamie Lynn posted a photo of herself writing, “May the peace of the Lord be with you, and your spirit” alongside a peace sign and heart emoji.
Britney seemingly responded with one of her infamous dancing videos — this time to Billie Eilish‘s “bad guy” — with the caption “May the Lord wrap your mean ass up in joy today” (Jamie Lynn edited her own caption after, leaving only the emojis, while Britney also updated her own caption).
Jamie Lynn Denies Spending Time At A Condo Owned By Britney
From there, Jamie Lynn denied reports that she had spent time in a Florida condo owned by Britney. “I don’t own a condo and I can assure you that no one has ever bought me a place at the beach,” she defended, instead posting photos of herself and her family at at a Ritz-Carlton hotel in the same area. “Simple FACTS. Y’all need to stop reaching.”
Jamie Lynn later updated the caption to remove any reference to the condo headlines.
Britney Spears’ Feelings On A Relationship With Jamie Lynn Revealed
While the social media jabs have simmered between Britney and Jamie Lynn, sources have spilled about the pairs’ current relationship status to HollywoodLife EXCLUSIVELY. Britney “is not interested” in a relationship at this time, the insider spilled.
Britney< would eventually like to have a good relationship with her sister, but it’s hard because her sister is close to her mom and talks to her dad,” they explained. “It’s hard to get back to family dynamics when this isn’t cleaned up.”