Jamie Lynn and Britney Spears timeline – What to know about their relationship

BRITNEY Spears sparked questions about her sisters connection to her conservatorship saying that she wants to her sue her family saying "My whole family did nothing.”

But Britney and Jamie Lynn Spears have always shared a very close bond and despite their ten year age difference Jamie Lynn has been said to be very protective of her pop-star older sister.

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Here's a timeline of Britney and Jamie Lynn's relationship:

2002

Jamie Lynn first appeared as the younger version of Britney Spears’ character in the 2002 movie Crossroads. 

"I love my little sister and I am overprotective with her, and I don't mind saying that," Britney told Real Access after the 2002 film came out.

"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."

2003

Since the beginning of Britney's career, the sisters where often together and attending premieres and other fun events together.

2004

Britney gushed about how proud she was of her little sister when it was announced that she would be starring in her own TV show Zoey 101.

"Jamie Lynn is turning into such a beautiful little lady. Her new show is coming out soon and I am sooo proud of her,"

2005

Zoey 101 premiered on Nickelodeon with Jamie Lynn singing the theme song, Follow Me.

But Jamie Lynn and co-star Alexa Nikolas were often feuding on set forcing big sister Britney to step in.

Several outlets at the time reported that Britney “proceeded to scream that Alexa was an ‘evil little girl,’ and that she had better watch herself or she ‘will never work in this town again!”‘

2006

Britney gave birth to her second son Jayden James Federline. Jamie Lynn was excited to be an aunt to two little boys.

2007

Jamie Lynn Spears announced that she was pregnant at 16 years old the same year that Britney lost custody of her children.

That year, Britney notoriously had a mental break down and shaved her head.

2008

Zoey 101 aired its last episode on Nickelodeon as Jamie Lynn moved back down South, got her GED in February 2008 and prepared for the birth of her first child.

Her daughter Maddie Aldridge was born on June 19, 2008, in Mississippi where both Britney and Jamie Lynn were born.

Britney recounted, "That was special, but it was also strange because [Jamie Lynn's] always been the baby, and now the baby was having a baby."

"It was mind-boggling. I was shocked a little bit. But it was really cool, and she was happy. When she got to the hospital, we all thought it was going to be an all-day thing, and instead, the baby just sort of popped out. 'OK, we're happy now!'"

2009

Jamie Lynn was planning to marry her hometown boyfriend and father to her child.

The teen mother asked Britney to be a bridesmaid in her upcoming wedding.

2010

Britney and Jamie Lynn were both engaged as the time and reportedly joked about having a double wedding.

2011

Jamie Lynn made her musical debut in Nashville and although big sister Britney wasn't there to see it she offered her congrats on Twitter.

"@britneyspears thanks- just wish you and J were there!! love yall!" Jamie Lynn tweeted back to her big sis.

2012

Just like the Spears sisters, the Spears cousins have grown up to be very close despite living across the country from each other.

Jamie Lynn shared, "For now, Maddie's biggest concern in life is when she gets to see her cousins next. She's always asking, 'Why can't we have Preston and JJ here?' They're very close. They're like brothers and sister. They're so stinking cute."

"And Maddie loves her Aunt Britney's songs," the young mom added. "She just loves the whole dress-up thing that goes with it. She loves dancing and singing and all of that. I definitely think music is in her genes."

2013

Jamie Lynn decided to get a boost in her music career, teaming up with her international pop-star sister.

The two sang together on Chillin' With You, on Britney's 2013 album Britney Jean.

2014

Jamie Lynn gets married to Jamie Watson and released her debut EP country album, The Journey.

"For me and my sister the relationship [has] always been a really special one. I'm proud of my sister."

"She went after her dream from a small town and she's still doing what she loves, so there's something to be said about that and something to be really proud of. So I definitely look at that as, you know, it gives me motivation and really inspires me to keep going."

"There's such a big age difference between me and my sister that I think [she] almost was like a second mom," she continued of Britney. "She's so supportive and she's so encouraging of me and she's like my biggest fan…She's always had my back."

2015

Jamie Lynn has continuously spoken openly up about how Britney inspires her.

“I take a lot away from [Britney’s]… drive,” Jamie Lynn said. “Seeing someone who’s worked to create the kind of life they want from a simple passion.” 

2016

When Jamie Lynn made her Grand Ole Opry debut in Nashville, Britney and their brother, Bryan Spears, introduced her performance in a surprise appearance.

"Thanks to the Opry for letting me introduce this beautiful, young lady who is my heart and my soul," Britney said. "Not only is she beautiful and extremely talented, she's my little sister…Jamie Lynn Spears!"

2017

Jamie Lynn shared the news of her second pregnancy on Twitter where Britney congratulated her.

Britney wrote on Twitter: “Maddie is going to be the best big sister!!! So happy for you @jamielynnspears!!!! Love you all sooo much!!!”

2018

Jamie Lynn was named the trustee of Britney’s $8 million estate by Jamie and Britney’s lawyer, Andrew Walletin in August 2020.

Jamie is the “sole beneficiary” of the SJB Trust, which Britney created in 2004 to protect her sons Sean Preston and Jayden James’ financial future and her fortune.

Due to this, when Britney dies, Jamie Lynn will receive “the entire principal of the Trust, including all accused and undistributed and unrealized income.”

Meaning Jamie Lynn will inherit Britney’s fortune, not her sons.

2019

"10 years ago, who was there?? I have been here long before anyone else, and I'll be here long after," Jamie Lynn wrote on Instagram.

"I love my sister with everything I have. So, anyone or anything that speaks to the contrary can GTFOH with all the comments about what you don't understand. Do not come for me or the ones I love anymore. You can move the 'blank' outta here with all that, just like this other lady who was running her mouth."

Jamie Lynn replied to Instagram comments saying, "Haha nice try, but I have NEVER been paid a dime from my sister, that is HER hard earned money, and I am NOT entitled to a cent of it," Jamie Lynn replied.

"I would not spend money I did not earn."

Another time she took to the comments saying that Britney "is a strong, badass, unstoppable woman, and that's the only thing that is OBVIOUS." (These posts were later deleted.) 

2020

Jamie Lynn Spears again came at Instagram critics who claimed that she was purposely not speaking out regarding her sister, Britney Spears, and her rumored mental health struggles.

"If you deal with mental illness or care for someone dealing with mental illness, then you know how important it is to respect the situation with privacy for the person, and the family trying to protect their loved ones, no matter how it may appear to the public, and as the public we must learn to do the same," Jaymie Lynn wrote on Instagram.

"I pray this doesn't bring shame to anyone dealing with mental illness, you are not alone, and you are loved."

When the Britney Army came for Jamie Lynn again she replied, "You have no right to assume anything about my sister, and I have NO right to speak about HER health and personal matters. She is a strong, badass, unstoppable woman, and that's the only thing that is OBVIOUS."

She later echoed a similar sentiment, "I would never speak out just to clarify things to the public, when the person it pertains to does not want that to happen," wrote Jamie Lynn. "I'd rather take all the hate, then speak about someone elses personal matter, that they want to keep private."

2021

Britney included a picture of her sister along with photos of Sharon Stone, Natalie Portman, Miley and Noah Cyrus, Sarah Jessica Parker and fitness teacher Tawny Janae in a March 24 Instagram post captioned,

"These are the women that have truly inspired my life!!!! Being away from family and my boyfriend while quarantining was really hard for me but the good thing about social media is we can connect in a different way that helps us feel not alone in this crazy world!!! These cool ladies always add a spark to my day!!!!"

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