Jamie Lynn Spears, sister to the "Toxic" singer, Britney Spears, rose to the limelight when she landed the role of "Zoey Brooks" from Nickelodeon’s hit show, "Zoey 101," in 2004.
Since 2002, the two could be seen attending events together as Britney’s musical career progressed throughout the years. She stated in a 2016 interview with WFAA, "[t]ruthfully, my childhood was so fun. Everything was new and everything was like Christmas because we were just from this small town and my sister had amazing success. It was so amazing to see my sister reach such heights."
Nickelodeon’s "Zoey 101" was one of the highest-ranked shows in the 2000s and had wrapped up its final season before Jamie Lynn in 2007 revealed that she and her then-boyfriend and later-to-be fiancé, Casey Aldridge, were expecting their first child, causing speculation that the show had been cancelled due to her pregnancy.
After the show’s final season, Jamie Lynn—who didn’t know that she was yet pregnant—auditioned at the age of 16 for the role of Bella Swan in "Twilight" but Kristen Stewart was casted instead.
With concerns about the paparazzi following Spears’ every move during her pregnancy, she and her fiancé, Casey, moved to Liberty, Mississippi in an attempt to avoid tabloid coverage of her pregnancy, but was unsuccessful in doing so. Spears and her family filed a complaint against paparazzo Edwin Merrino for allegedly stalking Spears and her family, but he was released later that day after posting bond.
In June 19, 2008, Jamie Lynn gave birth to her daughter, Maddie, at the age of 17, then left the public eye until 2013. She and her fiancé called off their engagement in March 2009, prompting her to move out in later in December. The two mended their relationship in August 2010, only for it to end four months later in November.
Five years after the birth of her child, Jamie Lynn and her sister, Britney, collaborated on "Chillin’ with You" from Britney’s 2013 album, "Britney Jean." She went onto Twitter to show her excitement for the collaboration that she says that she’s been working on during her five-year hiatus.
In 2014, one year after Jamie Lynn’s appearance on Britney’s album, she and her new fiancé, Jamie Watson, tied the knot in March; Spears has her second child, Ivey Joan Watson, in 2018.
Later in May of 2014 after her marriage, Spears released her only album to date, "The Journey."
In 2019, as revelations of Britney’s mental health treatment arose, it was revealed that Jamie Lynn was named as the trustee in Britney’s SJB Revocable Trust in 2020, which was amended by Britney’s then-co-conservators in 2018, according to legal documents.
In Britney’s 2021 court appearance, Jamie Lynn expressed support for her sister, along with Jamie Lynn’s husband who told the New York Post: "I can assure you her family loves her and wants the best for her. I wouldn’t be around people who weren’t. Who wouldn’t want to be in support of Britney?"