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1990s

Jamie Lynn Spears

Showbiz Blood

The Spears women – mother Lynne, aspiring performer Britney and baby sister Jamie Lynn (left) – move to New York so Britney can get closer to the casting action. Lynne's husband, Jamie, a building contractor, and her eldest child, Bryan, stay behind in their native Kentwood, La. After landing in an Off-Broadway play, Britney decides she wants to go back home. Shortly after their return, the elder Spears sister gets cast in The New Mickey Mouse Club, where she performs with future boyfriend Justin Timberlake.

1998

Jamie Lynn Spears

November

Big Sis Brit Undresses

Britney's debut music video, "...Baby One More Time," causes a media firestorm for its sexual nature – the 17-year-old budding pop star is outfitted in a schoolgirl's uniform, revealing her midriff. Although she becomes pop's favorite Lolita, Britney (inset) is a down-home girl, who loves her seven-year-old baby sister (right, pictured with Lynne). "I like to take care of her. She's really, really sweet," Britney tells the Orlando Sentinel. "One time she had my CD in her stereo and was just singing away. She doesn't know any of the words – was just making them up."

2002

Jamie Lynn Spears

Jamie Lynn's All That

Jamie Lynn joins Nickelodeon in the kid network's sketch series, All That (pictured in a scene with her sister's boyfriend Justin Timberlake). "Of course I'm biased, but I definitely think Jamie Lynn has that 'It' quality," Britney tells USA Today. "She shines, and I'm proud of her." But Lynne gives her a relatively normal upbringing, keeping her in school at Kentwood's private Park Lane Academy and letting her shoot with Nickelodeon during her summer breaks.

Jamie Lynn Spears

August

A Spears Sister Act

At the 2002 Teen Choice Awards, Jamie Lynn, who has developed a tween following, makes an appearance with Britney. "She's the little star at school right now," Britney tells PEOPLE. "She's just 'Miss Everything' and lovin' every minute of it." But Jamie Lynn makes sure she's not just seen as Brit's little sister: "I'm me, she's her, let's get over it," she tells USA Today. "But it doesn't bother me, because I'm not here to be a huge person. It's not about proving to people how famous I am."

2005

Jamie Lynn Spears

January 09

Nick Springboard: Zoey 101

Jamie Lynn, 13, is given her own Nickelodeon series, Zoey 101 (pictured with costar Alexa Nikolas). She plays Zoey Brooks, a student at a newly coed boarding school. The series eventually becomes the second highest-rated show with tweens, just behind American Idol, and Jamie Lynn wins a Kids' Choice Award for Favorite Teen Actress. Dan Schneider, who created the show for Jamie Lynn, credits her appeal to her not realizing she's beautiful, famous and talented. "The net result is you have this real girl talking to you, sort of like the girl next door," he tells the AP.

2007

Jamie Lynn Spears

June

Separating from Britney

On the set of Jamie Lynn's Zoey 101, Britney hands her mother a letter that asks Lynne to stay away from her two sons with ex-husband Kevin Federline. Jamie Lynn, who lives with Lynne, is caught in the middle of the rift between her mother and sister, according to a family friend. The falling out stems from the family's involvement with Britney's rocky stint in rehab last February, after she exhibited bizarre behavior, including shaving her head.

Jamie Lynn Spears

October

Jamie Lynn Defends Britney

With a custody battle raging between Britney and Federline, the Spears women finally reunite. "Poor Jamie Lynn had to balance those two sides, her mom and her sister," a source tells PEOPLE. Days later, Jamie Lynn jumps to Britney's defense when a woman yells for Britney to move out of the neighborhood. Jamie Lynn gets between the woman and her sister, yelling a few choice words of her own (left).

Jamie Lynn Spears

December 18

Jamie Lynn Pregnant at 16

Jamie Lynn announces she's 12 weeks pregnant on the cover of OK!. "I was in complete and total shock and so was he," the teen star says of her pregnancy with boyfriend (right) Casey Aldridge's baby. Her mother Lynne adds, "I didn't believe it because Jamie Lynn's always been so conscientious...I mean, this is my 16-year-old baby." Her pregnancy also raises questions about her future with Nickelodeon.

2008

Jamie Lynn Spears

March-June

Jaime Lynn Gets Engaged & Has Baby

Days before her 17th birthday, Jaime Lynn sports a diamond ring from 18-year-old Aldridge. The newly engaged mom-to-be also buys a home in Louisiana. On June 19, with Aldridge, Britney, her parents and brother Bryan at her side, she welcomes daughter Maddie Briann.

2010

Jamie Lynn Spears

Moving Out and On

Jamie Lynn splits with boyfriend Casey Aldridge and moves out of their Liberty, Miss., house, with their 19-month-old daughter, Maddie. "She did a lot of growing up but he didn't," a source tells PEOPLE. "I think she put up with more than she cared to put up with." The 18-year-old single mom also finds a new man, businessman James Watson, 28.

Photo Credits

BIOGRAPHY (top to bottom): Splash News Online; Jill Johnson/JPI, inset: INF; Lisa Rose/JPI; Lucy Nicholson/AP; Mike Rozman/FIlmmagic; Splash News Online, inset: Bauer Griffin; JFX; Alex Berliner/Berliner; X17; Winslow/Graeme/Splash News Online

Edited by Julia Wang

Jamie Lynn Spears

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