Jamie Lynn Spears

Jamie Lynn Spears grew up in the spotlight, and was already a star with a slightly checkered past at the ripe old age of 22 when she launched a new career as a country singer. The younger sister of pop icon Britney Spears, Jamie Lynn Spears was born in McComb, Mississippi on April 4, 1991. While Britney was scoring a record deal and becoming a major star in the late '90s, Jamie Lynn was attending a private Christian school, where she was a cheerleader and played on the basketball team. That would change: in 2002, when Jamie Lynn was 11, she made her professional acting debut in the movie Crossroads, playing a younger version of her sister Britney's character, Lucy Wagner. Jamie Lynn showed a knack for acting, and that same year she became a regular on the children's TV comedy series All That. Nickelodeon, the cable network that aired All That, was impressed enough with Spears that they cast her in the lead of her own series, Zoey 101, in which she played Zoey Brooks, one of the first female students at a traditionally all-boys private school. Debuting in early 2005, with young Spears singing the theme song, Zoey 101 was a success in the ratings, and ran for four seasons and 65 episodes.

However, in December 2007, shortly after Spears finished taping the final episodes of Zoey 101, she made a startling announcement: 16-year-old Jamie Lynn was pregnant, and her boyfriend of two years, 18-year-old Casey Aldridge, was the father. Spears and Aldridge made plans to marry, and she gave birth to a daughter, Maddie Briann Aldridge, in June 2008. However, the on-and-off relationship between Spears and Aldridge finally came to an end in 2010, and she relocated to Nashville, Tennessee, with an eye toward becoming a country music artist. In November 2013, Spears released her first digital single, a tune she co-wrote with Rivers Rutherford called "How Could I Want More." The song earned positive reviews from the country music press, revealing a sound and style that was mature beyond Spears' 22 years, and it rose to 29 on Billboard's Hot Country Singles chart. Spears announced plans for a full-length album to be released in 2014, and she made a guest appearance on Britney Spears' 2013 album Britney Jean, duetting with her sister on "Chillin' with You."