The wholesome, 16-year-old little sister of Britney Spears left mouths agape in 2007 when she announced to OK! magazine that she was pregnant. At the time, Jamie Lynn Spears was starring in Nickelodeon's Zoey 101—and was marketed as a role model for teens. Whoops. The Nick series met its end in May 2008 and the starlet gave birth to daughter Maddie that June.