A Southern debutante with a penchant for Container Stores, Tupperware and organization (so much so that the name of her production company is Type A which was also her childhood nickname), Reese Witherspoon broke into modeling and commercials around 7 and made her film debut in “The Man In The Moon” at 14. Before completing high school, she’d moved on to lead roles in films like “Jack The Bear” and “A Far Off Place.” She started an intense and quick love affair with Ryan Phillippe at her 21st birthday party. They moved in together mere months after meeting, costarred in 1999’s “Cruel Intentions” and were married later that year when she was six-months pregnant. Daughter Ava was born in September 1999 and brother Deacon followed in 2003. Meanwhile, Witherspoon catapulted herself to the A list by earning critical kudos and a mainstream fanbase with “Election,” “Legally Blonde,” “Sweet Home Alabama” and “Walk The Line.” Playing June Carter Cash in the latter nabbed a Golden Globe and an Oscar in 2006, which unfortunately was the same year she split from Phillippe. She picked up the pieces with her “Rendition” costar Jake Gyllenhaal, but it was ultimately agent Jim Toth who convinced her to take a second walk down the aisle in 2011. They welcomed son Tennessee in September 2012. Her America’s sweetheart reputation took a hit in April 2013 when she was arrested in Atlanta for disorderly contact after Toth was pulled over for a suspected DUI.