Reese Witherspoon became America's bubbliest sweetheart when she took her breakout role in 2001's Legally Blonde. Five years later, Reese showed the world a different side of her when she played June Carter in Walk the Line, a role which earned her the Oscar that year for best actress. Unfortunately, not long after her career breakthrough Reese's eight-year marriage to Cruel Intentions co-star Ryan Phillipe fell apart. The couple has two daughters together, Ava Elizabeth and Deacon. After Ryan, Reese went on to date Jake Gyllenhaal for two years before marrying Jim Toth in 2011.