Witherspoon landed her first feature role as the female lead in the movie The Man in the Moon in 1991; later that year she made her television acting debut, in the cable movie Wildflower. In 1996, Witherspoon's performance in Freeway established her as a rising star and led to roles in three major 1998 movies: Overnight Delivery, Pleasantville, and Twilight.
Witherspoon married actor and Cruel Intentions co-star Ryan Phillippe in 1999; they have two children, Ava and Deacon. The couple separated at the end of 2006 and divorced in October 2007. Witherspoon owns a production company named Type A Films.