The five best movies with Reese Witherspoon are mostly fun-loving, light-hearted movies. Don't stereotype her because of that though. She is a great actress in all genres of films, including thrillers and drama.

  1. "Walk the Line." This film with Witherspoon is based on the life of Johnny Cash. More specifically, it is the story of his relationship with June Carter, played by Witherspoon. It reveals how they met, the struggles they went through in their relationship and Cash's battle with drugs.

  2. "Legally Blonde." Reese Witherspoon plays a sorority girl in this comedy about a blonde student who is attempting to win back her boyfriend. To get his attention and prove that she is not stupid, she attends Harvard to get a law degree. Her old boyfriend's new girlfriend doesn't like the idea and tries to throw a wrench in it.

  3. "Cruel Intentions." In this movie with Reese Witherspoon, her character is the virgin daughter of the school headmaster. Sarah Michelle Gellar and Ryan Phillippe, the two main characters, have a bet surrounding Reese's character.

  4. "Pleasantville." Jennifer (Reese Witherspoon) and her brother are mysteriously transported back into the 1950s. They find themselves to be in a sitcom. However, Jennifer is not exactly 'pure as the driven snow,' and this causes problems in the sitcom's town of Pleasantville.

  5. "Election." Made in 1999, this is widely named as one of the best movies with Reese Witherspoon. She is running in an election to be student body president, but one of the teachers does not believe she deserves it. The story unfolds as he tries to thwart her plans.