In Nashville, Reese attended the exclusive school Harpeth Hall and eventually attended Stanford where she majored in English literature. Along the way, she performed in local commercials and some modeling but not at all in acting until Reese and some of her friends attended an open audition for movie extras.

This first attempt overwhelmed director Robert Mulligan piloting her for a leading role and her feature debut in the 1991 drama "The Man in the Moon" opposite Sam Waterston. Reese casted the challenging role of a young girl in 1950's Louisiana who, for the first time, falls in love. With the success of the drama and her good portrayal of her role, Reese instantly leaped to an astronomical audience acceptance.

Follow through of her initial success landed on various TV roles. In 1991, she played a role as a Depression-Age girl whose empathy and encouragement transformed the life of an epileptic child who has been ill-treated by her family in the TV movie "Wildflower." Afterwards, she was cast in "Desperate Choices: To Save My Child." This is still followed by another TV movie, which also marked her last, the CBS mini-series "Return to Lonesome Dove."

But the big year is yet to come. In 1998, Reese performed alongside some real filmic giants Paul Newman, Gene Hackman and Susan Sarandon in “Twilight.” Getting more experienced, she also played roles in the critical hit “Pleasantville,” the mainstream hit “Cruel Intentions,” “Election” (her first movie playing the central character which earned her the Best Actress Award in the 1999 National Society of Film Critics), gritty fun “Best Laid Plans,” the extremely funny and feminist movie “American Psycho,” the big-hit movie “Legally Blonde” which also earned her a second Golden Globe nomination and the $100 million hit “Sweet Home Alabama.”

Reese is married to Ryan Phillippe on June 5th, 1999, in South Carolina at the Wide Awake Plantation and on September 9th, 1999, Reese gave birth to their daughter, Ava Elizabeth.

In her mid-twenties, Reese was able to set up her production company Little Miss Type A (with Debra Siegal and a deal signed with Universal). She also managed to helped underprivileged people back in Nashville through scholarships.