Ron Livingston first came to the attention of film audiences in 1996, when he portrayed one of Jon Favreau's Rat Pack-obsessed cronies in Swingers. Over the next few years, the actor began taking more and more leading roles, earning recognition and making a name for himself in the process. A graduate of Yale, where he received a B.A. in Theatre Studies and English Literature, Livingston began acting at the Williamstown Theatre Festival while in college. After graduation, he headed to Chicago, where he performed at the Goodman Theatre. Livingston made his film debut in the 1992 Dolly Parton comedy Straight Talk, and the following year he had a supporting role in the independent film Some Folks Call It a Sling Blade.
After catching the eyes of audiences in the cult-hit Swingers, Livingston began to take on increasingly more prominent film roles. In 1999 he could be seen in no less than three films, beginning with the comedy Office Space, in which he had the starring role. While the film performed theatrically, it slowly gained an audience on home-video and was later regarded as a modern comedy classic.