Leland was born in Lubbock, Texas, but his father's military career moved his family to Japan when he was five years old. Later, the family moved to Plano during his sophomore year in high school. While in Plano, Leland played football for Plano High School. He sustained a serious knee injury the year the Wildcats won the 1971 AAA State Championship. This injury forced him to leave behind athletics and transition into theater.
In 1980, Leland graduated from Texas Tech University with a bachelor's degree in acting and directing.
Leland first appeared onstage at Disneyland at 6 years old in a Wild West show. That began his dream of being an entertainer. After graduating from college, Leland moved to Dallas where he worked in local theatre and found an agent. He also got a part in one episode of the TV series Dallas and in an episode of In the Heat of the Night. He later appeared in seven episodes of the TV series Walker, Texas Ranger, in the 2003 Texas Chain Saw Massacre remake, and as an executive in the film Hancock. His most visible roles, though, remain those of football booster John Aubrey in the film Friday Night Lights and of the similar character, Buddy Garrity, in the TV series of the same name.

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