Leland was born in Lubbock, Texas, but 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.
In 1980, Leland graduated from Texas Tech with a bachelor’s degree in acting and directing.
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 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, are that of football booster John Aubrey in the film Friday Night Lights and the similar character, Buddy Garrity, in the TV series of the same name.