Desc: Waylon: An Intimate Portrait of an Outlaw: Directed by Larry Sands. With Richie Albright, Bobby Bare, Mark Chesnutt, Jessi Colter. When a country singer becomes a superstar and then that superstar becomes a legend, he leaves the boundaries of normal celebrity and lives in a place in the stars all his own. Waylon - An Intimate Portrait of an Outlaw is the documentary of Waylon Jennings, which is officially recognized by Jessi Colter and the Jennings family. The documentary follows the life of country music legend Waylon Jennings, and is a raw look into how the rise of a small town Texas dreamer became one of the most influential country music singers in the history of music. It tracks Waylon from his very poor beginnings in Littlefield, Texas growing up with his brothers; picking cotton and his guitar, to befriending and playing with Buddy Holly and his move to Phoenix that shot him to fame... You've heard of Waylon Jennings and how he changed country music. You've heard the stories of his life and travels, but you haven't heard them like this. His story is told by the people who knew him best and went along for the ride; his family and those he considered family.