About the Song Kris Kristofferson, the quintessential outlaw country singer-songwriter, has always been a master storyteller. His songs are often character sketches, painting vivid portraits of flawed, complex individuals navigating life’s trials and tribulations. “The Pilgrim, Chapter 33,” from his 1971 album “The Silver Tongued Devil and I,” is a prime example of this. More … Continue reading The Pilgrim’s Progress: Deconstructing Kris Kristofferson’s “The Pilgrim, Chapter 33”