I saw this video posted about how he wrote "Why Me" and I looked up a bit more on him.
Apparently he was Army. Not only army, but a helicopter pilot and a ranger. Hmm:
Kristofferson, under pressure from his family, ultimately joined the U.S. Army and attained the rank of
Captain. He became a helicopter pilot after receiving flight training at
Fort Rucker,
Alabama. He also completed
Ranger School. During the early 1960s, he was stationed in
West Germany as a member of the
8th Infantry Division.
[13] During this time, he resumed his music career and formed a band. In 1965, when his tour of duty ended, Kristofferson was given an assignment to teach English literature at
West Point.
[14] Instead, he decided to leave the Army and pursue songwriting. His family disowned him because of this decision and they never reconciled with him.
[15] They saw it as a rejection of everything they stood for, in spite of the fact that Kristofferson has said he is proud of his time in the military, and received the
American Veterans Awards "Veteran of the Year Award" in 2003.
[16][17] Some of these old school artists led pretty interesting lives.