PurpleheartOklahoma (scroll down)

This will surprise you 
Many people may not know about his time in the U.S.Army. He is the son of an Air Force General and a accomplished Golden Gloves boxer. He graduated from Pomona College with a B.S. degree and then became a Rhodes Scholar from Oxford University.
He joined the U.S. Army at the prompting of his father. After graduating from Officer Candidate School he attended and graduated from both Army Airborne and Ranger training in the top of each class. He was selected for U. S. Army Special Forces Training but refused so that he could attend pilot training where he earned his wings and became an accomplished U.S. Army helicopter (gun ship) pilot, achieving the rank of Captain.
He was about to be promoted to the rank of Major and appointed to teach at West Point when he resigned his commission from the Army to go into music and acting. You can tell in this video that his time in the military means a lot to him.
 
http://www.youtube.com/v/PU-A7eqadho   or

Kristoffer Kristofferson was born in Brownsville, Texas, to Mary Ann (née Ashbrook) and Lars Henry Kristofferson, a U.S. Army Air Corps (later U.S. Air Force) Major General.[1] His paternal grandparents immigrated from Sweden, and Kristofferson's paternal grandfather was an officer in the Swedish Army. When Kristofferson was a child, his father pushed him toward a military career.[2] Like most "military brats", Kristofferson moved around frequently as a youth, finally settling down in San Mateo, California, where he graduated from San Mateo High School. An aspiring writer, Kristofferson enrolled in Pomona College in 1954. He experienced his first dose of fame when he appeared in Sports Illustrated's "Faces in the Crowd" for his achievements in collegiate rugby union, football, and track and field. He and fellow classmates revived the Claremont Colleges Rugby Club in 1958, which has remained a Southern California rugby dynasty.[clarification needed] Kristofferson became a member of Kappa Delta at Pomona College, graduating in 1958 with a BA, summa cum laude in Literature. In a 2004 interview with Pomona College Magazine Kristofferson mentioned philosophy professor Frederick Sontag as an important influence in his life.[3]

Kristofferson earned a Rhodes Scholarship to the University of Oxford, where his college was Merton. While at Oxford he was awarded his blue for boxing and began writing songs. With the help of his manager, Larry Parnes, he recorded for Top Rank Records under the name Kris Carson. Parnes was working to sell Kris as "a Yank at Oxford" to the British public; Kristofferson was willing to accept that promotional approach if it helped his singing career, which he hoped would enable him to progress towards his goal of becoming a novelist.[4] This early phase of his music career was unsuccessful.[5]

In 1960, Kristofferson graduated with a BPhil in English literature and married an old girlfriend, Fran Beer. Kristofferson, under pressure from his family, ultimately joined the U.S. Army and achieved 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.[6] It was during this time that he resumed his music career and formed a band. In 1965, when his tour of duty ended, Kristofferson was offered a position as a professor of English Literature at West Point.[7] Instead, he decided to leave the Army and pursue songwriting. His family disowned him because of this decision and 

they never reconciled with him. They saw it as a rejection of everything they stood for while Kristofferson has stated that he was greatly influenced by the poet William Blake while at Oxford, who had proclaimed that if one has a God-given creative talent then one should use it, or else reap sorrow and despair. Kristofferson sent some of his compositions to a friend's relative, Marijohn Wilkin, a successful Nashville, Tennessee, songwriter but when he arrived in the town to see Sam Phillips of Sun Records his shoes were, according to Philips 'falling off his feet.'