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After a lengthy period of struggle, Kris Kristofferson achieved remarkable success as a country songwriter at the start of the 1970s. His songs "Me and Bobby McGee," "Help Me Make It Through the Night," "Sunday Mornin' Comin' Down," and "For the Good Times," all chart-topping hits, helped redefine country songwriting, making it more personal and serious, much in the way that Bob Dylan's songs had transformed pop music songwriting in the mid-'60s. By 1987, it was estimated that Kristofferson's compositions had been recorded by more than 450 artists. His renown as a songwriter enabled him to launch a moderately successful career as a musical performer and that, in turn, brought him to the attention of Hollywood, leading to a lengthy career as a film actor.
The eldest of three children of an Air Force major general who retired from the military to head up air operations for the Saudi Arabian company Aramco, Kristofferson spent most of his childhood in Brownsville, TX, though his family moved around, finally settling in San Mateo, CA, by his junior high-school years. He graduated from San Mateo High School in 1954 and entered Pomona College in Claremont, CA. There he studied creative writing and he won first prize and three other placements in a collegiate short-story contest sponsored by Atlantic Monthly magazine. He graduated Phi Beta Kappa in 1958, having secured a prestigious Rhodes scholarship to continue his studies at Oxford University in England. While at Oxford, he wrote and performed his own songs, which brought him to the attention of manager Larry Parnes (who handled Tommy Steele and other British pop stars). Signing with Parnes, he made recordings for Top Rank Records produced by Tony Hatch (apparently never released) and performed under the name Kris Carson, but he was not successful.
After earning a master's degree in English literature from Oxford in 1960, Kristofferson intended to continue his studies there. But during a Christmas break back home in California, he resumed his relationship with an old girlfriend, Fran Beir, and they married. Instead of returning to Oxford, he joined the Army. Like his father, he became a pilot, learning to fly helicopters. He was assigned to West Germany and went there with his wife and their daughter. During the early '60s, while rising to the rank of captain, he eventually returned to writing and performing, organizing a soldiers' band to play at service clubs. Hearing his songs, a friend suggested sending them to a relative of his, the Nashville songwriter Marijohn Wilkin. Kristofferson did so and he received encouragement from Wilkin, who had become a music publisher by founding Bighorn Music. In 1965, Kristofferson was reassigned to the West Point military academy, where he was to become an English instructor. He spent a two-week leave in June 1965 in Nashville, where he looked up Wilkin and decided to try to become a country songwriter instead. He resigned his commission and moved his family to Nashville, signing to Bighorn, which gave him a small weekly stipend that he augmented with a variety of jobs, including janitorial work, bartending, and flying helicopters to and from offshore oil rigs in the Gulf of Mexico. He and his wife had a son who was born with a defective esophagus, resulting in thousands of dollars in medical bills. Eventually, the couple divorced.
Kristofferson scored his first success as a songwriter with "Viet Nam Blues," which was recorded by Dave Dudley and peaked in the country Top 20 in April 1966. As a recording artist, Kristofferson was signed to Epic Records and released a lone single, "Golden Idol"/"Killing Time," in 1967, but it missed the charts. (He later re-recorded both songs for his Surreal Thing album.) Roy Drusky recorded Kristofferson's "Jody and the Kid" and took it into the country Top 40 in the summer of 1968 and Billy Walker and the Tennessee Walkers' version of his "From the Bottle to the Bottom" peaked in the Top 20 of the country charts in April 1969. But by that spring, those three chart placings and his failed single were all Kristofferson had to show for almost four years of effort in Nashville. He had moved to Fred Foster's Columbine Music and begun to collaborate occasionally with Foster, and he got a break when Roger Miller decided to record one of their songs, "Me and Bobby McGee," a ballad about hoboing that recalled earlier Miller hits like "King of the Road," but with more of a hippie slant. Miller ended up recording not only "Me and Bobby McGee," but also two other Kristofferson compositions, "Best of All Possible Worlds" and "Darby's Castle," for his August 1969 album, Roger Miller. "Me and Bobby McGee" was released as a single in advance of the album and it peaked in the country Top 20. Meanwhile, Kristofferson had begun to gain recognition as a performer, thanks to Johnny Cash, who introduced him at the Newport Folk Festival that summer and featured him on his network television show.