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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.Kristofferson composed his own songs and collaborated with Nashville songwriters such as Shel Silverstein.

Weeks later Kristofferson landed a helicopter in Cash's front yard, gaining his full attention.

[Note: In a later interview, Kristofferson maintained Cash was not at home when he landed the helicopter.

This is the only time an individual received the same award from these two organizations in the same year for different songs.

In 1971, Janis Joplin, who dated Kristofferson for some time until her death, had a number one hit with "Me and Bobby Mc Gee" from her posthumous album Pearl.

Then I'd go back to Nashville at the end of the week and spend a week up there trying to pitch the songs, then come back down and write songs for another week ...

I can remember "Help Me Make It Through the Night" I wrote sitting on top of an oil platform.Kristofferson recalled of his days as a pilot, "That was about the last three years before I started performing, before people started cutting my songs ...I would work a week down here [in south Louisiana] for PHI, sitting on an oil platform and flying helicopters.Sales were poor, although this debut album would become a success the following year when it was re-released under the title Me & Bobby Mc Gee.Kristofferson's compositions were still in high demand.At Oxford, he was also acquainted with fellow Rhodes scholar, art critic, and poet Michael Fried.

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