Kris Kristofferson: Five (or maybe 10) of his best songs

One of Kristofferson’s most enduring songs, Me and Bobby McGee, external, started out as a songwriting challenge.

Monument Records founder Foster had a crush on his secretary, Barbara “Bobbie” McKee, and wanted a song that would impress her.

Kristofferson accepted the assignment – but finding inspiration took time.

“I avoided him [Foster] for three or four months because there were only thoughts running through my head,” he said in 1973.

“I was driving back to New Orleans one night, the windshield wipers were going, and it started falling together.”

He based the song on the last scene of the Fellini film La Strada (The Road), in which a broken, inebriated man stares at the sea in despair at what his life has become, and the love he has lost.

Kristofferson turned that tale into the story of two drifters, who find love on the road and are separated, eventually, by death.

It contains one of his greatest lyrics: “Freedom’s just another word for nothin’ left to lose / Nothin’ ain’t worth nothin’ – but it’s free.”

Originally recorded by Roger Miller, it became a number-one hit for Janis Joplin, who recorded it weeks before her death in 1970.