Our other similarities were that neither of us could sing or play guitar very well, but it never stopped him from becoming a country music legend.
He died on Sunday at 88 — and it’s hard to tell if The Boss wouldn’t prefer him back and me gone, such is the degree of maudlin around here, with endless replays of dusty vinyl records, CDs and YouTube videos.
The Boss says Kristofferson was rightly described as “the poet laureate of longing and loneliness”. The classics he crafted illuminated the careers of countless artists — all of whom made his songs their own.
Kris had grown up in an army family, studied literature and earned a Rhodes Scholarship to Oxford, where he read the Romantic poets such as Blake and Keats. He then trained as a helicopter pilot in the army and was posted to Germany, but abandoned the army life to try his luck writing songs in Nashville — seemingly a risky move.
While cleaning ashtrays in bars he learned to make his songs less formal and sound more like people talk. First came For The Good Times, a pop hit for Ray Price in 1970. Next, Sunday Morning Coming Down became a No.1 country hit for his mentor, Johnny Cash, who burnished the opening couplet with his gravelly mournfulness:
Well, I woke up Sunday morning
With no way to hold my head that didn’t hurt
And the beer I had for breakfast wasn’t bad
So I had one more for dessert…
It turns into a bleakly powerful song of lost childhood and desolation, and Kristofferson’s knack for poetic images continued unabated with Me and Bobby McGee, where Janis Joplin (with whom he had a brief affair) sang the definitive version: “Freedom’s just another word for nothing left to lose/Nothin’ ain’t worth nothin’ but it’s free..”
It was Joplin’s last album, recorded a few days before her death from an overdose, and Kris told an interviewer 35 years later he still hadn’t got over the intense emotion in her recording of the song.
Later that year Help Me Make It Through The Night became a No.1 country and Top 10 pop hit for Sammi Smith, and legions of country stars such as Willie Nelson, Waylon Jennings and Roger Miller were now recording his songs. His own raspy voice and out-of-pitch vocals never had the same broad appeal — but he produced 18 studio albums all the same.
He had a long screen career from the early 1970s, appearing as the famed outlaw in Peckinpah’s Pat Garrett and Billy the Kid, then with Ellen Burstyn in Alice Doesn’t Live Here Anymore and later with Barbra Streisand in A Star Is Born. He starred in over 50 movies.
But he came back to country music in the mid-1980s with The Highwaymen — joining Johnny Cash, Waylon Jennings and Willie Nelson — and wrote more fine songs.
The Boss went to see Kris at his last appearance at Hamer Hall in late 2019; he stopped touring soon after but made a final stage appearance a little more than a year ago, in April, 2023, for Willie’s 90th birthday celebration. He took the stage with Rosanne Cash to sing his Loving Her Was Easier (Than Anything I’ll Ever Do Again).
Another evocative lyric, with William Blake whispering in the background. Woof!
