On a Sunday mornin' sidewalk/I'm wishin', Lord, that I was stoned/'Cause there's somethin' in a Sunday/That makes a body feel alone...

With songs such as "Sunday Mornin' Comin' Down," Kris Kristofferson expanded the vernacular of country music, bringing realism, gritty authenticity, and a literate sensibility - he was an Oxford-schooled Rhodes Scholar -  to a genre already known for its unvarnished musical stories of pain and heartbreak.  Kristofferson would find himself at the vanguard of the so-called outlaw country movement, but his songs and career far eclipsed that tag.  The singer-songwriter, who died on September 28 at the age of 88, starred onscreen opposite Barbra Streisand, duetted with Miss Piggy, and found his songs turned into hits by everybody from Johnny Cash to Perry Como.

Texas native Kristofferson moved to Nashville in 1965.  Initially, it was just a two-week leave from the U.S. Army.  A Captain in the Army having served as an Airborne Ranger helicopter pilot, he'd been assigned to West Point as an English teacher. But before accepting the commission, he had to follow his passion.  At the end of the leave, he resigned his commission and moved to Nashville full-time.

Eager to enter the music business, he worked in a variety of jobs including that of a janitor at Columbia Records' studio where he famously witnessed Bob Dylan creating the album that became Blonde on Blonde.  He placed the poignant "Sunday Mornin' Comin' Down" with Ray Stevens (a keen-eared singer-songwriter and musical satirist in his own right) before he got it to Johnny Cash.  The Man in Black's 1970 recording, helmed by Blonde on Blonde producer Bob Johnston, became a No. 1 Country hit; in Kristofferson's own estimation, he no longer had to work after its success.  But work, he did.

More songwriting credits came with his compositions being recorded by artists such as Jerry Lee Lewis, Roger Miller, and Faron Young.  He linked with Epic Records as a performing artist and released a single, but it did not chart.  Monument Records, run by publisher/impresario Fred Foster - signed him in 1970 to a recording contract.  Kristofferson's debut LP, Kristofferson, was released later that year.  It would not achieve any chart success until it was re-released under the title Me and Bobby McGee in 1971.  That was, of course, the Kristofferson song that went to the top of the charts in Kristofferson's onetime girlfriend Janis Joplin's version off her posthumous album Pearl.  By then, he'd added such instant standards to his songbook as "For the Good Times" and the Grammy-winning "Help Me Make It Through the Night."  These songs weren't only getting attention in country circles, but with such all-time pop stars as Perry Como, Andy Williams, Bobby Darin, and Johnny Mathis as well as soul artists like Joe Simon, Wilson Pickett, Percy Sledge, and Gladys Knight and the Pips.  Kristofferson bridged the gaps between traditional country and the counterculture, and between country and pop.

Kristofferson remained an in-demand songwriter throughout the 1970s even as he continued to record albums for Monument.  Although his songwriting success most often outweighed his recording success, he notched a No.1 Country hit in 1973 with "Why Me" off his album Jesus Was a Capricorn.  Between 1973 and 1978, he jointly released three albums with then-wife Rita Coolidge.  They won their first of two Grammy Awards for "From the Bottle to the Bottom" on 1973's Full Moon.

With his ruggedly handsome looks, it was unsurprising that Kristofferson found his way to Hollywood, beginning a long career there with 1971's Dennis Hopper film The Last Movie.  He portrayed Billy the Kid in Sam Peckinpah's Pat Garrett and Billy the Kid in 1973 and starred alongside Ellen Burstyn in Martin Scorsese's Alice Doesn't Live Here Anymore in 1974.  He won a Golden Globe for his role as John Norman Howard, perhaps his most indelible film part, opposite Barbra Streisand in 1976's electrifying A Star is Born.

Kristofferson continued to record for Monument with his last original album for the label, To the Bone, being released in 1981.  He would collaborate with Johnny Cash, Waylon Jennings, and Willie Nelson as The Highwaymen for the successful Highwayman album in 1985 and two follow-ups.  Kris signed with Mercury Records, where he would release two albums, one in 1986 and one in 1990. Later releases came on the Atlantic, New West, and KK labels.  His final studio album, The Cedar Creek Sessions, arrived in 2016 on KK Records.  In his later years, he saluted Joni Mitchell for her 75th birthday concert and joined Barbra Streisand onstage in London's Hyde Park.  He announced his retirement in early 2021.

A verse of Jimmy Webb's "Highwayman" goes, I fly a starship across the universe divide/And when I reach the other side, I'll find a place to rest my spirit if I can/Perhaps I may become a highwayman again/ Or I may simply be a single drop of rain/But I will remain/And I'll be back again/And again, and again, and again/And again, and again...

Of that, there's no doubt.  The timeless songs of Kris Kristofferson will be heard again and again and again and again...