Prine took ill on March 27 with what was described in a statement from his family as a «sudden onset» of the illness, and was intubated two days later.

His wife Fiona, who tested positive on March 18 and has since recovered, updated fans on the singer’s battle with the coronavirus and asked them to pray for him. She said in an update last week on social media that the musician had developed pneumonia after being admitted to hospital in Nashville.

Prine in January was honoured with a lifetime achievement Grammy, and in 2019 was inducted into the Songwriters Hall of Fame.

Over the course of his five-decade career, he won two Grammy Awards among 11 nominations in his career, with his songs recorded over the years by artists as diverse as Bette Midler, Serena Ryder, Dwight Yoakam, Marianne Faithfull and My Morning Jacket.

Prine was born on Oct. 10, 1946 in Maywood, Ill., and learned guitar from his brother. After finishing high school, Prine got a job as a postal worker in Chicago — «I delivered more junk mail than the junkyard would hold,» he would sing on 1995’s Ain’t Hurtin’ Nobody. He would later describe thinking of words and melodies on his mail route, and continue to write lyrics during a two-year stint in the army in the mid-1960s that interrupted his civilian employment.

Prine worked up the nerve to try out his songs on audiences in the late ’60s at open mic nights in Chicago.

«I got up there and never felt more comfortable in my life than when that spotlight hit me,» he told The Associated Press in 1978.

The likes of Kris Kristofferson and Paul Anka were impressed by Prine performances they caught at shows in Chicago and New York, helping to create momentum for a deal with Atlantic Records.

Raves for his debut

Prine’s self-titled debut in 1971, later included in Rolling Stone’s 2003 list of the 500 best albums ever, ushered in a songwriter of unique talent. Tearjerkers Hello in There and Sam Stone — about cognitive decline in seniors and the Vietnam War’s byproduct of drug addiction among vets, respectively — were tempered by light-hearted fare like the marijuana ode Illegal Smile. The rueful lyrics of Paradise, about coal mining’s impact in his parents’ birth regions in Kentucky, were sung to a rather joyous bluegrass sound.

Angel from Montgomery, with its beleaguered housewife, resonated with female performers: Bonnie Raitt, Carly Simon, Tanya Tucker and Toronto’s Leslie Spit Treeo would all record versions through the years.

By 1980, Prine had released six more albums, receiving plaudits for character studies like Souvenirs, Christmas in Prison and Storm Windows.

But he soon tired of the vagaries of big-label demands, relocating to Nashville and forming Oh Boy Records in 1981 with a couple of friends. In addition to his own recordings, the label began in the 1990s to release works by the likes of Kristofferson and Janis Ian.

Though critically acclaimed Prine’s albums were selling modestly. But a five-year absence and the opening of new radio formats for adult alternative and Americana music saw 1991’s The Missing Years greeted enthusiastically, with guest turns by Raitt, Tom Petty and Bruce Springsteen — all at or near the peak of their own commercial success — helping to create buzz.

That album’s All the Best, about the end of a relationship, became a particularly well-covered song through the years, while the title track pondered a question that has confounded religious scholars for hundreds of years — how Jesus spent his teen and early adult years. Among Jesus’ adventures, Prine reckoned:

«He discovered the Beatles /

«He recorded with the Stones /

«He even opened up a three-way package /

«In Southern California for old George Jones.»

Prine would tell Rolling Stone magazine he was flattered by a Grammy win for best contemporary folk album for The Missing Years, but when asked where he kept the trophy, replied: «On the mantle with a miniature bar, a little guy wearing lederhosen and an ashtray full of thumbtacks.»

Cancer battles

The follow-up Mixed Blessings and Lost Dogs (1995) was also well received — particularly for Lake Marie, an evocative song that often closed his shows, in which Prine seemed to bring all of his songwriting skills to bear: humour, nostalgia, a singalong chorus and an unpredictable change of tone in the song’s last verse.

Prine was touring to receptive audiences and gaining younger fans who were attracted to his material and humorous asides between songs, but was delivered a setback two years later when a tumour in his neck required surgery. When he re-emerged, the shape of his face and the tenor of his voice had been changed a result of the operation, but his loyal fans didn’t mind.

With characteristic humour, Prine in 2017 posted a «favourite»