Kris Kristofferson, Festival Theatre, Edinburgh

“This song is for my kids – and all their Mommas.” Even at 74, Kris Kristofferson exudes the quietly satisfied air of experience of a man who has spent at least half his life drinking, shagging, smoking and strumming to his heart’s content, and now has a whole lot of good times (and plenty of bad) to draw from at will.

A former military man, sports champion and Rhodes scholar, his talent for raising hell was always balanced by his more literate side, and the musician who provided the obvious visual inspiration for the recent Jeff Bridges vehicle Crazy Heart long ago eased into elder statesman territory. In Edinburgh last night his hair matched the silver of his harmonica and his clothes were as black as the sparse stage setting. His only prop was a music stand containing his set list, his handkerchief and his bottle of water (soft drinks only these days).

Kristofferson is now 74 and certainly sounds – if not looks - every inch of it. Many times last night I was reminded of that old Willie Nelson gag: just before going on stage for a Highwaymen gig in the Eighties, Kristofferson turns to Willie and says: “My voice isn’t in such great shape tonight.” “How can you tell?” quips Willie. And it’s true, a two-hour solo set from a man whose pipes were never exactly versatile and which these days could be kindly described as rudimentary might have been a daunting prospect.

In the end it was rather moving and valedictory, if not without its struggles. He often got by on sheer goodwill, displaying a wry gift for comedy and a self-deprecating manner that made his stumbles easy to forgive - which was perhaps just as well. There were forgotten lines and fluffed chords, and his guitar-playing frequently sounded like he was leafing through A Beginner’s Guide to Six Easy Chords while wearing a pair of boxing gloves; there were moments so ramshackle that I found myself glancing around the stage searching for a cloth cap with a scattering of loose change thrown inside. He even survived a momentary slip when he announced that he was back in England, a gaffe that would see most other performers skinned alive and hung out for the seagulls on Waverley Bridge.

But when he found his feet and really leaned into his songs, Kristofferson dug deep into the emotion of the words. And what words. Kristofferson has written more great lines – never mind songs – than perhaps any other Nashville alumni, the epigrams scattered like jewels among the plainest of musical settings. He also has a gift for gracefully merging the political, social and personal without showing the join. “The Circle” drew a line not only between the dead in Iraq and Argentina’s Disappeared, but also between Chomsky and Charley Pride - this was sophisticated global commentary set to the most traditional three-chord honky tonk blues imaginable.

“Nobody Wins” was framed by a jibe about Dubya and Cheney singing to each other in the shower; Bill Clinton didn’t get away scot free, either, although the jury is apparently still out on Obama – perhaps his next Don Was-produced album will shed some light. His last two records, The Open Road and Closer to the Bone, have been solid and sometimes excellent, but it was the early stuff that really resonated last night, the songs Kristofferson wrote in the late Sixties and early Seventies when he was busy turning Nashville on its head.

“Sunday Morning Coming Down” was quietly devastating, a hymn to loneliness in which all the senses conspire against the heartsick protagonist. The regretful, rueful love notes of “Help Me Make it Through the Night” and “Loving her was Easier” may have been slightly arthritic, but they took on an extra poignancy with age. “The Pilgrim” sounded suspiciously like a mythologised self-portrait, although he dedicated it to “all of us”, “us” being the likes of Dennis Hopper and Johnny Cash rather than "us" mere mortals. “Me and Bobby McGee” was solemn and stately.

Elsewhere, there were searing indictments of Native American injustice, sentimental odes to his kids, songs about junkies and juiceheads and living “on the other side of nowhere”, many recollections of love too easily won and too carelessly lost, and a few ribald comedy turns. By the time he got to “For the Good Times” and “Why me, Lord”, you realised that the entire concert was really just one long song. “True story!”, he often grinned after detailing some hair-raising exploit, and it became apparent that the spare musical structures and unfussy performances were a necessity, a deceptively simply scaffold expressly designed to frame the complexities of a tangled life unfolding imperfectly over the course of two strangely compelling hours. Messy, perhaps, but strong and true.

• Find Kris Kristofferson's Please Don't Tell me How the Story Ends on Amazon

Kris Kristofferson and Johnny Cash sing "Sunday Morning Coming Down" in 1980: