Jackie Leven, The Borderline, London

In these days of YouTube clips and webcast concerts, it takes more than competence and attitude to get paying punters to brave the drizzle and murk and come out to see your show, particularly if you're a troubadour blessed – or cursed – with an appreciation of the value of melancholy.

Jackie Leven is one such, perhaps our greatest musical poet of loss, his songs keenly anatomising the slight but significant shifts of mood, memory and emotion from which we construct our personal histories: not, perhaps, the most attractive prospect after a long day's labour. But Leven pulls a decent crowd, mostly comprised of lived-in faces world-wearied enough to appreciate the ebb and flow of life's fortunes. Or, as he puts it in "My Old Home": "Kingdom come, kingdom go – how that works, I just don't know."

To lure an audience, and keep them attentive, the touring troubadour has always had to develop a rapport more akin to a stand-up comic. Fortunately, Leven has a colourful past to draw upon, and the ironic delivery to put across his fund of offhand gags and observations, tales of scary acquaintances (such as the Irish transsexual hitman who provided the inspiration for the title-track of his latest album Lovers at the Gun Club), and the recollected wisdom of hecklers – his favourite putdown, he confides, came from a Glaswegian who greeted one of several songs about his late father with a scathing: "Typical Fifer, showboating about how he knew his dad!"

The song to which he may have been referring features Leven returning to the family home but finding no release from the estrangement that clouded their shared history. "Got a head full of headstones, as I stepped down from the train," he sings, about as perfect an evocation as has ever been coined of the sinking feeling brought on by familial duty that involves grimly rooting through the baggage of one's past. So: not just your typical Fifer, then, but a rarer, more sensitive breed.

Elsewhere, the beautiful "Kings of Infinite Space" is introduced via scenes from an old episode of Columbo featuring Johnny Cash, and we get chapter and verse, including the protagonists' names burned so indelibly into Leven's memory, about the unrequited first love in the backstreets of Fife covered in "The Innocent Railway". And reflecting Leven's intense interest in poetry, "Her Arms are Full of Broken Things" incorporates verses from AE Housman and Charlotte Mew, among others, accompanied with wit and empathy throughout by a band whose purring keyboard pads, wistful harmonica and backing vocals provide the perfect sepia-tint settings for his narratives.