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Willie Nelson performs at Massey Hall on Victoria Street in Toronto.Fernando Morales/The Globe and Mail

Outside Massey Hall at twilight, a crowd of fans and photo-snappers mobbed patiently around the door of the night-lifer Willie Nelson's bus. It is part of a quasi-Catholic ritual. People waited for a sweet cloud of smoke to emerge from the touring vehicle, which would signal the imminent appearance of a kindly balladeer – the Pope of Puff.

Which is what happened. The black-Stetsoned Nelson eased into sight, meeting expectations and autograph seekers as he made his way to the stage door, at no great rush. The eyes of the new octogenarian twinkled, curiously showing no signs of glaucoma. A few minutes later he was on stage, with no airs or introduction, singing and playing guitar, warming up on the fly. "It's been so long, but it seems like it was only yesterday," he warbled, his tone conversational, nasal and favourite-leather comfortable. "Ain't it funny how time slips away."

As it was in 2009 at the same venue, the band and staging was spare and informal: A drummer who made do with a single snare and brush or two, a tall drink of a bass player towering behind, a harmonica player hanging here, a woman (out of my view behind a grand piano) over there, and the bandleader in braids (whose mamma had let him grow up to be a cowboy) dead centre.

He sang Crazy. Was he? Yes, like a fox. A crazy fox.

The guitar he cradled was a Martin short-scale N-20 classical, one of less than 300 ever built. It was a battered relic – a battered relic – unintentionally equipped with an auxiliary sound-hole. The instrument is his partner, in the way that Charlie McCarthy was Edgar Bergen's. (They never spoke at the same time; the conversation entertained.)

Nelson, a Django Reinhardt enthusiast, was once voted the 77th greatest guitarist of all time by Rolling Stone magazine. The Gypsy-jazzer Reinhardt developed a unique style which compensated for the uselessness of the paralyzed third and fourth fingers on his chording hand. Nelson himself has long struggled with carpal tunnel syndrome, which perhaps manifests itself in a style one might call avant-garde. Or whimsically nuanced. Or charismatically idiosyncratic.

Or "jazzy," given that the concert unofficially opened this year's Toronto Jazz Festival. (On Friday, Nelson's schedule had him at the jazz affair in Ottawa.)

Like naked emperors who wear the best clothes imaginable, Nelson offered up bizarre guitar shapes and stabs that drew applause. His chord-bunching was unsubtle; his phrasing, abrupt. Single-string runs were strangely done – his awkward way involved touching twangily at notes in rudimentary progressions, feeling his way like one would hit each step when walking down stairs in the dark, making their way until the floor (or desired root sound) was arrived at. My eyes loved watching it, though my ears were puzzled.

The piano player was identified as Little Sister, who was Bobbie Nelson, whose style was saloon. Like her brother's guitar manner, sister's playing was deceptively masterful. She never hit four notes fluidly when she could hammer away stubbornly at one. There was a time when female country-swing pianists stuck to unsophisticated ways, so as to not show off unladylike virtuosity. Sister hid her skill well.

Nelson's run of classics and recent material (including his latest album Let's Face the Music and Dance) were generously received. He sang laconically about being on the road again, about big dogs moving it on over, about things on his mind (Georgia and you), and about good-looking women and what they might have cooking.

The sing-along of a Hank Williams gospel number was the finale. The band played on as Willie refused to walk toward the light he sang about. Instead the Texas longhair signed the bandanas he had flung out during the performance, and headed straight back on to the now fumigated bus, not wanting to wait to get back again on the road.

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