Jeff Healey

Jeff’s Last Train: A Jazzman’s Journey

Jeff Healey & Tyler Yarema Bill King Photography 1998

Some people are fortunate to recognize the passion of their lives and live every moment in pursuit. Jeff knew exactly why he was here and stayed true to the chase right to the end. He wasn’t just another musician looking for a break—he was a seeker, a craftsman, an artist of the highest order.

I remember reading about Glenn Gould’s late-night phone calls—those long, crafted, pointed exchanges where he dissected music and its purpose. Jeff had a similar intensity, a need to continue the conversation beyond the interview. After I spoke with him for the cover of Jazz Report, the calls kept coming. Days later, he’d ring with fresh observations, new insights, as if he had just uncovered another hidden layer in the music. He was an indie artist through and through, not because it was fashionable but because he had no choice—his music had to remain his own.

I once tried steering him back to the guitar, hoping he might revisit the instrument that had shaped his early years. He shook it off. “That chapter is behind me,” he said. I pressed, probed, searched for a clue to the mystery. But Jeff had already moved past the blues-based romps and three-chord resolutions. He heard something else in his head—something stripped of conceit, free from artifice. It was the sound of another era, the echo of a time before jazz had a name, before it was neatly categorized and marketed.

Jeff chased the essence of music, the moment before it was tamed. He wanted the rustic morning that gave birth to jazz, the raw energy that seduced men and women alike. He wanted to be at the turn of the century when Buddy Bolden stung the ears of parishioners with a cornet that needed no amplification, no effects—just breath and fire. His music wasn’t about technique or perfection; it was about soul, soil, heart, air—all colliding to create something new.

In his mind, he was traveling—living within the notes, reliving the stories of those who came before. Jazz, after all, is a conversation across time. It’s the marriage of blues, rhythm, folk, suffering, memory. It’s the music of slavery and starvation, of brothels and long-legged women, of dapper men with shoes shined bright as the moon. It’s about good times, bad times, and the never-ending road between them.

Jeff lived inside that history every time he raised his trumpet to his lips. In three and a half minutes, he could transport himself from Davenport, Iowa, straight onto a riverboat cruising the Mississippi. He could count the band in at a brisk tempo and suddenly be standing in the shadow of Louis Armstrong. His music had destinations—each note stamped with a travel order, a train schedule, and a departure time.

Then, one day, he caught the last train. And we know where it’s headed.

Somewhere, the band is waiting. Buddy’s got a new pal. And Jeff is finally where he always belonged—deep inside the music, playing for all eternity.