Jazz history is often told through recordings and concerts. But sometimes the most revealing stories about musicians come from small, unexpected encounters — the kind of moments that show who these artists were away from the bandstand.
One of those moments was recalled by the great saxophonist Wayne Shorter, who once told a wonderful story about meeting one of his musical heroes… it was captured for a film about Lester Young called President of Beauty.
Stay tuned for the full story, plus a clip of the video…
Long before he became known for his work with Art Blakey, Miles Davis and Weather Report, Wayne Shorter was with the U.S. army. At that point he was simply a young musician on leave — and like many young jazz players, he was eager to hear the masters whenever he had the chance.
The setting was Toronto’s legendary Town Tavern, one of the most important jazz venues in Canada during the 1950s.
Shorter had ten days’ leave from the Army and decided to visit the club to hear Lester Young perform.
Watching a Jazz Legend Up Close
When Shorter arrived at the Town Tavern, the club was already packed.
He had dressed carefully for the evening — a pinstripe suit, paisley tie and the kind of sharp style that was common among jazz fans of the era. Like many musicians of his generation, Lester Young wasn’t just admired for his playing but also for his distinctive presence and personal style.
Soon Young entered the room.
Shorter remembered the scene vividly: Young moving slowly through the club wearing a long coat and his famous pork-pie hat, carrying his saxophone casually at his side. His posture was relaxed and slightly sloped, his movements unhurried.
It was the same unmistakable figure that audiences had seen for years on bandstands with the Count Basie orchestra and beyond.
Young eventually made his way to the stage and began playing.
Waiting at the Bar
While the band performed, Shorter stood at the bar hoping to order a drink.
But with the club so crowded, getting the bartender’s attention was nearly impossible. He realised it might take a long time before he managed to get anything.
Then something unexpected happened.
Shorter suddenly felt someone tap him on the shoulder. When he turned around, he was face-to-face with Lester Young. Young had apparently noticed him standing at the bar. Looking at Shorter’s sharp suit and New York style, he made an observation that immediately broke the ice.
“You look like you’re from New York,” Young said. Shorter confirmed that he was.
Then Young asked him a simple question: what he was drinking. Shorter replied that he wanted cognac. Young glanced toward the crowded bar and gave a calm, matter-of-fact answer.
“You won’t get it here.”
An Invitation Downstairs
Young then made an unexpected suggestion.
Instead of waiting for the bartender, he invited Shorter to follow him downstairs.
The Town Tavern had a wine cellar, and Young apparently knew exactly where to find something better than what the busy bar could provide.
So the two musicians went down into the cellar together. There, Young poured two generous glasses of cognac. Shorter later remembered that Young’s glass was even larger than his own. The two of them stood there talking casually during the band’s intermission.
At the time, Shorter was still a young man serving in the Army, on temporary leave from his duties. Sitting there with one of the most influential saxophonists in jazz must have felt surreal. As the conversation continued, Shorter found himself becoming increasingly tipsy from the generous pours of cognac.
Lester Young’s Calm Presence
What stayed with Shorter most strongly was Young’s distinctive calmness.
Young moved slowly, spoke quietly and carried himself with an easy, unhurried confidence. Even when it was time for him to return to the stage, there was no sense of rushing. Eventually Young simply said that it was time to go back upstairs.
Then he made his way back toward the bandstand, still moving at the same relaxed pace. Shorter watched him go. The whole encounter had lasted only a short time, but it left a lasting impression.
A Small Moment That Reveals a Personality
Stories like this offer a glimpse of Lester Young that goes beyond his recordings.
Young is widely recognised as one of the most influential tenor saxophonists in jazz history. His lighter tone, relaxed phrasing and melodic improvisational style helped reshape the instrument and influenced generations of players, from Charlie Parker to Stan Getz.
But anecdotes like Shorter’s story reveal something equally important: the personality behind the music.
Young was known among musicians for his unique language, his distinctive sense of humour and his quietly generous nature. The casual invitation to share a drink in the wine cellar fits perfectly with that reputation.
It also illustrates how accessible many jazz legends were in those days. The line between audience and performer was often thin, especially in small clubs where musicians and listeners shared the same space.
Watch Wayne Shorter Tell the Story
The video below captures Wayne Shorter recounting this memorable encounter with Lester Young.
Hearing the story in Shorter’s own voice makes the moment feel even more vivid — a young musician on leave from the Army, standing in a crowded jazz club, suddenly discovering that one of the great figures of the music is standing right behind him.
Looking for more? Check out our pick of essential Lester Young recordings here, or find more videos via our Jazz History page.