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  • Writer's pictureThe Sound Cafe

Leon Redbone: Who Was This Mysterious Man? And Why We Should All Let The Mystery Be

By Richard Flohil.

Just before the reclusive singer Leon Redbone died two years ago — from Alzheimer’s and dementia — he wrote his own obituary.

“It is with heavy hearts that we announce that Leon Redbone (has) crossed the Delta for that beautiful shore, at the age of 127… he is interested to see what Blind Blake, Emmett (Miller) and Jelly Roll (Morton) have been up to in his absence…to his fans, friends and loving family who have already been missing him so in this realm, he says ‘Oh, behave yourselves. Thank you, and good night.”

And so, with a twirl of his cane and a tip of his hat, the world’s most enigmatic artist left us.


What Redbone had done for more than 45 years was to reinterpret American early popular music. His repertoire included Lonnie Johnson’s “Jelly Roll Baker,” nursery rhymes like “Polly Wolly Doodle All the Day” and “Camptown Races,” early blues from now-forgotten pioneers like Blind Blake, jazz songs from the Original Dixieland Jazz Band and Jelly Roll Morton, and classics from the exhaustive catalogues of the Gershwin's, Irving Berlin and others who gave us the “Great American Songbook.”

In performance, he remained completely unpredictable.

In a deep, rumbling voice he could give his listeners a learned dissertation on the pioneer role of the Original Dixieland Jazz Band and its leader, Nick LaRocca. “This man was the originator of jazz. He made the very first jazz records. Does anyone remember him today? No-o-o-o…”

He might show his audience an 8X10 publicity photograph of actress Barbara Eden and Hawaiian musician Don Ho (“Taken at Pismo Beach,” he explained). “Wonderful people; look at them… so happy!”

At a major concert at Toronto’s Ontario Place, he was introduced and slowly walked to the centre of the stage. Pulling up a chair, he put down a small tape recorder, adjusted the microphones close to the machine, and pressed the on-button. As the recorder played Greek and Egyptian songs, he slowly walked off stage.

Twenty minutes later, as the tape ended, he walked on stage to perform his set. The bemused audience gave him a standing ovation.


“Mr. Redbone,” enthused the young man, earnestly engaging the mysterious artist in conversation. “I have written this song that would, sir, be perfect for you. It’s about the impact of early popular music on the young generation, and the melody is reminiscent of songwriters like Cole Porter and Irving Berlin…”

Gently, Leon Redbone interrupted. “Very interesting,” he muttered in his slow, gravelly rumble. He paused as he looked up from his dinner in his dressing room.

“Was this song written before 1940?”


From his early days in Toronto, when he would make unannounced appearances at small folk clubs — I first heard him in 1970 at a midtown club called Fiddler’s Green — he rebuffed any questions about his real name, his origins, his age or any personal information whatsoever.

Asked these questions, his responses were unusually fanciful. ”I was born in Bombay,” he told one interviewer. “My parents were Niccolò Paganini and Dame Nellie Melba. Lovely people; they raised me well.” (Paganini, the virtuoso violinist, died in 1840 and Melba, the preeminent opera singer of her day, passed away in 1931).

He had always been reclusive. When he first emerged he was a reluctant part of the Toronto folk scene, and often played as a duo with a hot young local guitarist called David Wilcox. He soon differentiated himself from the earnestness that was the hallmark of the time.

In those days it was difficult to reach him — the best way was to call the pool hall that, back then, was located in the entrance to the Bloor Street subway station.

A request to speak to Mr. Grunt would bring him, irritated from having to interrupt his game, to the phone. “Yesss?” was his grumbled response.

Intrigued by the “mystery,” fans would follow him after he played a show; he would usually lose them on the way by suddenly changing buses or subway trains.

One friend drove Redbone “home” at 2 a.m. and dropped him at an apartment building. Watching in his rear view mirror, he saw the singer, carrying his guitar and a large black leather artwork portfolio, return from the lobby, jump in a cab and speed off in the opposite direction, presumably to his real home.

Redbone’s prowess at pool, was only matched by his skills with a deck of cards. Playing poker with Redbone was simply foolish; I remember watching him clean out Townes Van Zandt, Guy Clark and Rambling Jack Elliott at a late night gathering at the Winnipeg Folk Festival.

Another victim that night was the festival’s artistic director, Rosalie Goldstein. “I should have known…” she said ruefully after losing $60.00 and bailing from the game.


Redbone’s first major impact with larger audiences came at folk festivals. When Bob Dylan arrived unexpectedly at the Mariposa Festival on Toronto Island in 1972, the first person he asked for was Redbone.

Five hours later, with Dylan running backstage to avoid being mobbed by fans, they departed together. Redbone, wearing a dark suit, a western string tie and carrying a black umbrella to protect himself from the afternoon sun, impassively ignored the photographers trying to grab a shot of the two of them as they left the island on a police launch.


Eventually, he moved to the United States, made more than a dozen appearances on Johnny Carson ‘s late night television show, and made a fortune doing television commercials for Budweiser, Chevrolet, a Japanese whiskey, and Britain’s Inner City Rail.

His music was frequently used in films and on a number of television series. Along the way, he made 13 studio albums and half a dozen live and compilation records.

And he was even the subject of a Far Side cartoon.


When he died, The New York Times called him “a throwback singer” — a too-slick description of one of the very few artists who made old music new again.

But if his sly humour, deliberate deceptions, and his rumbling voice all helped make him famous, it also allowed the listeners emphasis to be where he wanted it — on the songs.

Which was the whole point of letting the mystery be.

Richard Flohil is completing a memoir; this piece is adapted from a chapter of his upcoming book, The Night Miles Davis Tried to Buy My Car.

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