The Rhumba Man Sings No More: A Jesse Winchester Appreciation

I don’t know when the term “singer-songwriter” came into vogue, but it’s difficult to think of anyone who defined the very essence of that term as cleanly and clearly as Jesse Winchester, he of the impeccably rendered lyrics, near perfect diction, lovely simple melodies and sincere, affectless stage presence.

Winchester died on April 11, just about a year after I gravitated to his music for my shortest ever blog post in the wake of the Boston Marathon bombing. At the time, his soothing and tender balladry seemed just the prescription for a tormented national psyche.

Winchester engendered a deeply devoted following over his nearly 45-year recording career. That career took a distinctive turn very early on when he opted to go to Canada in 1967 rather than respond to a draft call that might have seen him pressed into service in Vietnam, a war he considered morally repugnant. He thought he was leaving forever, but President Carter’s amnesty allowed him to return for visits, though he stayed in Canada (Montreal) until 2002, when the love of a good woman drew him back to his homeland for good.

Winchester was a deeply humble and gracious man, deflecting all talk of heroism for standing up for his beliefs and abjuring all glitz and artifice in his writing and performance.

A man in a sweater, strumming a guitar on a stool, singing always from his heart; that was Jesse Winchester.

Or as a friend of mine and devoted Jesse fan described his music: “Clean, clear, simple, deep and beautiful.”

Winchester’s lifelong quest was to search his heart for a purity of feeling that always probed the essence of basic human emotion and experience. First love, mature love, love of place and people and playfulness, the cherishing of memory and its details —these made up nearly his entire oeuvre.


When I learned of his death, I was not alone in feeling suddenly bereft, as if I had lost a dear friend. This struck me as both weird and wonderful, given I’d seen him in concert only once and never had any other interaction with him over the years. But that statement misleads, ignoring as it does the intense and repeated interactions that take place between singer and listener, writer and reader, painter and viewer, in a kind of intimate dance that defies all conventions of “relationship” as we know it. With an artist who regularly bares his soul and invites you along as Jesse did, the “relationship” one develops with him or her is palpable and life-enhancing, and its loss is real and acute.

Fortunately, his music lives, his voice will go silent no time soon. Please consider yourself invited to partake in a few wisps of it below.


In an interview a few years ago, Winchester cited Sham-A-Ling-Dong-Ding as the favorite of his own songs. The playful title belies the song’s deep emotional resonance wrapped in a compulsively hummable tune. And the poetic rhythm is like a gentle force of gravity that invites a leaf to flutter to the earth, nestling into a crevice designed just for it. The first stanzas:

The boys were singing shing-a-ling
The summer night we met
You were tan and seventeen
O how could I forget
When every star from near and far
Was watching from above
Watching two teenagers fall in love

The way we danced was not a dance
But more a long embrace
We held on to each other and
We floated there in space
And I was shy to kiss you while
The whole wide world could see
So shing-a-ling said everything for me



Departing from the quietude and proving he had rock chops even if he didn’t much exercise them, Winchester joined his big fan and admirer Jimmy Buffett on stage in 2010 to sing his classic Rhumba Man in front of a far larger and more boisterous crowd than was his norm.




Finally, this searing song of departure and enduring hope serves as a sort of elegy for a consummate artist now stilled by the inexorable march of time and death. Full lyrics just below.



I Wave Bye Bye

Just out in the harbor
All the ships asleep
Maybe one cold watchman
Walks a lonely beat
Way out on the water
A ship is under sail
Leaving wavy starlight
And a dreamer in her trail

I wave bye bye
I pray God speed
I wish lovely weather
More luck than you need
You’ll only sail in circles
So there’s no need to cry
No, I’ll see you again one day
And then I waved bye bye

The sailing ship reminds me
Of a certain girl
Who left a certain dreamer
To sail into the world
I’ve very friendly postcards
From very far away
But they just remind me
Of a certain day

I wave bye bye
I pray God speed
I wish lovely weather
More  luck than you need
You’ll only sail in circles
So there’s no need to cry
No, I’ll see you again one day
And then I waved bye bye


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Appreciation for the rotating banner shots at top of page to Elizabeth Haslam, some rights reserved under Creative Commons licensing, see more at:

Grateful acknowledgement for lyrics rights copyright Jesse Winchester, all rights reserved, used by permission of KCA Artists, Nashville ( See also or

4 comments to The Rhumba Man Sings No More: A Jesse Winchester Appreciation

  • loweb3  says:

    The name certainly seems familiar, but I’ll have to admit that “Rhumba Man” is the only song I recognize. This reminds me of how I felt when Bobby Bland passed away recently. It was like a part of my life had died with him. Amazing that we can identify so closely with someone we’ve never really had personal contact with.

  • Lisa  says:

    Wow, what a wonderful voice. I had never heard of him, sad that his life was cut short. :-(

  • Andrew Hidas  says:

    Loren & Lisa, I’m glad to say I barely scratched the surface of his music here, not even mentioning a bunch of favorites like “My Foolish Heart” and “Brand New Tennessee Waltz,” “Looking for a Miracle,” “Mississippi You’re on My Mind,” etc. He compiled quite the wonderful American songbook. Some You Tube versions are better than others, but his voice and lyrics are so pure and evocative that he probably comes across best on audio, with the sound doing his music full justice.
    Loren, I knew barely anything about Bobby Bland when I saw he passed, but I’ll go looking now.

  • Pete Jameson  says:

    Thanks for the tribute. I first heard “Twigs & Seeds” back in ’77 and immediately bought the “Nothin’ but a Breeze” lp. I would add “Bowling Green” and an unreleased song he opened with when I saw him in NJ in ’09 called “Never Forget to Boogie” — due out this summer on the posthumous release, A Reasonable Amount of Trouble (Appleseed). Here’s a nice piece from May ’09:

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