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Jesse Winchester: An appreciation

He had a low profile compared to the artists who recorded his songs, but singer-songwriter Jesse Winchester, who died on April 11 at 69, was covered by the wide-ranging likes of Patti Page, Elvis Costello, Jimmy Buffett, Joan Baez, Anne Murray, Reba McEntire, Rosanne Cash, The Everly Brothers and Emmylou Harris--and loomed larger than most in the hearts of those who knew him.

Jim Della Croce (left) and Jesse Winchester.
Jim Della Croce

“I’m hard-pressed to come up with a more skilled songwriter than Jessie Winchester,” says John Sebastian, a member of both the Songwriters and Rock and Roll Halls of Fame for his work in the Lovin’ Spoonful. “Really hard-pressed.”

“I mean, you’ve got guys with your Bob Dylan skills, and guys-who-imitated-Dylan skills, but to me, Jesse was such a different creature,” continues Sebastian. “He really wanted to write concisely, and his songs were three- or four-minute chunks that you couldn’t take in on a jukebox. And I was always so amazed at how different each song was and how each one really expressed a new idea.”

Jim Della Croce, a publicist and artist manager who managed Winchester in the early 2000s and produced a Winchester retrospective concert in Woodstock, N.Y., also invokes Dylan.

“As a singer-songwriter, recording artist and performer, Jesse was the quintessence of style--and my Bob Dylan,” says Della Croce. “He lived at the heart of the human condition and will rank as highly as a writer as Frank Zappa does as a composer.”

Della Croce actually left college in 1977 to follow Winchester, who had moved to Canada in 1967 to avoid the Vietnam War draft, and returned after President Jimmy Carter’s amnesty in 1977 to play his first U.S. concerts in over a decade.

“He played music from his first few albums on Bearsville Records to packed houses across the country,” recalls Della Croce. “There wasn’t a music critic of consequence who wasn’t on hand and eager to salute him. I most vividly recall his full-band shows at New York’s Bottom Line and the Bijou Café in Philadelphia—which was captured as a live radio show and is available on disc.”

Winchester’s catalog, notes Della Croce, “is an unparalleled and timeless patchwork quilt of finely crafted songs that will endure as the benchmark not only for this generation of songwriters, but all those that follow. And he lived the ‘showman’s life’ as a performer: Waltzing through the clubs, cafes, listening rooms, theaters and festivals throughout North America—he was a quiet, gentle giant of music. He was doggedly determined to make his songs count.”

Hence, Winchester “often took years to complete projects to his own exacting standards,” continues Della Croce.

“Revered by such artists as Dylan, James Taylor, Jackson Browne, Bonnie Raitt, Emmylou Harris, Joan Baez, the Everly Brothers, Jimmy Buffett and Elvis Costello, Jesse remained humble and quietly content with his place in music. He had nothing to prove, and he loved and respected his peers and his loyal cadre of fans and admirers.”

In a highly personal and profound essay on his website, Costello, reflected on Winchester’s kindness “when as a novice musician I’d approached him in a London club in 1976 to tell him how glad I was that he had written ‘Midnight Bus’--as I could snare a restive crowd at the clubs and coffee houses that saw no charm in my own quiet songs, but would respond to that song or Jesse’s risqué and philosophical gem, ‘Do it.’”

Of Winchester’s self-titled 1970 debut album, Costello said that the songs “were better than ‘good’--they were as enduring and resonant a group of songs as any produced by his early ‘70s songwriting contemporaries who went on to sell records in the multi-millions. It is a mystery to me that this success eluded this most gifted, if self-effacing, of writers.”

Costello contributed liner notes for the Best Of Jesse Winchester compilation, performed the “Quiet About It” titletrack on the Winchester tribute album, and hosted Winchester in a 2009 installment of his music/interview TV series Spectacle.

“He both stole and stopped the show with an astounding rendition of his then current song, ‘Sham-A-Ling-Gong-Ding,’ which brought members of both the crew and cast to tears and left me speechless and almost unable to continue the taping,” wrote Costello. He also cited Winchester’s first composition, “Brand New Tennessee Waltz,” and its lines “When you leave it will be like I found you, dear/Descending Victorian stairs.”

“It’s an entire story line implied by 14 words,” said Costello.

Winchester’s “lessons of economy and brevity in song and grace, modesty and forbearance in life,” he added, “are not always examples that I have been able to apply to my own experience, but his songs and our brief but valued acquaintance will travel with me always.”

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