I saw singer-songwriter Jesse Winchester perform on the St. Paul campus of the University of Minnesota more than 25 years years ago and he bowled me over. There couldn’t have been more than a hundred people in the audience. Accompanying himself on guitar, he turned in a beautiful performance that concluded with “Yankee Lady.” Although Winchester had famously evaded the draft by decamping to Canada in 1967, returning only after the Carter amnesty, there was not a hint of politics in his performance.
I try to appreciate the music and put politics to one side in these posts. I understand some people can’t. I shared Winchester’s feelings about the war at the time but am a little younger than he was and drew a high number in the draft lottery held in the summer of 1970. Luckily for me (because I was wrong), my convictions were never put to the test. Winchester committed his own views to a single autobiographical verse in his adaptation of “Tell Me Why You Like Roosevelt” on Learn To Love It in 1974.
Winchester died of cancer in 2014 at the age of 69. Jon Pareles has an account of Winchester’s career in the New York Times obituary. Bob Mehr took an extended look in the Memphis Commercial Appeal obituary. Winchester was a fraternity brother of William Bennett at Williams College. As I recall, Bill spoke warmly of him when he passed in 2014. The anniversary of his birth this coming Tuesday affords an opportune moment to remember him with the resources of YouTube.
Winchester grew up in Louisiana, Mississippi, and Tennessee. He spoke with an endearing Southern accent that seems to me, in Winchester’s case, how American English should be spoken. You can hear all the crosscurrents of American popular music in his songwriting and in his singing. Country, blues, rock, soul, and gospel — they’re all there.
Winchester’s songwriting was appreciated by fellow musicians such as Wynonna Judd. Wynonna recorded Winchester’s gospel-tinged declaration of faith — “Let’s Make A Baby King” — on Tell Me Why (1993), along with Winchester’s “Just Like New.” The album’s ten cuts generated five hit singles, but Wynonna’s version of “Let’s Make a Baby King” reached number 61 on the country chart based on unsolicited airplay.
Winchester had a dry sense of humor that he drew on for many of his songs. Interviewing musician Herb Pedersen in 2014 and knowing Winchester was close to death, I asked Herb about the manifestation of Winchester’s sense of humor in his songwriting. “My goodness,” Herb said, “he could be funny pulling up his socks.” My intent this morning is just to recall his work and hit a few highlights.
Working the same vein that The Band had tapped into, Winchester could write songs that sounded like they’d been around forever. I thought “Yankee Lady” was an instant classic. The song was a highlight of Winchester’s self-titled debut album produced by The Band’s Robbie Robertson in Toronto in 1970. I think the live versions with Winchester accompanying himself on guitar display the song to better effect than the 1970 album version.
A songwriter himself, Robertson had been knocked out by what he describes in his 2016 memoir Testimony as the “powerful melancholy sweetness” in Winchester’s songs. You can certainly hear it in “Yankee Lady” and also in “Brand New Tennessee Waltz,” which I thought was another instant classic on the debut album Robertson produced. Those are the two songs Winchester played for Robertson in Ottawa at their first meeting. When Robertson told him he would help Winchester secure a recording contract and produce the album if he had time, Robertson writes, “He glowed with encouragement and looked like he was being rescued from a lost island, which in a way he was.”
The title of Third Down, 110 to Go (1972) reflected Winchester’s sense of humor, as did “Isn’t That So.” That is a statement in the form of a question.
“Let the Rough Side Drag” was the title track of his 1976 album. It’s an offbeat song of inspiration and appreciation. It’s funny too, but this is serious: “What a good thing to make a joyful noise.”
I thought Nothing But a Breeze (1977) was a strong album that should have put him over the top. One of the most striking cuts on the album was his cover of “Bowling Green,” by Terry Slater and Jacqueline Ertel. First recorded by the Everly Brothers for a single in 1967, it also appears on their Everly Brothers Sing album. Jesse’s cover does not suffer by comparison.
Jesse broke though during this period, but not at the level his talent merited. The live performance captured in the video below, for example, shows Jesse singing Martha Carson’s gospel number “You Can’t Stand Up Alone” with Emmylou Harris and Bonnie Raitt (originally recorded for Learn to Love It). He seemed to me to have everything necessary to be a star of the first order.
I caught up with Jesse again when he released Gentleman of Leisure in 1999. Beautifully produced by dobro virtuoso Jerry Douglas in Nashville, the recording showed Winchester operating in peak form with a fantastic set of his own compositions. Winchester’s dry sense of humor is all over the title track.
Winchester also wrote songs that expressed deep feeling with economy and restraint. The last song on the disc is “I Wave Bye Bye” (video below). It hits home for me with the force of revelation. I thought he must have written the song for Alice, his only daughter and youngest child, but Cindy Winchester (Jesse’s widow) gently corrected me. She advised that I had gotten that wrong in my own remembrance of Jesse on Power Line. Cindy cited “It Takes a Young Girl” (from Nothing But a Breeze) as the song he wrote about Alice.
We probably shouldn’t leave Gentleman of Leisure before we check out “Wander My Way Home.” Backed by the Fairfield Four, this is a Sunday morning song, Winchester style, with a sense of humor and a heaping tablespoon of metaphors.
Love Filling Station (2009) was Jesse’s last disc to be released before he died. Also produced by Jerry Douglas, the disc includes a moving cover of “Stand by Me.” The posthumous A Reasonable Amount of Trouble (2014) is also worth checking out.
As Winchester struggled with his first bout of cancer in 2011, fellow artists including James Taylor, Vince Gill, Emmylou Harris, Allen Toussaint, Jimmy Buffett, Rosanne Cash, Lyle Lovett and Rodney Crowell recorded the tribute album Quiet About It (now out of print but available on streaming services and on YouTube). Not too shabby. Indeed, I highly recommend it. Mac McAnally contributed a cover of Winchester’s “Defying Gravity” (I think that’s a pun), a number that goes back to Learn To Love It.
Elvis Costello was also a fan who contributed to the tribute album. Let’s not wave bye bye before we take a look at Jesse in performance on Costello’s old Sundance cable show. “Sham-A-Ling-Dong-Ding” — a song from Love Filling Station — testifies to the power of music in our lives. One can see the impact of the song on Neko Case, who sat beside Jesse staring straight ahead with a tear or two streaming down her face. “That’s it, Jesse,” Elvis commented. “You finished me off.”