Jesse Winchester

Yankee LadyJesse Winchester
SnowJesse Winchester
BiloxiJesse Winchester
Do ItThird Down, 110 To Go
Mississippi, You're On My MindLearn To Love It
Nothing But A BreezeNothing But A Breeze
A Showman's LifeA Touch On The Rainy Side
Well-A-WiggyHumour Me
That's What Makes You StrongGentleman Of Leisure
EulalieLove Filling Station


Jesse Winchester playlist



Contributor: Peter Viney

Jesse Winchester’s career suffers somewhat from such an overpowering first album, that it was hard to live up to, though one of the pleasures of doing this Toppermost has been playing the complete albums again, rather than sticking to my selected iTunes Playlist which was done a few years back. I’d forgotten how much I loved all of them. In retrospective, they’re all stronger than I remembered, and I’ve deliberately spread this across the catalogue. I also realized I’m pretty much word perfect on the first album, and not far off on the second.

Winchester was born in Mississippi, moved to Memphis then went to Canada to avoid the draft. That stalled his career, as until Jimmy Carter’s amnesty in 1977 he could not enter the USA. By then he was a Canadian citizen, and Carter amended the first amnesty which ignored anyone who had taken foreign citizenship to include him. He is probably better known as a songwriter (Brand New Tennessee Waltz, Biloxi, My Songbird, Rhumba Man, Defying Gravity, Mississippi You’re On My Mind) than singer.

The first album was on Ampex in 1970, with a soft gatefold Bob Cato designed sleeve, repeating the same iconic photo four times, and was produced by Robbie Robertson after The Band (aka the brown album) and before Stage Fright. Todd Rundgren was the engineer, and that was how Rundgren – introduced to Robbie as “a young studio whizz kid” – went on to do Stage Fright. Robertson and Levon Helm (mandolin and drums) both played on the album. For years I’ve filed my copy in The Band section of my CD shelves. The album contains Yankee Lady, his best known song, chronicling a winter in Vermont and an escape to Mexico. Then there’s Snow co-written with Robbie Robertson, a song of a Southerner in exile if ever there was one:

I’d take a plane right to sunny Spain
Oh, but I don’t have the dough
But I’d build a bridge and I’d walk there
To get away from all that snow

If Yankee Lady is his best known song in his own version, then Brand New Tennessee Waltz may be his most covered song (Everly Brothers, Joan Baez, Patti Page, Matthews Southern Comfort, The Walker Brothers, Pure Prairie League, Ralph Stanley, Sweethearts of The Rodeo). Biloxi is a soft yearning for the Mississippi town, later covered by Jimmy Buffett. Southerner in exile is the recurrent theme through the early albums. Payday and The Nudge are out and out rockers, the latter sounding like Link Wray. Quiet About It sounds so much like The Band it’s uncanny, though Robbie’s distinctive guitar helps the illusion, as does Ken Pearson’s organ playing. Pearson was then in Janis Joplin’s Full Tilt Boogie Band with future 90s Band member Richard Bell. That’s A Touch I Like is a jaunty cheerful ditty while Black Dog is chillingly atmospheric. Skip Rope Song sounds like an English folk song. Every song on the album is worthy of inclusion.

Third Down, 110 To Go (1972) is stripped of the supporting cast of the first album; the songs are unadorned, tender, movingly sung. Do It (Do it, till we’re sick of it, Do it till you can’t do it no more) and Dangerous Fun are the two I’m struggling to choose between. Dangerous Fun has the lyric, perhaps. But Do It is one that stays in your head all day after hearing it. Midnight Bus has that great driving rhythm, and when the album was new, it was definitely my favourite track, along with God’s Own Jukebox, but time has led me to the quieter ones. And looking at the pile of CDs on my desk, I can’t afford two from any of the later albums.

Learn To Love It in 1974 has Mississippi, You’re On My Mind which demands its place. It also has covers of two Russell Smith songs for The Amazing Rhythm Aces, Third Rate Romance and The End Is Not In Sight (The Cowboy Song) but I’d go for the Amazing Rhythm Aces originals. He also does the traditional Tell Me Why You Like Roosevelt, inserting a verse about Pierre Trudeau at the end. Defying Gravity has a soaring vocal and would be the first or second choice from this album, if it hadn’t been beautifully covered by Emmylou Harris on Quarter Moon In A Ten Cent Town.

Let The Rough Side Drag is 1976 and Everybody Knows But Me is the one he put on his Best of. I felt we¹re getting too much into well-played, impeccably sung J.J. Cale territory around here … a bit samey. The title track was covered by Rodney Dillard and appears on Jesse’s live albums. The languid, brassy Step By Step featured in The Wire and is also on the soundtrack compilation.

Nothing But A Breeze in 1977 has a bigger band, and supporting vocals from Emmylou Harris, plus Canadians Dianne Brooks and Ann Murray. James Burton (on the title track), Glen D. Hardin and Ricky Skaggs all make appearances. The best-known song is Rhumba Man, due to covers. Nothing But A Breeze itself has that delicate James Burton work all over it: Me, I want to live with my feet in Dixie and my head in the cool blue North. My Songbird is assisted by Emmylou Harris, who recorded it herself, also on Quarter Moon In A Ten Cent Town. It’s one of his great compositions, but let’s save it for a potential Emmylou Toppermost. Twigs And Seeds is an amusing complaint, drifting in to Kinky Friedman or Loudon Wainwright III territory.

Nothing But A Breeze sold well, and at last Jesse could get back into the USA, so Albert Grossman, his manager, had him straight down to Nashville for the follow-up, A Touch On The Rainy Side (1978) produced by Norbert Putnam of Area Code 615 with a cast of thirty musicians. Jesse has said he felt intimidated by the no-expense-spared production. It starts off with A Touch On The Rainy Side which begins like Buddy Holly with a full orchestra, and it is perhaps overproduced for the intimacy of the song. A Showman’s Life keeps the orchestra back for a couple of verses. Great road-weary song. The fun one is a cover of Tony Orlando & Dawn’s pop hit Candida perhaps a comment on the new process he found himself in after the quiet years north of the 49th Parallel. The album is worth hearing because the backing, though swamping him compared to the bare earlier albums, is pretty damn good. Think Lyle Lovett … try the funk guitar and horns on Sassy and High Ball or the gospel with chorus of I’m Looking For A Miracle.

The next excursion was Talk Memphis produced by Willie Mitchell in 1981, in the town where Jesse grew up, Memphis. Say What became his only Top 40 hit. If another couple of selections were available, the title track Talk Memphis would be in the ten selections. A near miss.

After that, Jesse slipped out of major label territory, with a long gap before Humour Me in 1989, mainly recorded in Nashville with a ‘Newgrass’ dream team of Sam Bush on mandolin, Béla Fleck on banjo and Jerry Douglas on dobro. I love the opener, If I Were Free, a distinctive Jesse Winchester melody with gentle backing. Humour Me is another beauty. Well-A-Wiggy was the only track recorded in Montreal and is a pastiche late 50s pop song, and it’s so much fun that it gets the place for this album.

It was another ten years until Gentleman of Leisure in 1999, produced by Jerry Douglas. Steve Cropper does a couple of guest spots, setting the groove on Club Manhatten in which he is namechecked. Vince Gill is harmonising on Just Because I’m In Love With You. That, and No Pride At All both sound surprisingly like Roy Orbison! The one for the list is That’s What Makes You Strong with backing from Jonell Mosser who has sung behind a long list of singers.

Love Filling Station has let another decade slip by, still recorded in Nashville with Jerry Douglas. The four tracks I had on my “Best of 2009” playlist are Eulalie, O What A Thrill, Bless Your Foolish Heart and a cover of Stand By Me. The radio play song was Sham-A-Ling-Dong-Ding which is a soft ballad, not the oldie style the title suggests. The one I played most was Stand By Me (the violin is amazing) but I’ll take an original Eulalie. Or O What A Thrill. Toss a coin again. Eulalie.

There are several live albums, the most easily obtainable being Live From Mountain Stage in 2001 (which shows that Eulalie long predates Love Filling Station.) It’s solo with guitar. A trawl on YouTube will turn up several excellent live performances.

When Winchester was seriously ill in 2011, a tribute CD Quiet About It appeared with James Taylor, Lucinda Williams, Jimmy Buffett, Little Feat, Lyle Lovett and Elvis Costello covering his songs, and four of the eleven are from the first album. Jimmy Buffett organized the album, and did an excellent Gentleman Of Leisure. Little Feat had backed Nicolette Larson’s 1978 hit with Rhumba Man and reprised it. Allen Toussaint chose the least well-known song, the haunting and gentle I Wave Bye Bye another from Gentleman Of Leisure. Roseanne Cash’s take on Biloxi is the outstanding one for me, with deep horns like ship foghorns in the Gulf. Lucinda Williams makes Mississippi, You’re On My Mind sound like an outtake from Car Wheels On A Gravel Road. James Taylor’s Payday reminds me that Jesse and James have a similar vocal style. The sleeve note quotes Elvis Costello (who does the title track): it is quite remarkable how every song in this collection fits the style of each singer so well that you could swear he or she wrote it. It’s one of my favourite tribute albums.


Jesse Winchester (1944–2014)


Jesse Winchester, the Songwriter, Fanclub

Memphis Music Hall of Fame: Jesse Winchester

Jesse Winchester at Discogs

Jessie Winchester biography (Apple Music)

Peter Viney has been an educational author and video scriptwriter since 1980. He has written articles on The Band, Van Morrison and Bob Dylan. He also writes novels under the name Dart Travis and writes on popular music, theatre and film at his website.

TopperPost #165


  1. Kasper Nijsen
    Jan 13, 2014

    Thanks for filling in some of his story. I’m a huge fan of the first album, especially Biloxi and Yankee Lady, with that beautiful line about ‘An autumn walk on a country lane, and a million flaming trees, I was feeling uneasy ’cause there was winter in the breeze’. Maybe I’d try to include Little Glass of Wine from Learn to Love It as well.

  2. Peter Viney
    Apr 7, 2014

    Just heard the sad news that Jesse Winchester had passed away. RIP.

  3. Kasper Nijsen
    Apr 7, 2014

    I just heard the same. Sad news indeed. I’ll put on his first record tonight: “so have all of your passionate violins play a tune for a Tennessee kid”.

  4. Keith Shackleton
    Apr 7, 2014

    Apparently tales of his demise were premature… he is very ill though.

  5. Peter Viney
    Apr 14, 2014

    I listened through that magic first album in memory. See this link to the Peter Stone Brown archives with an excellent article on Jesse Winchester.

  6. Michael Simmons
    Apr 14, 2014

    Good overview of the late, great Jesse — thank you Peter. As I wrote on Peter Stone Brown’s site, few were capable of as much sound and fury while being so goddamn quiet about it. My favorite lesser-known Jesse song is “The Only Show In Town” from Let The Rough Side Drag:
    Maybe life is just put on for show
    Oh but it’s the only show in town
    It don’t cost a nickel to get in
    Oh but you pay dear to hang around

  7. Peter Viney
    Sep 17, 2014

    Jesse Winchester has a posthumous album, “A Reasonable Amount of Trouble” out in September. Reviews are excellent. ‘A Little Louisiana’ is picked out as the key track.

  8. Rod Moss
    Jul 19, 2019

    Great song choice and overview Peter, much appreciated.

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