I was already a huge fan of Jesse Winchester when in 1977 my then pregnant wife, Kathryn, and I went to see him in concert at Bogarts, a small venue in Cincinnati. Winchester was a draft evader that had gone to Canada in 1967. He was allowed to return to the US after Jimmy Carter’s amnesty for draft evaders in 1976. Kathryn was resplendent in a long white muslin dress with our first child inside her protruding belly. I was never prouder to be out with her. We arrived late and it appeared every seat at every table was occupied. Undeterred, we ventured down front to discover that a small table with three chairs right in front of the middle of the stage was empty. We couldn’t believe our luck. It was one of those meant to be moments. It was like having the band in your living room. With the intimacy of the closeness to the band, it remains to this day one of my all-time favorite concert performances.
I first became aware of Jesse Winchester when, after the breakup in 1970 of the Lemon Pipers (for whom I played bass), I moved to Wilmington Vermont with a three piece group I had formed with my best friend from high school. The band failed and I moved in with a group of hippies, one of whom became my beautiful wife. We will soon be celebrating 53 years together.
It was there that I was turned on to Jesse’s Winchester’s self-titled classic 1970 eponymous first album. It was produced by Robbie Robertson and recorded by Todd Rundgren. It contains The Brand New Tennessee Waltz, the first song he ever wrote, Yankee Lady (a favorite), and the haunting Quiet About It. It’s the place to begin if you’re not familiar with Winchester.
His 1972 release, Third Down, 110 To Go, is my favorite of all his albums. It displays the beautiful lyrics, simple arrangements and minimal instrumentation that are typical of all his recordings. It is near perfect in it’s deceptive simplicity. Just listen to it. Bob Dylan once said, “You can’t talk about the best songwriters and not include [Jesse Winchester] ”.
The 1974 release, Learn To Love It, has the catchy and endearing Third Rate Romance written by Russell Smith, later of the Amazing Rhythm Aces. The heartfelt Mississippi You’re On My Mind shows the fondness Winchester had for his southern roots.
In 1976 he released Let The Rough Side Drag. The title song is a lyrical expression of his philosophy of life. I find all his songs both poignant and uplifting. The album ends with a reprisal of his first song, The Brand New Tennessee Waltz. It was eventually covered, as were many of his compositions, by Joan Baez, Ralph Stanley, the Everly Brothers and Patti Paige, who had recorded the original Tennessee Waltz 50 years earlier.
Nothing But A Breeze 1978 contains Twigs and Seeds, a humorous plea for ganja legalization, and a nifty little tune titled Rhumba Man. The album features a who’s who supporting cast of Ricky Scaggs, James Burton, Emmylou Harris, Ann Murray and Nicolette Larson.
1981’s Talk Memphis showed his special affinity for Memphis, as his family moved there from Mississippi when he was six. He was influenced by the sounds of rhythm and blues and rockabilly via radio stations like WDIA and WHBQ where Dewey Phillips was playing the mixture of black and white artists that came to characterize Sun and Stax Records. The title song Talk Memphis is an homage to this early influence. This album also contains his only US Top 40 single, Say What.
In 2007 he received a Lifetime Achievement Award from the American Society of Composers, Authors and Publishers.
In 2009 he released his tenth studio album, the well-received Love Filling Station.
In 2012 a tribute record to Jesse, Quiet About It, was released that featured Jimmy Buffett, Elvis Costello, James Taylor, Lye Lovett, Roseanne Cash, Allen Toussaint and Lucinda Williams.
Jesse Winchester passed away in 2014. His final album titled A Reasonable Amount Of Trouble was released later that year with liner notes by his friend Jimmy Buffett, who recorded six of Winchester’s songs over the years. The record was nominated for two Grammys. Rolling Stone called it “one of the most moving, triumphant albums of Winchester’s 45 year career “ and “a gentle collection of playful songs about love, memory and gratitude”. The same could be said for most of the songs he ever wrote.