Winchester was born in Bossier City, Louisiana, his father being stationed at Barksdale Field. He was raised both in the country (on farms owned by his parents) and in the city of Memphis, Tennessee, and attended Williams College in Williamstown, Massachusetts, graduating in 1966. After touring Germany and upon receiving his draft notice in 1967, Winchester relocated to Montreal, Quebec. He became a Canadian citizen in 1973, and married his first wife Leslie. After many years in Montreal and after his divorce, he established his personal studio at Saint Georges de Beauce, Quebec, and resided there for some years before moving back to Memphis in 2002. Married to his wife Cindy, he lately resided in Charlottesville, Virginia. Winchester had three children from his first marriage, Alice Evangeline, James Ridout and Marcus Lee.
After playing with the Astronautes in Quebec, and while appearing as a solo performer in coffee houses throughout eastern Canada, he was introduced to Robbie Robertson (then of The Band ) and Albert Grossman (then manager of Bob Dylan). Winchester made his first album, the acclaimed "Jesse Winchester" (which included his classic 'Yankee Lady,' 'Brand New Tennessee Waltz,' and 'Biloxi') with Grossman as his manager and Robertson as producer, which was released on the Bearsville label. He subsequently toured in Canada as an opening act for The Band. Jesse went on his own road tour of Canada in 1973-74 along with drummer Butch McDade of the subsequently formed Amazing Rhythm Aces. He has completed tours of both Australia and Europe as a performing musician.
Winchester recorded sporadically on several labels since 1970. Unable to tour in the U.S. until the 1977 Carter amnesty, he subsequently became best known for his excellent songwriting, despite being an equally accomplished singer and guitar and Keyboard player.
Commonly referred to as 'legendary', and acknowledged as one of the premier tunesmiths of the late twentieth century, his songs include "Yankee Lady", "Rhumba Man", "The Brand New Tennessee Waltz", "Mississippi, You're on My Mind", "Defying Gravity", "Freewheeler" and "Biloxi." They have been recorded by numerous artists including Patti Page, Elvis Costello, Jimmy Buffett, Emmylou Harris, Joan Baez, Jerry Garcia, Jerry Jeff Walker, Wilson Pickett, Jimmie Dale Gilmore, Reba McEntire, David Ball (country music), Bonnie Raitt, Everly Brothers and Brewer & Shipley but his self professed favorite rendition of any song covered is that of Ed Bruce in his rendition of "Evil Angel".
Winchester's song "Step by Step" from Let the Rough Side Drag was used in the final episode of HBO's 'The Wire's first season.
While there was grace and gentle humor in Winchester's writing, his body of work also reveals an undercurrent of darker forces. His vantage point is often that of the outsider, longing for the South, restless, and willing to betray those he loves for the freedom of the road. The protagonist in Yankee Lady callously abandons the woman who takes him in, just as the singer in Freewheeler warns that he "would ride rough-shod over lovers...time and time again." Temptation and the eternal struggle between good and evil converge in Evil Angel, "first you start 'em with a little...'til they just can't get enough."
Winchester studied German and philosophy as a young man, and his introspective nature was disclosed by his many references to life's essential dualism: "if you know you're weak...that's what makes you strong"(That's What makes You Strong); "if I were free...I'd run and lock myself away with you"(If I Were Free); "but one day the high must lay low" (Defying Gravity).
As a consequence of sporadic album releases, there was a high demand for his work leading to multiple releases of unauthorized recordings. Like many other artists, Winchester took a strong stance against the release of so called Bootlegs and actively urged his listeners to support only the "Original thing".
Winchester’s final CD, "A Reasonable Amount of Trouble", was released in September 2014, with liner notes by his friend Jimmy Buffett. The album was nominated for two Grammy awards.
Defying Gravity
Jesse Winchester Lyrics
Jump to: Overall Meaning ↴ Line by Line Meaning ↴
I never do dream I may fall
But even the day that I do
I'll jump off and smile back at you
I don't even know where we are
But they tell us we're circling a star
Well, I'll take their word I don't know
I'm riding a big blue ball
I never do dream I may fall
But even the high may lay row
So when I do fall I'll be glad to go
Jesse Winchester's song "Defying Gravity" is a reflective tune about the overwhelming feeling of living life on earth—riding a big blue ball that's constantly in motion. The lyrics hint at the idea that we're all just floating through space, and it's a very real possibility that we will eventually fall off. But even in the face of that uncertainty, Winchester remains optimistic, singing that he won't be afraid to jump off when the day comes. He'll even "smile back" at those left behind.
Throughout the song, there's a sense of detachment as the singer muses on the fact that he doesn't really know where he is or even where he's going. But despite the lack of understanding, he remains open to the possibility that everything will be okay. The repeated line, "I never do dream I may fall" speaks to the idea that we often take our existence for granted, going about our daily lives without stopping to consider the sheer improbability of our very existence.
Overall, the song is a meditation on the beauty and mystery of life on earth, and a tribute to the human spirit of resilience and hope. Even in the face of the unknown, Winchester reminds us that sometimes it's enough to simply hold on tight and enjoy the ride.
Line by Line Meaning
I live on a big blue ball
The planet Earth is where I reside.
I never do dream I may fall
I don't anticipate failing or losing my balance.
But even the day that I do
However, in the event that I eventually stumble or falter
I'll jump off and smile back at you
I will maintain a positive outlook and attitude regardless of the situation.
I don't even know where we are
I'm not certain of our current location in the universe.
But they tell us we're circling a star
I've been told that our planet is moving in orbit around a star.
Well, I'll take their word I don't know
I will trust their assertions despite my own uncertainty.
But I'm dizzy so maybe that's so
I am feeling lightheaded and disoriented, possibly confirming their statements.
I'm riding a big blue ball
Once again, I am situated on Earth.
I never do dream I may fall
I have no presentiment of falling or collapsing.
But even the high may lay row
However, success has its ups and downs, just like everything else.
So when I do fall I'll be glad to go
If I should fail or trip, I'll take it in stride and make the most of the situation.
Lyrics © Warner Chappell Music, Inc.
Written by: JESSE WINCHESTER
Lyrics Licensed & Provided by LyricFind