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.
Do It
Jesse Winchester Lyrics
Jump to: Overall Meaning ↴ Line by Line Meaning ↴
If the wheel is fixed
I would still take a chance
If we're treading on thin ice
Then we might as well dance
So I play the fool
But I can't sit still
To the top of this hill
Do it
'Til we're sick of it
Do it 'till you can't do it no more
Friends will pity you
I guess that's what they're for
But they just take you like they find you
When they find you on the floor
But you do it
Til you sick of it
Do it til you can't do it no more
The lyrics of Jesse Winchester's song, "Do It," seem to suggest that life is unpredictable and filled with risks. The singer urges us to take chances even if we're uncertain about the outcome. Using the metaphor of a wheel, the singer implies that life may follow a predetermined path, but it's still up to us to embrace the journey and enjoy it. Furthermore, if life is like treading on thin ice, then why not dance on it, make the most of a dangerous situation, and enjoy life to the fullest. The line "friends will pity you" suggests that even if we fail, we still have friends and people who care about us.
The lyrics are begging us to live life boldly and to take chances. The singer advises that we should keep going even when we feel like quitting. We should keep doing things until we're sick of them or until we can't do them anymore. The lyrics underscore the idea that we should make the most of every day we have, to take risks, and that it's better to have tried and failed than never to have tried at all.
Line by Line Meaning
If the wheel is fixed
Even if things seem predetermined, I would still take a chance
If we're treading on thin ice
Even if there's a risk involved, we might as well make the most of it
Then we might as well dance
If we're already on a risky path, then let's just have fun with it
So I play the fool
I may seem foolish to others, but I'm enjoying myself
But I can't sit still
I'm too excited by the prospects of taking risks and having fun to stay still
Help me get this rock
Assist me in achieving my goals, despite the difficulties ahead
To the top of this hill
Reach the highest point of success I can imagine
Do it
Just go for it
Til we're sick of it
Keep doing it until we can't physically or mentally handle it anymore
Do it 'till you can't do it no more
Keep pushing yourself to the limit
Friends will pity you
Your friends may feel sorry for you and see you as foolish for taking risks
I guess that's what they're for
But their role is not to stop you from taking risks and having fun
But they just take you like they find you
Your friends will accept you the way you are, even when you fail
When they find you on the floor
Even after you fail or fall, your true friends will still be there to support you
Til you sick of it
Keep on doing it until you can't anymore
Do it til you can't do it no more
Never stop taking risks and enjoying life to the fullest
Contributed by Nolan N. Suggest a correction in the comments below.
Paul Burich
Great talent died yesterday at 69. Beautiful voice, beautifully-crafted songs. Farewell and God's speed, Jesse.
Steve Shoemaker
Thank you for posting this outstanding piece from Jesse, may he rest in peace.
Michael Edwards
A lot of truth and beauty in this minute and a half song!
Cul Heath
So sad to hear of Jesse's passing.
Carolyn MCleod , Randy price and I had the opportunity to tour Quebec with Jesse in the very early 70's as a group called Moonstone. Jesse was an amazing talent and musical magician. The way he could capture the attention of an audience with his soft voice and small movements was astonishing.
We adopted "Do It" after hearing him play it on tour into our standard set.
If you want to hear a sample of our version there's an old partial live take at http://www.deeperwants.com/vids/music/thinice2.mp3
He was a major inspiration to all of us. Salut and peace,Jesse.
flamencoprof
As a drug-taking youth I heard this song as both funny and a wake-up call against excess. I was used to big rock songs about "going for it" and chasing some kind of high. This song sort of shocked me with its honesty and brought me back to earth.
Tony Deane-Shaw
Great inspiration and motivation
Paul Smith
Wonderful song, inventive upload... great combo genessa!
Gail Feldman
:-)) thanks!
g
Gail Feldman
oh yeah i went by genesssa and for some reason (nothing disciplinary) got locked out when the site changed hands, so i use my english name now. but it's still me!
g
b. west
Nice song.
I like Jesse's song writing. We are very short of good songsmiths.
Thanks for great job on the video.
Personally, I have a very hard time finding songs on YouTube. Know there are lots of his songs on this site but they just keep showing me the same ones over and over. The old YouTube was much better before Google screwed it up. You can not search it now like in the past
I can not find a good copy of his "Lonely for awhile", but know it is out there somewhere, that he is singing it..
Thanks, again.