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.
It Takes A Young Girl
Jesse Winchester Lyrics
Jump to: Overall Meaning ↴ Line by Line Meaning ↴
It takes a young girl to make an old man smile
It takes a young girl to make an old man fly
Why should it take a young girl
To move this old heart of mine ?
It would take an old man too long to explain
But that's just how it is, first she's yours and then she's his
And that's always, always the same.
It's been ten long years since I've cried
It's been five, I know five since I've even tried
Now why should it take a young girl
To move this old heart of mine ?
But that's just how it is, first she's yours and then she's his
And that's always, always the same.
Jesse Winchester's "It Takes A Young Girl" is a bittersweet song highlighting the fact that as men age, they tend to lose the ability to appreciate and enjoy life's simple pleasures. The song suggests that the solution to this problem lies in the companionship of a young girl who not only makes the old man smile but also makes him feel alive again. The lyrics emphasize the stark contrast between youth and old age and how a young girl can bridge the gap between them.
Although the song's meaning may seem straightforward, there are deeper connotations behind the lyrics. The first stanza makes it clear that an old man's happiness is dependent on the presence of a young girl. The second stanza suggests that the old man has tried to forget his past but has been unsuccessful in doing so. The line "first she's yours and then she's his" implies that the young girl is just a temporary distraction for the old man and she will eventually move on to someone else.
The overall message seems to be that life is fleeting, and we should cherish the moments we have, particularly the ones spent with loved ones. However, it also highlights the fact that time waits for no one and aging is an inevitable part of life. But even in our old age, we can find joy and companionship with the younger generation.
Line by Line Meaning
It takes a young girl to make an old man smile
An old man needs the charm and energy of a young girl to bring a smile upon his face.
It takes a young girl to make an old man fly
A young girl can make an old man feel alive and youthful again like he can conquer anything.
Why should it take a young girl
To move this old heart of mine ?
The singer is questioning why it's only the youthfulness of a girl that stirs his heart instead of anything else.
It would take an old man too long to explain
How a young girl plays an old, old game
Trying to explain the mysterious game young girls play with older men is pointless because it takes too long to express and no one would understand the allure.
But that's just how it is, first she's yours and then she's his
And that's always, always the same.
Young girls always end up leaving the older men they have captured in their game for someone closer to their age, as this is the usual pattern.
It's been ten long years since I've cried
It's been five, I know five since I've even tried
Now why should it take a young girl
To move this old heart of mine ?
The singer reveals how long it has been since he's felt anything emotional and how surprising it is that it takes a young girl to stir such emotions in him.
Contributed by Eli L. Suggest a correction in the comments below.