Appreciating Jesse Winchester

A Troubadour’s Bout of Trouble: Jesse Winchester’s Final Album

(An appreciation of his career by Steve Satullo, June 2015)


“Ev’ry day, ev’ry day I get the blues

Ev’ry day, ev’ry day I get the blues

And anybody laughing, he ain’t heard the news

—Jesse Winchester


The sad news, if you haven’t heard, is that a sweet songbird voice has been stilled.  Jesse Winchester passed away last year, but left a moving final legacy in his posthumously-released album, A Reasonable Amount of Trouble, written and recorded between the bout of cancer he beat and the one that beat him.  What a gift it is, full of wisdom and warmth, as well as the harmony of his voice, his words, and his music.  Saturated with mortality, the album retains all of his wit and spirit – a perfect summation of a minstrel career.


Yes, he was a minstrel, a vagabond poet and singer, and a bit of a clown, but also a minister of sorts, dispensing hard-earned life wisdom in an amusing manner, succinct but many-leveled.  So this album turns out to be not just beautiful, but beatific — blessedly meek and mournful, merciful and pure of heart.


I’m a dedicated fan, hardly an objective observer, so let me defer to Jon Pareles, music critic of the New York Times:  “The songs have the gentle country lilt he perfected, sometimes going for swing or boogie, often easing into a cozy ballad. There’s a little extra huskiness in his maple-cured tenor, but no sense of strain or disappointment; he’s leisurely, thoughtful, amiable as always. Yet in their self-effacing way, his last songs reach deeper… The wry wistfulness of Mr. Winchester’s final statement is more moving than any self-pity could be.”


To let Jesse’s presence and essence linger with me a little longer, I set out to revisit his career and talk about the entire body of work within the context of his concluding album, meanwhile relating my life-spanning relationship with his words and music.


A Reasonable Amount of Trouble owes much of its shape and sound to Mac McAnally, who produced it lovingly as a tribute to his friend.  As Mac says, “If you know his work, you know there’s always some pathos and always some humor and always some real life in any Jesse Winchester song. That’s why he’s one of my heroes. He can make you laugh and cry in the same song.”  The production of this album sums up those aspects of Jesse’s work, nicely mixing death-haunted lyrics with pure fun.  I’ll start with the borrowed-time songs and finish with the good-time songs.


(You can freely read the full lyrics, and stream audio, for each of Jesse’s songs at his memorial website: .)


The opening song, “All That We Have Is Now,” sets the theme and tone for the rest, a jaunty celebration, with bluegrass-y riffs, of the all-too-brief passage of time.


Oh my my, look at the time fly

Sorry I really have to run

Oh I just love being with you

Really the whole thing was such fun

The sun is going down

There’s shadows all around 

And I feel more than wine

We must do this again sometime

But I can’t tell you when

But what a joy it’s been

All that we have is now


The repetition of the song’s buoyant assertion of the present moment is balanced by a wistful coda:


Well I wanted more somehow

But all that we have is now

That’s it

Baby all that we have is now


Presence is joy, but evanescence is pain.  Jesse’s method is self-defined in the lyrics, “laugh to hide the fear / and cry a perfect tear.”


This mingling of joy and regret is the overriding theme of this album and “Neither Here Nor There,” swinging like a velvet pendulum, announces the intent:


Let’s have a drink, let’s have a song

How about so wrong for so long


Jesse admits to making the whole thing up, the part about loving someone else “when I could only love myself.”  Unstinting in his self-analysis, he advises:


Just a word of warning

I’m so blind

I just go by feeling

Almost all the time


In his typical conflation of romantic break-up with all of life’s sorrows and disappointments, he finds a difficult consolation:


Well I’m so glad that’s all done

Although the ending’s never fun

My lord you should have seen the tears

Like they’d been building up for years

You see a happy man today

Although some blues don’t go away


In the refrain, he explains his modus operandi, and rejects self-pity:


And I played for the favors

And I worried the neighbors

And I don’t expect you to care

This is neither here nor there

This is neither here nor there


The concluding repetition doubles the meaning; not only is he saying that his sorrows are no concern of yours, he’s defining his state of being, neither among the living nor the dead, but some in-between condition.


Jesse gets deeper into his very personal regrets and reflections in “Ghosts,” in a pared-down, calypso-inflected arrangement that features his voice backed mainly by a strummed guitar and bongos.


And when I look back on those old times

It always makes me blue

And there are days where that’s all that I do


And oh, oh, oh these old memories can sure get me down

Going through life with these ghosts all around

And oh how they haunt me

They moan and they cry

Oh but I wish these ghosts would die


Implicit is the reverse wish, not only that his ghosts should paradoxically die, but that he should miraculously live.  He regrets lost loves, lost opportunities, and finally lost youth:


If you really need to reach me

Go to nineteen sixty three

Playing guitar by the radio

Anything in G

And when I listen to those old songs

It always makes me blue

And there are days where that’s all that I do


This reference to “those old songs” pays off handsomely in the inclusion of three of them on the album, which we’ll get to later.


The theme of sadness and regret is extended in “Everyday I Get the Blues,” in which Jesse frankly acknowledges, in a slow-groove whisper:


And I expect tomorrow one more little sorrow

Nothing I can’t pray my way through

Oh but every day, every day, every day I get the blues


He knows his personal sorrows are just that, merely personal, but they cloud his view of the light, and tears obscure his sight:


Oh I know the sun is shining

But it sure feels like rain

I agree the sun is shining

But I still say it feels like rain

I know the clouds are gone

But they’ll be back again.


Substitute “cancer” for “clouds” and you’ll be crying too.  If you’re anything like me, you’ll also be crying at the end of the last song on the album, Jesse’s final word, as it were.


Just So Much” was fittingly nominated for a Grammy as “Best American Roots Song,” and perfectly sums up the album’s commingling of sorrow and celebration in the face of life and death.


Singing in a hushed voice to strummed guitar, with subtle keyboard harmonies adding a hymn-like feel, Jesse begins with praise for the Lord’s flair with rainbows and sunsets, the sheer beauty of the world, then acknowledges,


There is this one place his power fails

He can help no one who won’t help themselves


Then comes an ironical assertion of the Panglossian principle that this is the best of all possible worlds:


Look at creation, it’s far and away

The best creation we have today


A further affirmation lands with a crushing kicker for someone on the verge of death:


Look at that starlight, just drink it in

You won’t see starlight like that again


Bringing the celestial back down to the personal:


He made the Heavens, he made the rules

Yet he can’t stop me playing the fool

Cause there is just so much

There is only so much

Just so much that the Lord can do


Jesse frequently self-identifies as a “fool” but to me he is some kind of holy fool.  He then delivers his plangent final meditation, his ultimate words of wisdom, on the meaning of life and death:


So where do I find Him

It’s never quite clear

I’m dying to find Him

But dying’s my fear

Is there perfection

Will there be pain

Will I see Momma and Daddy again

Why won’t He tell me

What it’s about

Give me some answers

Clear up my doubt


The only answer, however, comes in the refrain:


But there is just so much

There is only so much

Just so much that the Lord can do

It’s true, too true.


Trust Jesse to end it all with truth.  With the hard truth of death, in spite of beauty and meaning, in defiance of our hopes and wishes, as the culmination of all our joys and regrets.


You can see why these songs don’t appear in sequence on the album – it would be an emotional bludgeoning that few could take.  So let’s look at the lively fun that leavens the whole.


She Makes It Easy Now” is a joyful story, powered by locomotive rhythm and twanging guitar, of a bad boy turned into a good man by the love of a woman:


Well she cleaned him up

And she calmed him down

And she set him back on solid ground

And he’s “yes dear, no dear” the live long day

But believe it or not he likes it that way-ay-ay


Meanwhile “Never Forget to Boogie” is the bad boy’s unrepentant anthem, in an all-out rock-solid groove:


You said you’re sorry, you said we’re through

You said I’m good for nothing

But honey that’s what I do

But I never forget, I never forget

I never forget to boogie

It’s uppermost in my mind


A Little Louisiana” is a Cajun romp, celebrating the “Loose-iana” you want to carry with you everywhere, as an antidote to care and disappointment.  Given Jesse’s birthplace, you have to assume Lousiana includes the love of “Momma and Daddy,” as well as the Mardi Gras spirit:


Well who knows what lies around the bend

It could be good but then again

It could be empty cold and bare

Like I say you better be prepared

Take a little Louisiana

Take a little Louisiana

Take a little Louisiana with you everywhere you go


Don’t Be Shy” is another jeu d’esprit, apparently in the setting of adjacent honkytonk barstools, with swinging country accompaniment.  It seems as though it should be sung by a woman, but in the voice of a 68-year-old man it takes on a delicious irony:


Oh I can tell your Mama raised you right

You’re sitting there so perfect and polite

Is it gonna take another glass of wine

Before I learn what’s really on your mind


Can you see the grey-bearded, cancer-ridden geezer leaning in for the score, in the throes of pure projection?


Do you find me peachy keen, oh yeah

Are my eyes the nicest eyes you’ve ever seen

Am I wooable, am I doable, ice cream and pecan pie

Well then say so, don’t be shy


Ever hopeful, even unto death:


Oh do I strike that match and light that little fire

Do you hear my name and feel a rush of pure desire

If you want me to hug on you so bad that you could cry

Well say so, don’t be shy


Likewise, context gives new layers of meaning to the oldies Jesse covers on this album.  “Rhythm of the Rain” is not just a great old song, sung beautifully, but a perfect fit for this album:


Listen to the rhythm of the falling rain

Telling me just what a fool I’ve been

I wish that it would go and let me cry in vain

And let me be alone again


But what really makes the song worthy of inclusion is the pure Southern lilt of Jesse’s “pitta-patta pitta-patta.”


Devil or Angel” — in full period production, with backing vocals and a great back and forth between Jesse’s voice and a saxophone — adds up to another role reversal.  The singer wonders whether his girl is a devil or angel, but Jesse seems to be asking the same question of himself:  “Devil or angel, I can’t make up my mind, which one [I am] I’d like to wake up and find.”   He finally settles on a note of acceptance, “dear whichever you are, I love you.”


The doo-wop of “Whispering Bells” is less thematic, but provides a blessed relief between two extremely dark, sad songs, and recalls such Jesse originals as “Sham-A-Ling-Dong-Ding.”


Fool, jester, minstrel.  Sage, seer, minister of the gospel.  Lover, loser, living loose.  Go, listen, hear for yourself.


* * * * *


Jesse played all of these roles throughout his long career, as well as in his last studio album.  Now we’ll take a lengthy excursion through that career, as it provided the soundtrack of my own life.  I never knew Jesse personally, but he clearly knew me, knew just what was going on in my life at any given time – how else could he have written songs that spoke to me so directly, while speaking so generally to the human condition?


(While talking about the final album, I’ve tried in my inexpert way to give some sense of the sound of each song.  For the rest, I will approach Jesse mainly as a lyricist, giving priority to his words, and less emphasis to his singing, playing, and all-round musicianship.  I merely point to the variety of his sounds – folk, blues, country, gospel — and will link to each album on his memorial website, so you can hear the songs for yourself.)


Back around 1970, it was probably a Rolling Stone review of his first, self-titled album that connected me with Jesse Winchester.  That, and Robbie Robertson’s involvement as producer, at a time when I was a big fan of The Band.  I was attending Williams College, having returned after dropping out and then getting married, but living in a trailer park next to the race track up in Pownal, Vermont, just across the border from Massachusetts.  I finally tracked down a copy of the album at the Harvard Coop.


On the cover it had a stark frontal portrait of a bearded Jesse staring into the camera, in front of a rough-hewn log-cabin wall, like a Walker Evans photograph of an Appalachian sharecropper.  I took it home, and put needle to vinyl.


Whoa – immediate connection!  I loved getting “drunk and nasty” on the hard-rocking “Payday” as much as the gospel shout of “Quiet About It.”  The latter was the title song of a tribute album of Jesse songs covered by famous artists, which was released after his first bout of cancer.


Be of good cheer

It’s all in His plan

He’s walking with us

And He speaks through every man


But I have this notion

Call it my fear

That I will die alone

And even He won’t be there


But when I feel that way

I thirst, and I want to shout it

Trust me Lord, to be quiet about it


This first album follows Jesse’s story from the ocean-wading boy of “Biloxi” to the Canadian exile of “Snow.”  From the lying-awake-at-night rumination on guilt and depression in “Black Dog,” to pursuing girls in “Rosy Shy” and “That’s a Touch I Like,” and leaving girls in “Skip Rope Song” and “Brand New Tennessee Waltz.”


Above all, there was “Yankee Lady,” still probably Jesse’s best-known song.  At the time, in point of fact:


I lived with the decent folks

In the hills of old Vermont

Where what you do all day

Depends on what you want


And there was indeed a woman who “rose each morning and went to work” and “kept me with her pay.”  Jesse left his, when “there was winter in the breeze,” but I stayed with mine, to this very day.  She still “reminds me of my worth.”


Jesse’s second album, Third Down, 110 to Go, came out in 1972.  This cover had Jesse in profile, with a smile on his face and his beard better groomed.  The title alluded indirectly to his Canadian exile, since it represents the most desperate situation on a football field north of the border.  It’s about finding hope in a hopeless situation.


This record was slower to grow on me, but soon became my favorite.  I’d graduated from from Williams, but stayed in Williamstown working at the College Library.  I was living near the center of campus in the house of a professor on sabbatical, who happened to have an admirable audio system, and I cranked it up to play this album.


A young philosophy prof was walking by and couldn’t help but hear.  He stopped at my open door to ask if I knew that the singer was a Williams alumnus, from his own Class of 1966.  I was already a big fan of Jesse, but this alma mater connection turned me into a lifelong follower, with the intimacy of a secret sharer.


These days the Internet adds many further levels of intimacy, and through what follows I will freely access facts about Jesse’s biography that I could at the time only intuit through his music.  Again, I want to give credit to his memorial site for providing such a treasure trove of material.


So now I know how the lad from Down South wound up in the northwest corner of Massachusetts.  How he was born on a military base in Louisiana during WWII; how his father used his veteran’s benefits to buy a farm in Mississippi to play out a back-to-the-land dream; how Dad eventually returned to the family home and legal business in Memphis, where Jesse spent his teen years.


Besides lawyers, there were preachers in his family, including the great-grandfather for whom he was named, an Episcopal bishop.  But since his mother was Catholic, that’s how he was raised.  An uncle led him to Williams, where he figured he got in on a Southern exemption:  “I really had to struggle to keep up with those Northern boys.”


He majored in German, primarily to take a junior year abroad in Germany, where he studied mainly in clubs, playing with a band in the same sort of venues that the Beatles came out of a few years before.  That immersion in another culture and language made it easier for him to do something similar shortly after graduation, when he got his draft notice and chose to get on a plane from Memphis to Montreal, with a guitar and a few hundred bucks in his pocket.


So we’re back to Canada and Third Down, which commemorates his becoming a citizen of the Great North.  “Isn’t That So” leads the way and sets the tone of angelic deviltry (or devilish angelicism) that marks so much of Jesse’s work.


Didn’t He know what He was doin’

Putting eyes into my head?

If He didn’t want me watching women

He’d a-left my eyeballs dead


Isn’t that so?  And doesn’t the same apply to the fruit of the vine?  “His own son got a reputation / turning water into wine.”  Isn’t that so?  “You’ve got to go where your heart says go.”  Isn’t that so?  Then in a verse that became one of my anthems:


Line of least resistance lead me on, lead me on

Line of least resistance lead me on


The next song, “Dangerous Fun” also dispenses good advice, in the face of a resistant lover:  “It takes patience to walk on / And spirit to run / And nothing to pity yourself / But it’s dangerous fun.”


Jesse continues in preacher-man mode with “North Star”:  “Heaven’s got this one star that don’t move none / And that’s the place you want to aim your soul.”  In a bouncy verse that convinced me that Jesse must have read Eliade at Williams, like me, and developed his own theory of the omphalos, axis mundi, and the navel of the world:


Now does the world have a belly button?

I can’t get this out of my head

Because if it turns up in my yard

I’ll tickle it so hard

Till the whole world will laugh to wake the dead


Jesse is again in ambiguous imperative mode in “Do It”: “Do it / Till you’re sick of it / Do it till you can’t do it no more.”  Whether Sisyphean persistence or addictive overindulgence, it comes out the same.  But another line from this song entered the ranks of my maxims for living:  “If we’re treading on thin ice, then we might as well dance.”


Further songs give the good advice to “Let love come the easy way,” and “To mourn the night / We’ll glorify the day.”  Some talk of touring and performing, “Midnight Bus” and “God’s Own Jukebox.”  And others give hints of home life, the instrumental “Lullaby for the First Born” and “Do La Lay”:


Oh I am your father now

I can’t get out of that

You are my child now

You can’t get out of that


He promises the “little child of love” not to get in his way, but just to look out from above, over where the baby “do la lay.”  The song “Silly Heart” may refer to the baby’s mother, with “silly” certainly taking its original connotation of “innocent,” in the dual meaning of “I wish I had a silly heart like you.”


Two years later, Learn to Love It came out, with a jacket photo that showed a smiling Jesse holding a baby.  During a period of transition in my own life, moving from the bucolic Berkshires to the Big Apple, I wasn’t keeping up with new music, but started to hear Jesse occasionally on the radio in the car.  I belatedly got this record as a Christmas present in 1976, and it didn’t take me long to learn to love it.


The album starts with “Wake Me,” another gospel shout:


Come on and wake me wake me wake me Lord

Turn my head around

Shake me shake me shake me Lord

Thunder be the sound — oh oh


“Every Word You Say” is yet another song that means so much to me, so simply stated and yet so true to my own beliefs and practice:


I’m no good company

I guess that’s true

I like my silence

Like I love you

But if you feel like talking, talk away

I’m going to hang on every word you say


The next song asks the question “How Far to the Horizon” – “I know it’s pretty country / It borders on the sky / It’s nothing but my faith that says / I’ll be there by and by.”  In the face of expectation, millennial and personal, all we can do is pray, “Just a few more miles to the blue horizon / Oh love don’t give up on me.”  (Printed lyrics say “Lord,” but I’m certain Jesse sings “love,” a much more encompassing idea.)


Two songs in French reference Jesse’s reverse Acadian journey, “L’aire de la Lousiane” and “Laisse le bons temps rouler.”  Let the Cajun good times roll, indeed.  And two others explain the journey north:


Cause in the year of nineteen and sixty-seven

As a somewhat younger man

The call to bloody glory came

And I would not raise my hand

Cause I’m baptized by water

So I’ll pass on the one by fire

If you want to fight

Go on and fight if that be your desire


That’s from “Tell Me Why You Like Roosevelt” – “he’s the poor man’s friend” — and then “Pharoah’s Army” thanks God for the little Hebrew children that got away and “lived to tell their story and fight another day.”


“Defying Gravity” was of course something Jesse did till his dying day:


I live on a big round ball

I never do dream I may fall

But even one day if I do

Well, I’ll jump off and smile back at you


He’s heard that we’re circling a star, and thinks, “I’m dizzy so it may be so.”  Defying the gravity of the situation, that “the high must lay low,” he concludes, “when I do fall I’ll be glad to go.”  (In one later interview, he admits that cheerfulness in the face of death “seems like a lot of BS,” casting ironic doubt on his own most soulful affirmations.)


Jesse may sometimes long for his soul to have its rest, to find its way back home, and taste again the sweet magnolia wine, but he knows, “The End is Not in Sight.”  The album ends with the pulpit testimony, “I Can’t Stand Up Alone”:


Ah you can’t stand up

All by yourself

You can’t stand up alone

You need the touch of a mighty hand

You can’t stand up alone


All this meant a lot to me, but became positively oracular with “Mississippi, You’re On My Mind,” perhaps Jesse’s second most famous song.  Because Mississippi was very much on my mind at the time, since I’d become deeply involved in correspondence with a woman who lived down there.  He was remembering, with sensual and revelatory clarity, his boyhood past on that Mississippi farm, but for me that song betokened a more future-oriented longing.  Again the lady in question is with me to this day, long since having moved from Mississippi to Massachusetts, and become the mother of my son, as well as business and domestic partner.


Enchanted all over again, I ran out and purchased Jesse’s 1976 album, Let the Rough Side Drag— this cover featuring a young boy in a rocking chair, faced away from the camera – to revive and extend my connection to him.


The title song leads the album, in which Jesse enumerates and celebrates all the good things “the Lord has done,” from “cows don’t fly” to “making love is fun.”  Above all, “What a good thing to make a joyful noise.”  So when things ain’t so great, “Let the rough side drag / Let the smooth side show / While you drag your load / Everywhere you go.”


“Damned If You Do” is an answer to the liars and rascals “who will tell you that love’s a pointless game to play.”  Jesse advises lovers “to take the love you want / Cause you’ll be damned if you do / And damned if you don’t.”


“Step by Step” is how “All the happy saints go marching in,” though “Jacob’s golden ladder / Gets slippery at the top / And many a happy-go-lucky saint / Has made that long, long drop.”  In a gospel rhythm inflected by the blues-y wail of a mouth harp, Jesse expresses his ambivalence about the march to sainthood:


If I’m late don’t wait

Go on without me

I may tarry a while

Cause I need to know

Before I go

How come the devil smiles


(In a perfect wedding of my all-time favorites, this song accompanies the concluding montage of the first season of The Wire.)


“Lay Down Your Burden” is Jesse’s response to a lover or child who has found out that “It’s a cold old world / That we’re walking through,” or discovered “the fine fine line betwixt love and hate.”  He pleads:


Lay down the burden of your heart

I know you’ll never miss it

Oh show your daddy where it hurts

And let your daddy kiss it


“Everybody Knows But Me” is a spirited comic take on the theme of “I Heard It Through the Grapevine,” in which Jesse gets to pronounce repeatedly “I’m a fool,” as the realization grows that everybody knows but him.


“Blow On Chilly Wind” defines the love, both romantic and divine, that “gives a lamp to lead us through” and protects our necks from the chilly winds of life.


“Working in the Vineyard” may be hard and tedious labor, but it has its compensations, if we’re:


Working in the vineyard

In the Lord’s employ

Getting good and mellow

On His wine of joy


“It Takes More Than a Hammer and Nails” gives good advice on what makes a house a home:  “It takes a firm foundation built on faith and love,” also “truth and trust”:


Show your neighbor what a friend is for

With an open heart and an open door


“As Soon as I Get on My Feet” is when the wistful, plaintive singer will return his girl’s “love so sweet,” when he turns from boy to man, “so wise so strong,” working “so hard the whole day long.”  Making a virtue out of weakness, he can’t grow up alone.


“Maybe life is just put on for show,” but it’s “The Only Show in Town,” don’t cost a nickel to get in “but you’ll pay dear to hang around.”  So:


Maybe love’s a joke you’ve heard before

Still it makes you laugh until you cry

Laugh until you’re rolling on the floor

Till the tears are streaming from your eyes


It’s clear that Jesse finds parting such sweet sorrow since he returns to it again and again, memorably in reprising “The Brand New Tennessee Waltz.”  Looking back on his home and the girl he left behind, he repeats his history, “too sad to be true”:


But I left Tennessee in a hurry dear

The same way I’m leaving you

Because love is mainly just memories

And everyone’s got him a few

So when I’m gone I’ll be glad to love you


With this album, I yet again felt that Jesse was speaking directly to me, expressing my life in his words, so I decided to talk back to him.  I wrote him a long letter full of mixed motives.  I wanted to tell of the personal connection I felt to his music, but also had a proposition to make.  With incoming President Jimmy Carter’s promise to pardon Vietnam draft resisters who had gone to Canada, the way was open for Jesse to perform in the U.S., and I thought an article about his return might be a piece of freelance writing that I could actually sell.


Did the letter ever reach him?  I never received any response, and in retrospect can easily understand why, but almost forty years later, I feel as though I am finally writing the profile I imagined back then.


Taking advantage of the touring opportunities now open to him, Jesse released another album in 1977, Nothing But a BreezeWith his life taking a turn, the cover photo is a tight shot of Jesse laughing, but with his hand over his face, he might also be wincing and saying something like “oh, my aching head.”


The title song lays out the situation clearly:


Life is much too short for some folks

For other folks it just drags on

Some folks like the taste of smokey whiskey

Others figure tea’s too strong

I’m the type of guy who wants to ride the middle

I don’t like this bouncing back and forth

Me, I want to live with my feet in Dixie

And my head in the cool blue North


And there we’ll do just as we please

It ain’t nothing but a breeze


At the time, I was torn between writing and filmmaking as career possibilities, even though neither would ever make a living for me.  Having just obtained a Sony PortaPak, the first personal video system, I made one of my early efforts a prototype music video of three songs from this album, each composed of one song-length shot.


“My Song Bird” started with the needle descending on the spinning record, and roamed around our well-windowed fourth-floor corner apartment in Park Slope, looking down at the tree-lined block leading to Prospect Park, with a sliver of a view of the World Trade Towers in the distance, and planes flying overhead.  I tracked around the room to my desk, where a blank legal pad lay with a capped pen across it, to the floor pillows where my copy of Dickens’ Hard Times was splayed open, and over to our German Shepherd Emma lying there peacefully — “she shall be my prisoner her life long.”


My songbird wants her freedom

Don’t you think I know?

But I can’t find it in myself

To let my songbird go


In a time of writer’s block, I shared Jesse’s prayer:


O Lord, when your jeweler’s eye

Peers into my soul

O Lord, I am overcome with shame

Take me, Lord, and purify

Heal me with a word

Lord, I beg a gift I dare not claim


For “Twigs and Seeds,” I set the video camera on a tripod pointed at my desk, and sang along while rolling a joint, celebrating times of plenty with a song about well-known scarcity.  Though I was not “fresh out of that herb that’s so dear to me,” I wailed along:


There’s nothing but twigs and seeds

Twigs and seeds

And they sure don’t deliver the punch

That this old head needs


For “Rhumba Man,” I left the camera on the tripod, and frolicked in a way I would never do in public, to create a dithyrambic record of that most rare sighting, me dancing without inhibition to the irrepressible rhythm:


There’s lots of guys on the floor tonight

With a lot slicker steps than me

My step might be old fashioned

But that’s just fine with me

I got a couple of rhumba steps

You might like to see


Putting all my usual embarrassment aside, I could boastfully sing along, “If I were you / I’d hang on to / a rhumba man like me.”


As often, Jesse is at his most personal when appropriating the words of other songwriters.  In “Seems Like Only Yesterday,” he’ll “never forget that dreadful day / when I decided to run away … much too young to realize / that I’d regret it all by and by.”  Now he wants to accept the “whole lot of love in that old house,” which he threw away because he “was just too young and blind to see.”  The exile yearns for the family he left behind so abruptly.


A similar yearning for his old home Down South comes through in “Bowling Green,” where “a man down in Kentucky sure is lucky.”  One infers a certain romantic disappointment from the selection of “It Takes a Young Girl,” which is confirmed with Jesse’s own songs, “You Remember Me” and “Gilding the Lily.”  One song bitterly confronts an old love with memories of “the funny way I sit there / when someone says good-bye” while he still recalls “what a child you are underneath it all.”  The other laments, “O all of my gifts pale as I give them to you.”  Even his characteristic Cajun tune in French translates to “Why Don’t You Love Me?”


Varieties of heartbreak would be central to his next album, but in the interval we were both on the move, Jesse able to tour in the U.S. for the first time, and I moving from New York back to the Berkshires.  Our paths crossed in a concert at Tanglewood on Labor Day weekend in 1977, where Jesse appeared on a bill with Randy Newman and Emmylou Harris, a fantastic grouping that was matched by the sextet with which I attended, including my oldest, newest, and closest friends, gathered from Vermont, Mississippi, and my hometown of Cleveland.  Definitely a concert to remember.


Luckily for us old folks, we don’t have to remember anymore, but just look things up on the Internet — where I soon found this review from Rolling Stone:  “Most striking about the concert (which lasted about five hours) was the audience’s tremendous passion for Jesse Winchester.  Jesse was in pure and fine voice, and both he and his Canadian band were far more relaxed and rehearsed than they had been during the initial leg of their first U.S. tour.”  Ovations greeted many songs, but “Yankee Lady provoked the greatest demonstration of all… At the song’s end, the audience stood for nearly five minutes and applauded: for his flight to Canada, his return, and the fact that he was even more affecting in person than on record.”


The next year, A Touch on the Rainy Side came out, and to tell the truth, it was Jesse’s album that registered least on me, had the least connection with my own life, except for a few songs that made it onto best-of compilations or live recordings.  Turns out Jesse was dealing with marital and drinking problems, as well as returning to the States to perform, giving me little to identify with.  The cover shows him in a chair looking mournfully askance at the camera, with a bare broken-down room in the background.


Several songs seem to be directly addressed to the wife he was losing at the time.  The title song pleads with his “sunshine” not to hide, just because he is “A Touch on the Rainy Side.”  Later he sings of his “Wintry Feeling.”  “Just Now It Feels Right” seems like another can-this-marriage-be-saved? moment.  Other women are yearned for in “Sassy” and “Holly,” and his cover of “Candida” could be addressed to wife or other.  “High Ball” and “Little Glass of Wine” speak to his urge for flight and dissipation.


But two songs stand out on this album, pulling in opposite directions.  “The Showman’s Life” portrays the downside of his expanded opportunities for performing:


A showman’s life is a smoky bar

And the fevered chase of a tiny star

It’s a hotel room and a lonely wife

From what I’ve seen of a showman’s life


And then the repeated refrain:


Nobody told me about this part

They told me all about the pretty girls, and the wine,

And the money, and the good times

No mention of all the wear and tear

On an old honky-tonker’s heart


The album ends, however, on a desperate upbeat, in full gospel mode, with the imploring repetition, “I’m Looking for a Miracle”:


Now Thomas was a doubter, he would not understand

He would not believe until he touched it with his hand

Now I’m ashamed to say it, but he’s lot like me

I want to believe, Lord, but first I want to see


Despite a religious upbringing and lots of god-talk in his songs, Jesse was not a church-goer or a member of any denomination, more skeptic than believer.  He liked to quote Peter Ustinov:  “We are divided by our beliefs, but we are united by our doubts.”


A few years passed till Talk Memphis came out in 1981, a return to Jesse’s roots and his form, apparently after his marital break-up.  The “Leslie” of the earlier album is addressed directly:


Leslie, I got it now

It all comes easy, once you show me how

One thing mystifies

I know you love me, but I don’t know why


But clearly there’s been a split, and a reconciliation to the fact of it, despite regret and continued love.  “If Only” voices the regret, but “Let Go” is still the prescription, even though “I Love You No End,” and the ex-wife can “Reckon on Me.”


“If Only” imagines living on the ocean floor, far from the storm and roar, even if we’re in “in a great big tear.”  And even if “the blues always find you”:


Oh the garden’s here if we only knew

Oh the door is so wide we could breeze on through

We could soothe our souls, we could understand

See the lion lay down by the lamb

But we linger on by the garden door

Boy the old world hurts but we still want more


But the refrain explains the only way to confront the lacrimae rerum:


Oh I, I just wonder where would I

Be without the tears I’ve cried

Unless you’re from another star

Tears are part of what we are


So the next song answers:


And oh Lord help me let go

I can’t keep her I know

It is now and ever was so

If I want to hold her I’d better let go

Better let go, better let go, better let go


That repetition doubles down in another song, as Jesse recalls the birth of their love and the good times they had, and assures her “you still have your old place in my heart”:


I love you no end no end

I love you no end

I just go round and around

I love you no end


In the end, after being the “man of your dreams and your very bad boy,” Jesse implores his lost love to “reckon me true.”


The multiple meanings of “reckon” include — I reckon — a measure of the Southern talk that he celebrates in “Talk Memphis”:


Listen to you move your mouth

I bet you come from way down South

Please don’t tell me, let me guess

You’re from the town that I love best


Longing for the city high on the bluff, he pleads:


I swear I can’t get enough

Listening to you talk that stuff

Talk Memphis, oh yeah, talk Memphis


Several other songs embrace the rockabilly heritage of his home town.  “Say What” was his top-charting song ever, about taking a break from depressing news:


The daily grind is getting me frantic

I see myself as a laid back romantic

So, oh, what you say if

We just let it slide for a day girl

What you say?


“Hoot and Holler” and “Sure Enough” offer some relief in the same Southern vernacular:


Ah sometimes it’s hard to follow

How some folks will give a dollar

Just to hear me hoot and holler

About how I love you, oh I do


It’s “like getting paid for eating candy,” but sure enough,


Now it’s too late to fix my heart

It’s too late to mend it

It’s too late to save my soul

So come on help me spend it

Yeah, yeah, yeah, it’s a little bit old, that’s right

Yeah, yeah, yeah, but it’s good as gold


Surely, that’s the way to move on from heartbreak.  But seven years would pass till Jesse released another album.  Humour Me came out in 1988, with the defiant Canadian spelling, and a picture of Jesse standing casually, with his hands in his pockets, hair and beard well-groomed, wearing a cardigan and staring at the camera with a wary look that seems to say, “This is just me, eh?”


I was definitely inclined to humor him.  Even though his advice was to “pay no mind if I were you,” I paid total attention, listening over and over again as I worked late into the night at my own small business, Either/Or Bookstore, absorbing his words into my soul.


Jesse was addressing a girl in chanting “I Want to Mean Something to You,” but there’s no question that he meant something to me:


Our paths cross every day, but they never meet

Now my imagination says it would be so sweet

But I don’t want your casual love, no, that’s too cold

Girl I want to open your heart

And just reach in, and just take a hold


I’m no girl, Jesse, but consider that mission accomplished.  Among the many things that this album in particular meant to me was the hold he had on my imagination.  So polished in lyrics and production, it mined the usual subjects of the American popular song – wanting a girl, losing a girl – in a variety of styles, from doo-wop to country.


Heartbreak remains the keynote.  “You Don’t Love Me Anymore” takes a wry approach:


Lately I’ve been thinking dear

And this is not like me

I’m good at being blind to things

That I don’t want to see

Now you don’t seem so cuddly with me

Like you were before

Gee, I don’t think you love me anymore


Like Jesse, like most of us I imagine, I too am “good at being blind to things that I don’t want to see.”  This is one of many instances when Jesse’s honesty about himself helps me to understand myself, to see universal traits in particular characters.


“Too Weak to Say Goodbye” addresses the same situation:


Still even though the feeling’s gone

Still there’s something lingers on

Strong enough to make me cry

But still too weak to say good-bye


On the other hand there’s still the hankering after women, like the cutie called “Well-a-Wiggy” (successor to Sassy and Holly) and the weepy “Willow,” but overall this is an album of ironic reversals.


“If I Were Free,” I’d chain myself to you and throw away the key.  “They Just Can’t Help Themselves,” so they help themselves to whatever they want:


And they just can’t help themselves

They’ve give up control

They hear a little voice

That lives down in their soul

Say let’s us go and find a cozy little hell

And no one tells them no

And they just can’t help themselves


There’s only one answer to these common but various problems of addiction:


It’s good when a game’s running smoothly

And it seems like it always goes well

For those who can take it or leave it alone

But God help them, if they can’t help themselves


“Let’s Make a Baby King” is the biggest reversal of all:


We need a revolution

The whole world’s upside down

We need a new direction

We got to turn this whole thing around

We need a lord to guide us

And teach us wrong and right

We need a lamb to lead us, into a land of light


So once upon a Christmas morning, Mary felt sadness mingling with the joy when the angels sang:


Let’s make a baby king

Let’s make him lord of all

Let’s give him everything

Let’s make a baby king


Though I had children of my own by this time, Christmas mostly meant to me, as a retailer, the brutal slog of the busiest season of the year.  Even before that, my studies in the biblical tradition had confirmed the Nativity as the most made-up-after-the-fact part of the New Testament, so I never ascribed any spiritual significance to it.  But this song gave me a whole new perspective on, and appreciation of, the story.


Must have done something for Jesse too, since “Thanks to You” seems to be addressed to God.  He feels like a baby boy floating in the blue, might take credit for the goodness, but knows it’s “thanks to you”:


Oh yeah, I’m a sinner and I ain’t some beginner

I’ll uncork a pint of trouble

Then sit down and drink a double

I’m thirsty for something lighter

That’ll get me even tighter and tighter

Until one day I think I hear angels play


Along with Jesse, I take a good deal of consolation from the pie-in-the-sky idea:


Well, someday up in glory

I’ll weep and tell the story

To someone who will smile and say

“You’re a mess, but you’re my child”


Eleven years and a retirement from live performing would elapse before Jesse’s next album, Gentleman of LeisureAnd I was there waiting for him, something of a gentleman of leisure myself, my independent bookstore having bit the dust like so many others.  In his leisure, Jesse had honed his lyrics – and his persona – to a fine edge, and his musicianship remained impeccable.  This was his first album on CD, so it’s the one I’ve listened to — and identified with — the most since 1999.


The cover shows a Jesse grown older and gaunter, leaning on a post and looking at a newspaper, maybe the want ads, while casting an ironic glance at the camera.  In the background, as if in a subway station, a blur of busy women passes in the opposite direction.


Looked at from the perspective of his whole career, it’s easy to see how each song on this comeback album fits into one of his traditional categories, expresses his persistent themes — love and loss, escape and commitment, the boogie and the bogeyman, indulgence and transcendence.


“Club Manhattan” and “Sweet Little Shoe” kick off in party mode.  From there on, he philosophizes about love and laments loss, deals with defeats and aspirations, declares his independence and his dependencies, laughs and cries, dances and mourns.


The “Gentleman of Leisure” is looking for “a job that’s not too demanding,” with lots of perks and not much to do.  His only qualification:


Let me take my time

Bet you I can please you


Mr. Winchester, you’ve got the job!


In a similarly buoyant mood, Jesse celebrates hometown hero Elvis (and his Caddy) in “Just Like New.”  On the darker side, he acknowledges the “Evil Angel” who sits on one’s shoulder, and really knows its stuff:


First you start ’em with a little

Till they just can’t get enough


Whether its whiskey, cigarettes, or cheating love, the first one burnt your tongue or eyes or soul, but soon, “you, you had to go and find another.”


In “No Pride at All” and “I Wave Bye-Bye,” Jesse again has parting words for the departing lover, wishing her well despite all.


But if ever you’re caught in a corner

If ever your pride should lead to a fall

Bring it to me

I’ve got no pride at all


In another verse that became scripture to me:


I don’t hold a hurt

Like some people do

I say, what the hey

People get that way

I get that way too


And how’s this for the perfect send-off?


I wave bye-bye

I pray God speed

I wish lovely weather

More luck than you need

You’ll only sail in circles

So there’s no need to cry

No, I’ll see you again one day

And then I waved bye-bye


With Jesse, it’s rarely either/or, but generally both/and.  Happy and sad, yin and yang, devil and angel.  On the one hand, “you can’t hurt me like you do,” “Just Cause I’m in Love with You,” but on the other, “You Tickle Me.”  To the faithless lover:


But every time you hurt me I grow a little stronger

I’ll soon be strong enough to say goodbye


With the party girl who likes a good laugh more than good taste, Jesse has to warn:


Let’s get serious here a minute

And show me how real love can be

And then you can tickle me

Baby you tickle me

Oo whee, baby but you tickle me

Oo whee, baby but you tickle me


In “Freewheeler,” Jesse’s the man who can’t be tied down, and in “Sweet Loving Daddy” he’s the husband left behind by the straying wife. In the former, he’s got nothing and nobody and nowhere he’s got to be. Admits to riding roughshod over lovers, “taking trust, returning pain,” time and time again, the emptiness feeling good, with his only friend the wind.  But in the latter, he has to turn around, and ask again:


How could you have taken a downtown man

For a good loving daddy

A true loving daddy

A sweet loving daddy like me?


The two songs that sum up the wisdom of Jesse’s aging into his fifties are “That’s What Makes You Strong” and “Wander My Way Home.”  In the former, the strength of a syllogism leads to a paradox:


If you love somebody

Then that means you need somebody

And if you need somebody

That’s what makes you weak

But if you know you’re weak

And you know you need someone

O it’s a funny thing

That’s what makes you strong


If you trust someone, then you’re bound to be disappointed:


But if you’re the trusting kind

This don’t even cross your mind

O it’s a funny thing

That’s what makes you strong


With this power, “the meek come sit beside the king” —


That’s what lets us smile

In our final hour

That’s what moves our souls

And that’s what makes us sing


Jesse’s most important message is delivered twice, backed by a gospel quartet and reprised with a wicked guitar riff.  In this song, he asks directions from a man, a woman, and a child in turn, and they all have the same answer:


Go straight, you can’t miss it

But you’ve got a ways to go

If you get lost, mister, just keep moving

No matter what, you carry on

You may stumble into heaven

You may wander your way home


So Jesse was back to performing now, and when I heard he’d be appearing at the Iron Horse Saloon in Northampton, it was definitely worth a trip over the mountain to see him in person.  The setting proved to be amazingly intimate, so the Yankee Lady and I, along with our 14-year-old daughter, took a table within ten yards of where Jesse sat on his stool and spun out his stories, with only his guitar for accompaniment.  What he could do with just his voice and six strings!  His dulcet, soulful singing and nimble picking!  His accent and phrasing!  The sentiment and wit he could pack into a sigh or lip smack!  (For Jesse’s solo performance from this era, listen to Live from Mountain Stage.)


It was a magical night, the intimacy of the venue reinforcing my feeling of familiarity with Jesse, and at intermission someone at the next table leaned over, and commented, “Hat’s off.  I could never interest my teenage daughter in music like this.”  But that’s my girl, as sensible and sensitive as they come.


I would see Jesse in performance one more time, in 2004 at the Mahaiwe in Great Barrington, an old-fashioned movie theater restored into a performance venue.  We sat in one of the front rows, for another close look and listen, as the intimacy of his performance translated well into the larger space.  At the time, I didn’t know of his major transition a couple of years before, when he married Cindy, who must have talked Memphis to him, and returned to live in the U.S.


That probably inspired his next album, Love Filling Station, which came out in 2009, with a couple of old-fashioned gas pumps on the cover.  You know Jesse was re-filling his tank, as he boasts/complains in “Wear Me Out”:


Well I’m up in the morning

Scratchin and yawnin

My baby loves me all night long

You know how to please me

But please take it easy

Cause you know I’m not that strong


The album kicks off with an anthem to his new love, “O What a Thrill” – she makes the “stars stand still”:


O girl, any moment

I may kiss your lips

O it’s, it’s been a while

Since I felt like this


Though Jesse might be a patriarch by now, love makes him a teenager again, and doo-wop songs return him to the yearnings of youth, in ways that can bring a tear to the eye, as in “Sham-A-Ling-Dong-Ding”:


The boys were singing shing-a-ling

The summer night we met

You were tan and seventeen

O how could I forget

When every star from near and far

Was watching from above

Watching two teenagers fall in love


“Eulalie” is another object of high school longing:


Eulalie just loves attention

She’s a child in that respect

She’s a girl whose pretty looks

Have been a chain around her neck

Cause with all the boys who want her

Why she’ll never notice me

And I could really love you, Eulalie


If only you knew me like I know you, even watching from a distance, you’d see my love is sincere:


I wish I could show you

Hey look over here

Eulalie, Eulalie, Eulalie


But sometimes the boy on the sideline gets lucky, and then he has to say “Bless Your Foolish Heart”:


O every time we go downtown

The boys watch you walk by

You don’t see their eyes

But I bet you hear them sigh

The whole darn town’s in love with you

But here’s the funny part

That you love me, girl,

Bless your foolish heart


Though you could have had any boy in school — or any man, for that — “you chose the biggest fool”:


O you may be too good for me

But you can’t be too smart

Not if you love me, girl,

Bless your foolish heart


Jesse’s beautiful cover of “Stand By Me” shows where all this folderol ought to lead, but “It’s a Shame About Him” and “Loose Talk” tell stories, comic or poignant, of some stresses of married life.


The opposite side of the story is told in sequence: “I’m Gonna Miss You Girl” — “I Turn to My Guitar” — “Lonely for a While”.


After summer love at the lake:


O yellow autumn moon

You find me blue tonight

What with the summer gone

What with the fading light


Addressing the lost one, in fact all the lost ones:


You don’t know how I feel

I never told you

O I was much too shy

So I’ll never hold you

I hide my heart away

I have my reasons

I have my memories

Of when love was in season


So all I can do is repeat over and over, “Yeah, you, you, I’m gonna miss you, girl.”


And what does one do when that feeling strikes, when one is a person who’s older than he acts, but younger than he looks?


I turn to my guitar

And touch her silver strings

O the more I hurt

The prettier she sings

I live on the earth

And love is on a star

And if I can’t have love

I turn to my guitar


Then the lovelorn man goes out to sit alone at the café, skeptically eyeing the happy couples.  He’d warn them if he could, but that would do no good.  He hopes their love is real, misses the way they feel, but is resolved:


I don’t burn with desire

I don’t go near the fire

I think I’ll just be lonely for a while


Jesse obviously knows the feeling — he obviously knows so many feelings — but now he has a vision of the “Far Side Bank of Jordan,” and the persistence of love into eternity.  He covers this country gospel tune with hopeful prescience:


I believe my steps are growing wearier each day

Still I’ve got a journey on my mind

The lures of this old world have ceased

To make me what to stay

And my one regret is leaving you behind


He expects to be the first to go, but assures his beloved:


And I’ll be waiting on the far side bank of Jordan

I’ll be waiting drawing pictures in the sand

And when I see you coming I will rise up with a shout

And go running through the shallow water reaching for your hand


Hard to believe that Jesse Winchester – singer, player, poet, preacher, sojourner in exile — is now on the far side bank of Jordan, but his music remains there waiting for us, drawing pictures and reaching for our soul.  We will miss – yet hold close – his honey-drippin’ accent, expressive voice, sly wit, felicity of phrasing, abundant energy, and depth of spirit.


Nearly every interviewer seems to have commented on his sweet, quiet, and utterly gracious demeanor.  That grace was, and remains, his greatest gift to us.  Good-bye, Jesse old friend, and thanks for being you, and helping me be me.


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