During the late 1950s, Crosby was a member of a local Oneonta teen band called The Tones. The band traveled to Philadelphia to audition for Dick Clark's "American Bandstand", but were turned down. Members of the band found Dick Clark's house and were able to get a recommendation to audition at New York City's Baton Records through the company's lead producer Sol Rabinowitz. The band was given a recording contract, but the studio wanted a quintet backed by studio musicians, which left Crosby and another member out of their recordings.
After high school, Crosby joined the National Guard, but his thirst for adventure led him to go AWOL and roam the country busking for a living in areas like New Orleans, Texas, Florida, and New York. He played mostly ukulele until Harriet Ottenheimer, one of the founders of The Quorum, got him settled on a guitar in 1963. He adopted his stage name "Jerry Jeff Walker" in 1966. He spent his early folk music days in Greenwich Village in the mid 1960s. He co-founded a band with Bob Bruno in the late 1960s called Circus Maximus that put out two albums one with the popular west coast hit "Wind", but Bruno's interest in jazz apparently diverged from Walker's interest in folk music. Walker thus resumed his solo career and recorded the seminal album "Mr. Bojangles" with the help of David Bromberg and other influential Atlantic recording artists. He settled in Austin, Texas, in the 1970s associating mainly with the country-rock outlaw scene that included artists such as Willie Nelson, Guy Clark, Waylon Jennings, and Townes Van Zandt.
"Mr. Bojangles" (written by Walker) is perhaps his most well-known and most-often covered song. It was about an obscure alcoholic but talented tap-dancing drifter, (not the famous stage and movie dancer Bill Robinson, as usually assumed). Bojangles is thought to have been a folk character who entertained informally in the south of the US and California, and some say he might have been one of the most gifted natural dancers ever. Authentic reports of him exist from the 1920s through about 1965. Artists from Nina Simone to Bob Dylan, Philip Glass to the Nitty Gritty Dirt Band, have covered the song. Walker has also recorded songs written by others such as "LA Freeway" (Guy Clark), and "Up Against the Wall Red Neck Mother" (Ray Wylie Hubbard).
A string of records for MCA and Elektra followed Jerry Jeff's move to Austin, before he gave up on the mainstream music business and formed his own independent record label. Tried & True Music was founded in 1986, with his wife Susan as President and manager. Susan also founded Goodknight Music as his management company and Tried & True Artists for his bookings. A series of increasingly autobiographical records followed under the Tried & True imprint. Tried & True also sells his autobiography called "Gypsy Songman". In 2004, Jerry Jeff released his first DVD of songs from his past as performed in an intimate setting in Austin, TX.
He interpreted the songs of others like Rodney Crowell, Guy Clark, Keith Sykes, Paul Siebel, Bob Dylan, Todd Snider and even a rodeo clown named Billy Jim Baker.
His son, Django Walker, is also a musician. In addition to his residence in Austin, Walker had a retreat on Ambergris Caye in Belize where he recorded his "Cowboy Boots and Bathing Suits" album in 1998.
Members of his band varied over the years. The Lost Gonzo Band and the Gonzo Compadres have backed him in the past. Key members of his band included Craig Hillis - guitarist and arranger on Viva Terlingua, John Inmon, Freddy Krc, Gary P. Nunn, Bob Livingston, Bobby Rambo, Mitch Watkins, Steve Samuel, David Bromberg and others.
Tryin' To Hold The Wind Up With A Sail
Jerry Jeff Walker Lyrics
Jump to: Overall Meaning ↴ Line by Line Meaning ↴
Well somewhere the sun today's soakin' up a cornfield dry
But it's shining a love song on some snowy clouds
And I know my fingerprints will be brushed away
By the hard plate every day of the century
But the other night when you cried and you woke me upJust to tell me of your bad dream
I held you close to be of some avail
Tryin' to hold the wind up with a sail
We turned again and stood upon that gentle land
It's a vulnerable drum of old moss and sand
We could rise up another hot naked wall if we stand tall
We can face it again, it's the same old wind
But last night when you cried and woke me up
Just to tell me it's all a bad dream
I tried to hold you to be of some avail
Like tryin' to hold the wind up with a sail
Whenever you cry and wake me up and tell me you know
That it's all a bad dream
I want to be there to hold you to be of some avail
Tryin' to hold the wond up with a sail
The lyrics to Jerry Jeff Walker's song "Tryin' to Hold the Wind Up With a Sail" poetically describe the fleeting nature of life and love, as well as the futile attempt to try and hold onto them. The opening lines set the scene, describing the sun shining on a cornfield that will soon be gone, followed by a bittersweet acknowledgement that our existence on earth is fleeting and temporary. The verse then shifts to a more personal level, with the singer comforting their partner during a bad dream by holding them close, despite the knowledge that their touch can't truly protect them from the harshness of life.
The second verse takes a more hopeful stance, describing the ability to rise up against challenges if we stand tall and face them head-on, but again acknowledging the inevitability of the wind that will ultimately knock us down. The final stanza is a repeated assurance that the singer will always be there to hold their partner and be a source of comfort, even if their efforts are as futile as trying to hold the wind up with a sail.
Overall, the song speaks to the universal human desire to hold onto things that we know will eventually slip away, whether they be moments of joy or the people we love. It acknowledges the sweet sorrow of trying to hold onto things that we know will ultimately be gone, while also offering comfort in the knowledge that we can still find meaning and purpose in our interactions with others.
Line by Line Meaning
Well somewhere the sun today's soakin' up a cornfield dry
The sun is shining so bright on a dry cornfield somewhere.
But it's shining a love song on some snowy clouds
The sun is creating a beautiful scene on some snowy clouds.
And I know my fingerprints will be brushed away
I know my mark will fade with time.
By the hard plate every day of the century
Due to the constant abrasion the earth undergoes over time.
But the other night when you cried and you woke me up
The other night when you woke me from your tears.
Just to tell me of your bad dream
Just to confide in me about your troubling dream.
I held you close to be of some avail
I hugged you tightly to comfort and help you.
Tryin' to hold the wind up with a sail
Trying to control the uncontrollable, similar to capturing wind with a sail.
We turned again and stood upon that gentle land
We both faced our problems and returned to familiar ground.
It's a vulnerable drum of old moss and sand
Despite its fragility, the land has stood the test of time.
We could rise up another hot naked wall if we stand tall
Despite future challenges, we could stand strong and face them.
We can face it again, it's the same old wind
We can confront our problems again, it's just a recurring struggle.
But last night when you cried and woke me up
But when you cried last night and woke me from sleep.
Just to tell me it's all a bad dream
You confided that it was just another troubling dream.
I tried to hold you to be of some avail
I attempted to embrace you tightly and ease your worries.
Like tryin' to hold the wind up with a sail
Attempting to control something uncontrollable, like the wind with a sail.
Whenever you cry and wake me up and tell me you know
Every time you wake me from tears and say you understand.
That it's all a bad dream
That your worries are just bad dreams.
I want to be there to hold you to be of some avail
I want to comfort and console you in any way possible.
Tryin' to hold the wind up with a sail
Attempting to control the uncontrollable, like holding wind with a sail.
Lyrics © O/B/O APRA AMCOS
Written by: PAT GARVEY
Lyrics Licensed & Provided by LyricFind
@UNKAGLEN
The pop of the turn table, back when the music was real, and so was the artist..thanks for sharing.
@TheTigers2758
Saw Jerry Jeff many times in Corpus Christi , Texas,at the Yellow rose during the late 70s, singer /song writer/musicians.. sounded just like the albums. this is one of my favorite Jerry jeff songs...Jacky jack!!! Austin ,Texas i am heading home soon.
@mrvngrdns1
Doesn't get any better than this Jacky Jack! Your "glory days". Brings me back.....
@vicwhaley7066
Met Jerry at a concert in Santa Cruz, CA I was a bouncer....incredible individual. What happened to his MC'ing Austin City Limits. A true hero of mine.
@likeriver
My dad's a big JJW fan. I don't really listen to his music much, but I had this song on my ipod and was suprised to see that my dad didn't know this song until he heard it playing on my ipod in the car.
@virnan
used to hear this when my dad was partying. Just a little youngster when this came out. Great tune always will remember this and Contrary to Ordinary.
@rickymartinez719
Ha Ha remember being in Atoka, Oklahoma and Jacky Jack came on stage and gave David Alan Coe The finger when DAC started talking smack on JJ..Never forget it back in '76. 48 hours in Atoka!
@jamiethompson7302
I was there it was crazy I live about three miles from there now
@anthonyervin765
Dig that Billy the kid album cover
@virnan
This portrait of Jerry is a rehash of the famous Billy the Kid photo where Billy is leaning on his rifle, instead of a guitar.