The Ballad of the Red Headed Stranger

Staying alive, I guess, is not always something one should be lauded for. Often, it just happens, even when someone has in the past played fast and loose with their life and has actively tried to end it – with a sudden violent act or with a destructive lifestyle. Others, sure, should be commended for looking after themselves, seeing the doc regularly, eating healthy, etc. But regardless, I often shake my head in wonder that certain people are so resilient, certain notable people. This was brought home to me in September of 2022 when England’s longest-reigning monarch, Elizabeth II, passed away. 70 years she reigned and died at 96. Maybe with her it “just happened” but pretty cool nonetheless.

Seems to me that every music genre has its living legends. These men and women combine enormous popularity and influence with startling longevity enjoying careers that span decades and eras. I would argue that pop vocal has Tony Bennett, the blues has Buddy Guy and rock has Paul McCartney and others. They all, of course, hit a point when their new music is no longer consumed by the masses and enjoys no chart success but things like this matter not when you’ve reached “living legend” status. Country music certainly has Willie Nelson, an artist who really has no peer, in his own genre and even across the musical spectrum.

Willie was born in Abbott, Texas on April 29, 1933. His family – including ancestor John Nelson who was a major in the American Revolutionary War – were salt of the earth. Willie and his beloved big sister, Bobbie (1931-2022), were raised by grandparents, a couple who started their grandchildren in music. Nelson’s family picked cotton but Willie – who wrote his first song at age 7 – preferred pickin’ on his gi-tar and began playing in honky tonks at age 13.


No slacker, Willie was an active young man. He had played football, basketball and baseball for Abbott High School, raised pigs with the Future Farmers of America and played in his brother-in-law’s band in dance halls and on KHBR radio. Then in 1950, he joined the US Air Force, was married and studied agriculture at Baylor University. In 1955, while working as a DJ at a radio station, he used the facilities to make a two-song demo. When it did not incite interest, he decided to move to San Diego. From there he wandered the Pacific northwest, once sleeping in a ditch while looking for his mother. A truck driver eventually loaned him $10 and Willie took a train to Portland.

Willie moved back to Houston in 1958 and continued to shop his music to the local labels and eventually found some success. He continued to cut singles – including “Man With the Blues” (1959) – and sold songs to other artists. He made $50 for “Family Bible” and $150 for “Night Life”, a song that became a standard years later. Moving to Nashville, Nelson gained a rep jamming around the local night spots. Faron Young heard Willie doing “Hello Walls” and he decided to record it, scoring a Number One Country hit in 1961. Willie attained a real breakthrough courtesy of Ray Price. Country crooner Price cut Willie’s “Night Life” and then hired Willie to fill the bass guitar chair that had been vacated by Johnny Paycheck. While with Ray’s band, things started to pop for Willie and his songs. All at once, “Funny How Time Slips Away” was a hit for Billy Walker, Roy Orbison scored with “Pretty Paper” and then the clincher; Patsy Cline put herself and Willie into the stratosphere with “Crazy”.

Try to understand that, at this point, Willie Nelson was not really a recording artist. He had cut some singles, yes, but he was not known as a singer. By this early stage, however, he had already made quite a name for himself as a songwriter. “Hello Walls” topped the country charts and is on a short list of songs that exemplify country music of this era. “Night Life” has been recorded almost 100 times and has been particularly adopted by singers who have presented it in a jazz setting. Doris Day, Julie London, Marvin Gaye, Aretha Franklin, B.B. King and David Lee Roth have recorded it. “Funny How Time Slips Away” is nothing less than a country music staple. Elvis Presley performed it regularly in concert in the Seventies and Al Green and Lyle Lovett duetted on a Grammy-winning version that is among my Top 100 favourite songs. “Pretty Paper” is a Christmas classic and is heard 100s of times every season. And “Crazy”? Forget about it.

“Crazy” by Patsy Cline has got to be one of the most revered recordings in music history. The song is universally loved inside and outside the country music pantheon. Famously, in 1996, it became the most-played song on jukeboxes in the United States. Willie Nelson wrote the song while commuting to work and out of frustration with his unstable life with three jobs and a family to support. We pause at this point in Willie Nelson’s career – around 1961 – to consider his accomplishments. He was barely making ends meet but in a week’s time – in the course of a week – he had written the legendary songs “Crazy”, “Night Life” and “Funny How Time Slips Away”. If that had been it for Willie, he would still be a legend. But as it was he still had 60 years to go.

Willie then signed as a recording artist with Liberty Records and released his first LP, …And Then I Wrote (1961) but soon he was lured to RCA by Chet Atkins and there Willie debuted with Country Willie – His Own Songs released in 1965. Judging by the titles, these two albums were meant to capitalize on Nelson’s rep as a songwriter and to introduce him to audiences as a performer in his own right. During the late 1960s, Willie had a smattering of small hits but by 1970, the revenue generated from his publishing had dwindled after it had been invested in unsuccessful tours promoting Willie as a singer. He divorced his second wife and watched his Tennessee ranch burn down. Feeling it was time for a change, Nelson left RCA and moved back to Texas, retiring from the music business. It was 1971. Willie Nelson was not yet 40.

Coincidentally, Willie Nelson’s “retirement” started and ended about the same time that Frank Sinatra‘s did. After gigging around Austin, Willie felt rejuvenated and signed with Atlantic as their first country artist. Willie made statements with his first albums there, Shotgun Willie and Phases and Stages, an ambitious concept album. Willie Nelson the recording artist really arrived when he moved to Columbia Records in a deal that gave him complete creative control. The result was another concept album, the landmark Red Headed Stranger (1975), an album that spawned the hit “Blue Eyes Crying in the Rain”.

Willie’s breakthrough on Columbia

I have written before in these pages of the smooth pop sound of the country music from Nashville known as countrypolitan. As a response to this clean music, many artists emerged at this time to ply a sound that returned country music somewhat to its sawdust roots. Willie soon became aligned with the burgeoning outlaw country music movement and joined a gang that included men he would collaborate with over the next decade; Waylon Jennings, Kris Kristofferson, Merle Haggard and others.

In the late Seventies, Willie continued to blaze his own trail. He scored with a duet album with Waylon that included the smash “Mamas Don’t Let Your Babies Grow Up to Be Cowboys” but then Willie made a sharp turn and issued an album the industry claimed would ruin his career. Knowing better, Willie Nelson may have originated a trend that continues to this day.

Stardust was Willie’s album offering in the spring of 1978. The record was produced by Willie’s neighbour in Malibu, the legendary Booker T. Jones. Stardust was an album of standards that had Columbia baffled as this was as far away from outlaw country as you could get. But here we see another example of Willie’s vision and his willingness to follow his muse. We also see confirmation that his influences extended far beyond the confines of country and hillbilly music. The LP featured Hoagy’s title track, “Blue Skies”, “Moonlight in Vermont” and others from the Great American Songbook. How many times have I run across stories of the record company being dead wrong when it came to an artist’s vision? The album was a Number 1 Country album – in fact, it stayed on Billboard‘s Country album charts for ten years – and entered the Top 30 on the Pop album charts. The success of this album that was recorded in Willie Nelson’s living room in ten days landed Nelson on the cover of Newsweek under the heading “King of Country Music”. Obviously, Willie helped blur the lines between country and jazz/pop music.

Dig this shot of Willie with friend, neighbour and collaborator Booker T. Taken at Willie’s Cut ‘n’ Putt, a 9-hole golf course and recording studio, in Spicewood, Texas.

As the Seventies gave way to the Eighties, Willie was perhaps the most visible country artist in the world. Hit singles included “My Heroes Have Always Been Cowboys”, “On the Road Again” and the stunning “Angel Flying Too Close to the Ground”. Also at this time he turned to acting debuting in The Electric Horseman and then starring in Honeysuckle Rose with Amy Irving with whom he had a short relationship. He then added Michael Mann’s Thief in 1981 and continued acting regularly mostly in westerns but he also joined the prolific list of guest stars on Miami Vice.

In ’82, Nelson joined Merle Haggard to release the album Pancho & Lefty. Produced by Chips Moman, the sessions for the album featured guitarist Johnny Christopher who had co-written “Always On My Mind”, a song that was included on the record and became another hit for Willie. The tune reached Number One Country, number 3 Pop and won three Grammys. By the end of the decade, Nelson had joined Waylon, Kristofferson and Johnny Cash in the supergroup The Highwaymen and was involved in the recording of “We Are the World” for USA for Africa. The 1990s and beyond found Willie Nelson enjoying his victory lap, performing and recording regularly on his own and with a host of guests and companions. But it might be time now to discuss two other well-known elements of the Nelson legend.

Today, Willie is known for his use of marijuana almost as much as for his music; certainly the younger generation have taken him to their bosom due to his advocacy of the legalization, regulation and taxation of cannabis. This of course has been the source of much comedy as many have joked about Nelson’s support of happy smoke. But to Willie it has always been a serious subject. Once a heavy whiskey drinker and a mean drunk, Willie turned to mary jane in the late 60s and has always claimed that it “saved his life”. He maintains it is medicinal and has often railed against the government’s handling of it and at society’s perception of users. In 2019 at age 86, Willie finally quit smoking boo saying he had abused his lungs long enough. “I think that weed kept me from wanting to kill people. And probably kept a lot of people from wanting to kill me, too — out there drunk, running around.”1

While Willie’s love of Mary Warner may have sparked up the idea to record a reggae album in 2005 called Countryman, truth be told, Nelson’s tangles with the IRS may actually have had more of an impact on his recorded output than his recreational habit has. When Nelson returned to the music business after his short sabbatical, he hired as his manager one Neil Reshen who successfully negotiated Willie away from RCA and oversaw Willie’s signing to Atlantic. Unfortunately for Nelson, some years later he learned that Reshen had not been paying Willie’s taxes to the IRS, a practice that was, Willie claimed, continued in bad faith later by his accountants at Price Waterhouse. In 1990, Uncle Sam decided he had had enough and seized Willie Nelson’s assets claiming the singer owed $32 million. Willie’s financial difficulties intensified until his lawyer was able to renegotiate Nelson’s debt down to $6 million. To pay this debt, Willie auctioned many of his possessions – many purchasers gifted the items back to their hero – but perhaps more significantly he began recording albums en masse in the hopes that the revenue generated would satisfy his creditor.

There was not much left to the imagination then when Willie released The IRS Tapes: Who’ll Buy My Memories? in June of 1991. The well-received album featured only Willie and his guitar, Trigger, and generated $3.6 million dollars for the IRS. The albums then came fast and furious and when this is considered along with Nelson’s endless touring it makes one think that poor Willie – a legend by this point, mind you – was starting all over again and hoped to restock his emptied bank accounts. One clue to this for me at least is that Willie would record and release an album for any and all labels that were interested. Consider that each of his next ten albums were recorded for a different label. Starting with The IRS Tapes in ’91 and ending at Rainbow Connection 10 years later, Willie Nelson released 16 albums; four for Island and the rest were all for different labels.

Perhaps another line can be drawn starting in the wake of The IRS Tapes. Willie may simply have taken a different view of recording. Judging by the albums he’s released since then – in those 31 years he’s released 33 records – it seems Willie is making the most of the time he has left. He has recorded albums of many different stripes, often gathering his friends and family to make music with him. There have been records with Waylon Jennings, Don Cherry, sister Bobbie Nelson and sons Lukas and Micah, Ray Price, his old patron, Merle Haggard and Asleep at the Wheel. He has revisited the standards no less than seven times including Somewhere Over the Rainbow, a Number One Country record from 1981, Night and Day, a rare instrumental album and Summertime: Willie Nelson Sings Gershwin (2016).

Willie’s done a gospel album and a Christmas album with his sister, records devoted to songwriters like Cindy Walker and artists like Ray Price and he’s released albums that have documented the history of country music. Also notable in Willie’s latter-day catalogue are his two records focusing on songs associated with Frank Sinatra.

May 23, 1993

Like Bob Dylan, Nelson has looked to Sinatra in his old age and found much resonance in the work of the Chairman. He issued My Way in 2018 and like Dylan again, Willie certainly brings a different vocal sound to these classic songs, applying his barn board pipes to tunes like “Summer Wind”, “It Was a Very Good Year” and the title track. Nice to know that Willie and Frank knew each other and admired one another’s work. They performed on the same bill at the Golden Nugget in Vegas in the 80s and appeared together in a PSA for the Space Foundation. My Way would win Willie Nelson the Tony Bennett Grammy for Best Traditional Pop Vocal Album.

Three years later, Willie issued That’s Life sporting a stellar album cover. Recorded at Capitol Studios, this time Nelson essayed “A Cottage for Sale”, “In the Wee Small Hours of the Morning” and “I Won’t Dance” with Canadian Diana Krall. Willie is an appropriate interpreter of these songs and the fact that he does FS this late in the game is poignant. The Sinatra-inspired records add much to his legend and they are proper capstones to a vast body of work that allows Willie to align himself with the great purveyors of song like Frank and Bob Dylan. An argument could be made that this triumvirate represents the very pinnacle of storytelling in song. Like these other two greats, Willie has lived life and has shared his findings. Not so much for his own gain but to benefit us all with the wisdom he’s gleaned from earthly experience. It has been a selfless endeavour.

Willie has won 10 Grammy Awards. He has scored 17 Number One records on the US country charts; this includes soundtrack records, a greatest hits album, a compilation made with others and a live album. In the 57 years between 1965 and 2022 – and that is staggering longevity for a recording artist – Willie charted a total of 86 record albums on the Country charts. Of these 86, 51 of them – or two-thirds, half his studio LPs – reached the Top Ten. So, it’s not just quantity, it’s quality. In a run between Red Headed Stranger in ’75 and Stardust in ’78, 5 of his 6 records topped the Country charts. Between 1975 and 1985, 19 Willie Nelson records reached the top 5. Finally for us Stats Freaks; 27 of his own singles reached the Top Ten and add to that 18 Top Tens recorded with others. Willie topped the Country singles charts 12 times and added another 11 Number One songs with collaborators. Thems the facts. But it’s about so much more than numbers.

Into the fall of 2022, Willie Nelson was 89 years old and was still touring and playing small clubs and music festivals. He is not just a survivor, a holdover from the classic era who is still out there. He is Willie Nelson, probably the most popular and significant country artist of the last fifty years and among the most influential C&W singers of all-time. In many ways – not the least of which is his Willie’s Roadhouse channel on Sirius XM radio – he continues to champion the legends of his genre, the voices of his youth and of his life. In fact, Willie Nelson transcends his genre while at the same time he defines it.

Ten from Nelson

  • Blue Eyes Crying in the Rain
  • Can I Sleep in Your Arms
  • Angel Flying Too Close to the Ground
  • Always On My Mind
  • The Last Thing I Needed
  • City of New Orleans
  • Seven Spanish Angels (with Ray Charles)
  • Highwayman (with The Highwaymen)
  • The Maker
  • For the Good Times


  1. Alexander, Bryan. Willie Nelson has quit smoking marijuana for health reasons: ‘I have abused my lungs’. USA Today. (2019)


    • It is fascinating that someone can have so much music in them. Presented in different way and formats with different people…but just music, music, music. Whether you love him or are indifferent, you gotta hand it to Willie Nelson.

  1. By sheer coincidence, I was just listening to a BBC podcast featuring legendary British music journalist and broadcaster, Whispering Bob Harris, who was talking, amongst other things, about his friendship with Lukas Nelson. When Bob was recently gravely ill, Lukas made time during a very tight schedule in the UK, caught the train to Bob’s house and quite literally gave him the shirt off his back in appreciation for the support Bob had given him through his broadcasting. His lyric, ‘stop watching the news and build a garden’, is a real lesson for our time, I think. Talent and kindness clearly runs in the Nelson family.

    • Seems it’s true. Willie has clearly fostered a goodwill approach to life and this has permeated his family and friends. The book I’m reading contains passages written by his wife, children and band members and it is confirmed that Willie is one of the good ones. “Sidemen” who are so much more and have been with him for 30-40-50 years. Willie Nelson is truly a unique personage.

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