There are three major milestone Williversaries to celebrate this year: Willie Nelson (b. 1933) turns 90 years old today; and 2023 also marks 50 years since his annual 4th of July Picnic and the release of his landmark 1973 album Shotgun Willie, heralding the debut of the "New Willie": long-haired (later braided), unshaven, hippie-influenced, pot smoking, and Austin-based. '
Of COURSE there was an older incarnation of Willie Nelson. He was 40 years old when he reinvented himself. Prior to the metamorphosis he was a much more conventional and traditional figure in the country music business. Check it out:
Whoa, man! Grow a beard! Look like Governor George Wallace!
A musician since childhood, Nelson been struggling along in country music since the mid-50s, though he'd played school dances and such since the age of 13 (1946). He'd been a farm kid, served in the Air Force, and worked as a dishwasher, a D.J., and a door-to-door salesman. In the early '60s, he broke into the biz as a Nashville songwriter penning several tunes that became enduring American standards: Patsy Cline's #9 hit "Crazy" (1961), "Hello, Walls" (a #12 hit for Faron Young in 1961), "Pretty Paper" (a 1963 hit for Roy Orbison), "Night Life" (a 1963 hit for Ray Price) and "Funny How Time Slips Away" (a #13 for Joe Hinton in 1964, but much covered by others). Nelson became a recording artist himself in 1962, recording 15 albums prior to his reinvention. Those familiar with these tunes know that Nelson was already outside of the box: there's plenty of tasteful jazz/Tin Pan Alley influence in his songs, though the themes, instrumentation, and performances keep them closely knit to country.
By the late '60s and early '70s, several rock and pop artists like The Byrds, The Eagles, and Linda Ronstadt had popularized country rock, and there were some interesting cross-over team-ups (such as Bob Dylan and Johnny Cash). It seems a natural development that some country artists would ride towards the middle ground from their side of the border. This became known as "Outlaw Country". Cash and Nelson were major figures in this innovation, along with Waylon Jennings, Kris Kristofferson, Hank Williams Jr, and others. The younger, good-looking Kristofferson's crossover appeal proved greatest; he became a movie star. Cash, while scarcely altering his already rebellious persona, had his own network TV show, and also managed to break out of the country silo. Nelson was (and is) not far behind them, however.
Nelson's 1975 concept album Red Headed Stranger, proved the break-through. Itv was composed mostly of standards written by other artists, one of which Fred Rose's "Blue Eyes Crying in the Rain" became his first major pop hit as a singer. In 1978 came the collaboration Waylon and Willie, which yielded the hit single "Mama, Don't Let Your Babies Grow Up to Be Cowboys". That same year he raised eyebrows (and his critical status) by daring to release Stardust, an album entirely of Tin Pan Alley standards like "Georgia On My MInd", "Blue Skies", "All of Me" and the title track. When I think of him in my mind's eye, it's usually singing one of these soulful, melancholy numbers, accompanying himself with that old brown damaged acoustic guitar he calls "Trigger", after Roy Rogers' horse, I guess.

In 1979, Nelson made his film debut with a small role in The Electric Horseman with Robert Redford and Jane Fonda. By the following year he starred in his own movie, Honeysuckle Rose, named after his tour bus, supported by Dyan Cannon, Amy Irving, Slim Pickens, Emmylou Harris et al. Look at that poster! TWO chicks! That's way more rock and roll, than it is country. Country singers usually make mistakes in the bedroom, get drunk, and cry about it. Willie Nelson smokes pot and gets philosophical! "Maybe I'll see ya down the road sometime, baby". (I don't know if that's a real line, just sounds like something he'd say). The movie's theme song "On the Road Again" was a major hit, and is one of those ear-worms you just can't shake. My brother used to sing the first line of it compulsively, at first just when he was getting into his car to leave, but eventually every five seconds.
In 1982 Nelson had an even bigger hit with the ballad "You Were Always On My Mind". In the mid '80s came team-ups, including the unlikely duet with Julio Iglesias "To All the Girls I've Loved Before", and his ongoing collaboration with the supergroup The Highwaymen, whose members included Jennings, Cash and Kristofferson. Over the next decade, this Outlaw configuration recorded several albums together and made several western movies, mostly for television.
Since then he has collaborated with seemingly everybody, across every musical genre known to man. In the process he has become one of the most beloved figures in American pop culture (ranking with his fellow country crossover artist Dolly Parton, whom, naturally he has also collaborated with. His willingness to promote progressive causes has alienated some of his conservative fan base, but you know what? The loss is all theirs. Something just occurred to me: Willie Nelson is one of the few artists I would dearly love to see live (I hate attending live music concerts). It would be like visiting Mount Rushmore and seeing the Presidents faces come to life (especially if I smoked some Willie's weed!) And you know what? I may still have a chance to do this. After all, his most recent album was released just last month. And coming up: his 50th annual Fourth of July Picnic! And this guy started out in music before Elvis was a thing! How crazy was that! Don't forget to take your Recommended Daily Allowance of Cannabis, Children!
To learn more about show biz history please see my book No Applause, Just Throw Money: The Book That Made Vaudeville Famous. And stay tuned for my next book Vaudeville in Your Living Room: A Century of Radio and TV Variety, coming November 2023.
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