Cash was not a rock and Roll star.He had a prime-time network country music variety show in 1969.
The fact that you mention that Cash was "heavily into drugs and booze" is pretzel logic. He would not have "fit right in". He was more like the shooter in Easy Rider, than the bikers.
You couldn't be more wrong here. Cash was played on country radio, but for the most part he shied away from the Nashville establishment throughout his career, beginning in the '50s when be was based out of Memphis, to the early '60s when he mostly stayed in California, to the '70s and '80s when he associated himself with the outlaws of country music like Waylon Jennings, Willie Nelson and Kris Kristofferson, and even into his final years when he was embraced by the alternative rock crowd far more than the country establishment. By the time of Woodstock he'd played the Newport Folk Festival several times appearing alongside Dylan, Baez, Ochs, and others. He'd recorded an album of songs empathizing with Native Amerit and it's lead single was banned by many country stations and he was branded a "race traitor." He'd recorded with Dylan the previous year.
His variety show was not a "country variety show" either. While he did have plenty of country acts on the show, the music presented truly was a variety. Dylan and Joni Mitchell were the first guests and over the years he had on Creedence Clearwater Revival, Derek and the Dominoes, Arlo Guthrie, Neil Young, etc. A casual glance at a few of the guests shows a true melting pot of music: Louis Armstrong, Neil Diamond, Mahalia Jackson, George Jones, Roy Orbison, Bill Monroe, Odetta, Stevie Wonder, Tony Joe White, Merle Haggard, and Pete Seeger in his first television appearance since the controversy he caused on the Smothers Brothers show.
Also very interesting is the fact that you equate Cash with the shooter in Easy Rider given that he actually had Dennis Hopper on his show to read poetry.
He would have played Woodstock if asked and if this video of Cash playing a college around the same time is any indication, he would have won the crowd over:
https://youtube.com/watch?v=t51MHUENlAQSome more videos that may be of interest:
https://youtube.com/watch?v=FQq0dw7rmtc A (very stoned) Johnny Cash discusses and sings about the plight of Native Americans alongside Pete Seeger in 1964 or '65
https://youtube.com/watch?v=5HFUSft_I9s Cash speaks a bit about the "hippie movement" and performs a song he'd written about them. He performed the same song for Richard Nixon at the White House.
https://youtube.com/watch?v=EQAXTvcMoMA Cash's thoughts on Vietnam in song.
https://youtube.com/watch?v=AM4lxPcUozw Studio recording from the height of the Civil Rights movement
And finally Cash on MLK and RFK
https://youtube.com/watch?v=KjCm9ZnDTMc
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