Waylon Jennings participated in a celebrity roast to raise funds for the Spina Bifida Association in November 1985, but Johnny Cash made sure his long-time friend, collaborator, and fellow outlaw country icon got a bit pre-roasted. Jennings, his wife, Jessi Colter, Kris Kristofferson, and Willie Nelson were all a part of the fundraising event. Johnny Cash and June Carter Cash were also slated to attend, but they weren’t able to make it from their home in Jamaica.
Some newspapers reported that the country music power couple was at the Spina Bifida Association benefit. However, a letter Cash wrote to Jennings in lieu of attending the roast would suggest otherwise. The tongue-in-cheek note didn’t explain the exact reason why he couldn’t attend. But a likely enough reason would be that the Cash family was enjoying their time at “Cinnamon Hill,” their Jamaican estate. Cash’s health was also somewhat unstable at this time, due to ongoing addiction and developing long-term ailments.
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Roast attendance aside, the letter is a hilarious example of the type of humor that develops between two men like Waylon Jennings and Johnny Cash. The same two men who lived as strung-out bachelors together for a time outside of Nashville. Figureheads of a rough-and-tumble subgenre of country, outlaw country. And after all, you know a roast will be good when the roaster lands a punchline within the first sentence.
Johnny Cash Wrote Waylon Jennings a Cheeky Apology Letter
From his home in sunny Jamaica, Johnny Cash sent a letter over to the States for Waylon Jennings. The letter began, “Waylon, this roast shouldn’t hurt you too much tonight because your brain is already fried. Seriously, I wanted to be there so bad. But I have been told that the only way to get from Jamaica to Atlanta is to travel. I sincerely hope you will accept this honest reason. We miss you and Shooter. Did you ever find out who Shooter’s mother is…”
“I love you, Jessi,” he continued. “Don’t I, June? Jessi, you are one of the few truly great women I have met in my entire life. As soon as we get home, we want you to find Waylon’s clothes that he is going to wear that day, then show him where the car keys are, and come to see us. Waylon, I love you. Don’t I, God? Just remember if you’re ever down to your last dollar, if all your old friends turn their backs on you, if you’re so low that you wish you could die, just remember, I’ll always be…” Then, he signed the letter, “Johnny Cash.”
Guernsey’s Auctioneers included this letter from Cash to Jennings in a 2014 liquidation sale of the latter country artist’s estate. The auction took place in early October of that year at the Musical Instrument Museum in Phoenix, Arizona. Cash’s “pre-roast” letter to Jennings sold for $2,750. Interestingly, a letter from John Lennon to Jennings went for $7,500. But we have to assume that price discrepancy is because correspondence between the British rock ‘n’ roller and Jennings would’ve been less likely than between him and Cash.
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