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The Story of How Singer-Songwriter Arlo Guthrie Owed Me 50 Cents Over a Bet

A ramblin’ road or an adventure that started with a bet with singer Arlo Guthrie over a pinball game in Missouri, then ricocheted through the decades to Kailua-Kona and Honolulu.


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Click on the image for a larger view. 
here, arlo guthrie’s handwritten lyrics to “ramblin’ road,” along with the pick he gave hoover.

By then the elevator had arrived at Arlo’s destination floor, and the doors slid open. Outside two smiling women were waiting to greet him. Arlo stepped out, put his right arm around the shoulder of one of the women, who was holding a child, and as the elevator doors were closing, he motioned toward me with his left hand and said, “That guy right there is going to teach me a song I wrote.”


And right here is where I customarily end the tale with, “And so the doors go shut—and I STILL haven’t got my 50 cents!” … But, then, I add sheepishly, “I still haven’t taught him to play ‘Ramblin’ Road,’ either.”


The line usually gets a laugh. And then I do the song.


But there’s more to our little tale. It started the evening after the elevator incident, during the big outdoor concert finale. Arlo took the stage as an immense crowd looked on. Along with Willie and his fellow America band members, who were waiting to perform next, I stood several yards from the edge of the stage in a roped-off area.


As we watched, I marveled at Arlo’s ability to capture and hold the crowd—to play the audience with ease and expertise, as he might his guitar, or a pinball machine.


And when his songs and stories had ended, and he had done his encore, taken his bows and acknowledged the cheers of a grass to where I was standing and, without a word, handed me his well-worn guitar pick. And then he drifted away.


 I must admit I was moved by his gesture.


As fate would have it, two days after Arlo handed me his guitar pick, a book I’d written was published by Guitar Player magazine. Titled, Picks! – The Colorful Saga of Vintage Celluloid Guitar Plectrums, it was the first history of guitar picks ever written. It featured hundreds of color photographs of kaleidoscopic, translucent celluloid picks, miniature works of art and engineering marvels with wire loops, corks and corrugated holes. It told the story of remarkable characters and inventive devices that evolved into the one-inch, rounded-isosceles triangle recognized today as the “standard guitar pick”—a pick exactly the shape and dimensions as the one Arlo had handed me. Except that Arlo’s not only included his imprint, but his DNA.


To my amazement, Picks! did better than I could have imagined. Thousands of copies sold worldwide, and it was lauded by critics as a definitive study. Chet Atkins and B.B. King wrote blurbs for the book. Suddenly, I was “the picks guy,” doing magazine, radio and television interviews about a tiny subject folks suddenly found fascinating. David Bonsey, the musical instrument expert seen on the PBS Antiques Roadshow, valued the collection of 400 picks featured in Picks! at $10,000.


Thanks largely to encouragement from Bonsey, I received a letter from the director of the National Music Museum, a world-class musical research institution, saying the museum would be honored to have my pick collection and research materials. I donated the entire hoard—40 pounds of research, all 400 Picks! picks, plus the remainder of the 8,852 vintage plectra I had collected from scores of sources scattered across the land of the free.


One pick, however, I did not give away. One pick I kept for myself. 


One pick is now a collection unto itself. And that’s Pick No. 8,853—the pick Arlo handed me that night on the Big Island of Hawai‘i.


In January 2011, I did a concert at the Atherton Performing Arts Studio in Honolulu that included my rendition of “Ramblin’ Road,” as well as my all-night Café Harris pinball yarn. A video of that segment eventually reached the Internet and made the rounds.


Thus, on April 18, 2014, I received an Express Mail package containing two 25-cent pieces taped to an envelope containing an “Arlo D. Guthrie” check in the amount of $3.73, which, according to the memo line, was “adjusted for 50 years of inflation – paid in full.”


All at once, I was the obligated party!—obliged to fulfill my “Uh, sure,” elevator pledge to teach Arlo his own song. In desperation, I scrambled and found a YouTube, mid-1960s film clip of Arlo actually singing 48 seconds of “Ramblin’ Road.” I wrote his daughter Cathy (whose “Authorized Signature” appears on the check for $3.73 check), asking her to let Arlo know.


I launched an exhaustive search to locate a “Ramblin’ Road” lyric sheet—written in Arlo’s own hand at Café Harris in 1966. It took a couple of years, but my brother Russ finally stumbled across the thing stashed in a dusty closet at his home in Missouri.


And if I ever bump into Arlo again, I’ll sure show him everything I know about the chords to “Ramblin’ Road.” While I’m at it, I’ll challenge him to a pinball match, provided we can find some joint that still has a machine.


Otherwise, I’ll buy the first round. Seems like the least I could do.



About the Author

Photo: David Croxford

Author Willis David Hoover has worked as a folk singer, a musician, a roving newspaper reporter, a barkeep, a Nashville songwriter and a recording artist. He is currently writing a memoir about fate, and the heroes, villains, misfits and exceptional characters he has encountered along his journey. This is the first time this entire tale has been told in print.




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