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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Photo: courtesy of willis david hoover


Very soon I realized Arlo could play pinball with the sort of finesse he might use to fingerpick “Copper Kettle” on a downhome acoustic guitar. In short, he knew the nudges and yanks necessary to delicately influence a pinball playfield without tilting the machine. He would score massive points, rack up free games, and go ahead of me a dime or two in the process. Then I would recover, catch up, score a few free games of my own and surge past him in the dime count. Back and forth it went, all night long, amid an exciting whirl of lights, bells, thumper bumpers and ricocheting silver orbs. But, by sunup, we’d run out of quarters, free games, beer and energy. We pulled the plug.


“Well, Arlo,” I said, “you owe me 50 cents.”


“I don’t have it,” he confessed. “I spent all my money on the game. But I’ll pay you later.”


“No, you won’t,” I said with a chuckle. “What’s going to happen is I’ll take off and you’ll have forgotten to pay up. We won’t run into each other again for years and, when we do, you won’t remember you owe me 50 cents.”


“No, no,” he insisted. “I will pay you. I promise.”


We now fast-forward 29 years to Saturday, Oct. 7, 1995, and the Ironman World Championship in Kailua-Kona on the Big Island of Hawai‘i. I was in town hanging out at the King Kamehameha Hotel with Willie Leacox, my pal since grade school, who also happened to be the drummer with the rock group America, of “Horse With No Name” fame. Willie was in town because America was scheduled to perform at the event’s big closing concert on Sunday evening. The other act on the bill was none other than Arlo Guthrie.


By this time Arlo was as famous as his dad—what with the Academy Award-nominated film Alice’s Restaurant Massacree, Arlo’s famous Woodstock performance, and his classic hit recording “The City of New Orleans.”


Willie and I were on our way to have a drink upstairs in his room when we entered an empty lobby elevator and pushed the button.


Just as the doors were about to shut, an arm popped through the narrow opening, the doors reversed and in stepped Arlo. The doors re-closed, the elevator began its ascent and it was just the three of us.


Willie, who immediately recognized Arlo, extended his hand, introduced himself and said he was looking forward to working with the folk singer the following night. Arlo shook Willie’s hand and acknowledged he was a fan of America. Willie then introduced me.


“Arlo,” he said, “this is my friend Hoover.”


“It’s a pleasure to meet you, Hoover,” said Arlo with his well-known smile.


“You owe me 50 cents!” I told him. “I want my money.”


“How’s that?” Arlo asked with a quizzical expression.


“We played pinball all night at the Café Harris. You lost. You swore you’d pay me. But you never did.”


“Oh, I loved the Café Harris!” Arlo exclaimed. “I even extended my stay there! And I wrote a song called ‘Café Harris Rag’ that’s on the soundtrack to Alice’s Restaurant.”


“You also taught me a song you wrote that I now do called ‘Ramblin’ Road,’” I said.


Arlo appeared puzzled at the remark, and, after a pause, asked a question that caught me off guard: “Do you think you could teach me that song?”


“Uh, sure,” I said.

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Honolulu Magazine September 2018
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