Introduction
The Day Waylon Jennings Changed a Boy’s Life in Waverly
On a freezing morning in Waverly, Tennessee, outlaw country music legend Waylon Jennings stepped off his tour bus into a low, gray station parking lot. Coming off a late-night show in Nashville with a voice raspier than usual, Waylon was simply looking for a quiet, black coffee and 20 minutes to himself. However, a thin, off-key whistling caught his attention.
Sitting on an overturned milk crate was an eleven-year-old boy named Tommy Wade Hollis. Beside him was a wooden shoe shine box. Tommy was working on a man’s boot with intense focus while humming “Good Ol’ Boys”—the theme song Waylon sang every Friday night on national television. Touched by the sight, Waylon walked over, sat down, and struck up a conversation.
As Tommy shined Waylon’s boots, the story of his family unfolded. Tommy had been shining shoes since November to help support his mother, Ruth, and seven-year-old sister, Dot. Ruth had recently lost her long-time job when the local shirt plant shut down. The rent was $18 a week, and wash money wasn’t enough to stretch. Tommy spent his daily earnings of two or three dollars just to help keep the lights on.
Seeing his younger self in the hardworking boy, Waylon resonated deeply with Tommy’s spirit. When Ruth came outside to fetch her son, Waylon greeted her with profound respect. He pulled out his iconic black-leather guitar and played a soft, intimate rendition of “Good Ol’ Boys” right there on the sidewalk. Afterward, he invited the whole family to the station diner for a warm meal.
Waylon didn’t just offer sympathy; he took quiet action. Before leaving town, he had his tour manager discreetly arrange a steady job for Ruth as a cook at a nearby diner. He worked with the local store owner, Earl, to build Tommy a proper, permanent shine stand. Anonymously, Waylon also covered a month’s rent for the family. Over the following year, plain envelopes postmarked from various tour stops arrived at the store containing cards that simply read: “Stay stubborn.”
Supported by Waylon’s quiet generosity, the family got back on their feet. Tommy saved his earnings to buy his sister her first guitar, passing forward the grace he had received. Years later, long after Tommy passed the shine stand down, he kept one special brush. Carved into its handle were those same two words of encouragement that carried him through: Stay stubborn.