OldiesButGoodies

Country

“Sneaking Into His Own Bar, Betting as a Kid, and Owning 125 Horses: The Side of Toby Keith You’ve Never Heard”

Country Music Memories: Toby Keith Hits No. 1 With 'Whiskey Girl'

Introduction:

Over the course of two remarkable decades, he’s released an album every fall — a rhythm as steady and grounded as the heart of country music itself. Yet when you sit down and listen to this artist speak, it’s not just the music that captivates you. It’s the stories. The texture of a life richly lived, surrounded by legends like Willie Nelson, ventures into the hospitality world, and a deep-rooted passion for horse racing that ties it all together.

He speaks with reverence about Willie Nelson, the icon whose music and spirit have long been part of American cultural heritage. “Willie is jazz,” he says, with a certain glow. “His guitar is like an extension of his soul.” For him, this isn’t just admiration from a distance. Thanks to his longtime guitarist Joey Floyd — who as a child appeared in Willie’s film Honeysuckle Rose — their worlds merged naturally. What began as musical kinship quickly became familial. “From the moment I met them, I was already part of their family.”

The respect is mutual. Willie, with his signature humor and generosity, often calls just to share a new joke — not out of obligation, but because that’s how he begins his day: spreading laughter, connecting. That warmth seems to echo throughout everything this artist touches.

Take his chain of honky-tonk bars, for instance — “I Love This Bar & Grill” — now boasting nearly 20 locations and counting. While many celebrities attach their name to a brand, he keeps it personal. He’ll occasionally drop in unannounced, sit by the bar after a round of golf, and enjoy a quiet moment before being recognized. “It took them ten minutes to figure it out,” he chuckles. “But once they did, it was whiskey time and smiles all around.”

Beyond music and hospitality, his passion for racehorses reveals another layer of who he is — someone with deep roots and a profound appreciation for tradition. Raised near the Oaklawn racetrack, he used to sneak in as a twelve-year-old, placing $2 bets through helpful adults, learning the thrill of the sport early. That passion never left. In the mid-90s, he bought his first horse for his father. The horse won its first race. “I was hooked,” he recalls. Since then, he’s built a full-scale operation: 125 mares, several stallions, and breeding operations in both Kentucky and Florida.

Remarkably, he remembers each horse by name. This isn’t just business; it’s devotion. It’s about legacy, memory, and shared joy — just like his music.

In every endeavor — whether on stage, at the track, or behind the bar — he brings authenticity, humor, and heart. It’s no wonder fans connect with him not only through the songs he sings but the stories he lives.

Video:

https://youtu.be/Xo1Co2snm4A?si=IZTy2u4zVnMBdrX6

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Merle Haggard’s childhood was becoming increasingly chaotic when something entered his life that would eventually change everything: a guitar. His older brother Lowell gave him one when Merle was around 12. Merle began teaching himself, absorbing the records and styles of country heroes such as Bob Wills, Lefty Frizzell and Hank Williams. There were no expensive lessons preparing him for Nashville. There was simply a troubled California kid listening closely and learning how another man’s sadness could live inside a melody. Merle would still make plenty of mistakes. Music didn’t instantly rescue him from running away, juvenile detention or eventually prison. But the guitar remained. Years later, millions would recognize Merle’s voice within seconds. Perhaps that’s because he wasn’t merely learning how to sing songs as a boy. He was slowly learning how to tell the truth about his own life.

Merle Haggard rarely needed to invent heartbreak. He had known it since childhood. In 1946, when Merle was only nine years old, his father, James Haggard, died following a stroke. For a boy who deeply needed his father’s presence, the loss became a turning point. His mother, Flossie, worked to support the family. Merle, meanwhile, became increasingly restless. He skipped school, ran away, got into trouble, and began a long journey through juvenile institutions that eventually led somewhere far darker. Looking back at his life, it is difficult not to see that nine-year-old boy behind many of the adult Merle Haggard’s songs. People later called him a rebel, an outlaw and a survivor. But before any of those labels existed, there was simply a grieving boy who had lost his dad—and never seemed to completely outrun that loss.

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