Toby Keith Wasn’t Just a Country Star — He Was a Serious Racehorse Owner
Most fans remember Toby Keith as the larger-than-life country singer behind songs like “Should’ve Been a Cowboy,” “How Do You Like Me Now?!” and “Courtesy of the Red, White and Blue.” But away from the spotlight, the Oklahoma legend had another lifelong passion that many casual fans may not know about: racehorses.
For Toby Keith, horse racing wasn’t a celebrity hobby he picked up for attention. It was a serious business, a personal passion, and a deep connection to the Western way of life that shaped so much of his music. 🏇🎶
Raised in Oklahoma, Toby grew up around the kind of country culture that values horses, land, grit, and competition. Long before he became one of the biggest names in country music, that world was already part of him. So it made sense that once he found success, he invested not only in music and business ventures, but also in thoroughbred racing.
Background
Keith owned and bred racehorses for years, building a respected presence in the racing community. He reportedly kept horses in training and followed their careers closely, not as a distant investor, but as someone genuinely invested in the sport. Those who knew him often said he loved the strategy, patience, and unpredictability of racing — qualities that mirrored his own long climb to country stardom.
What makes this side of Toby Keith especially interesting is how naturally it fit his public image. His songs often celebrated cowboys, small towns, working people, open roads, and the American heartland. Horse racing, with its mix of tradition, risk, pride, and adrenaline, felt like another extension of that same spirit. 🐎✨
In many ways, owning racehorses revealed something deeper about Toby’s personality. He was competitive, loyal, and willing to take chances. Those traits helped him survive the rough early years of the music business, when record labels doubted him and success was far from guaranteed. They also helped him build an empire beyond the stage — from restaurants and business ventures to philanthropy and horse racing.
Introduction
For longtime fans, this little-known chapter adds another layer to his legacy. Toby Keith was not simply a singer playing a cowboy role. He truly lived close to the culture he sang about. He understood the pride of Oklahoma, the thrill of competition, and the emotional bond people can have with animals, land, and tradition.
Even after his passing, stories like this remind fans why Toby Keith felt so authentic. His music resonated because it came from a real place. The man who sang about cowboys, grit, freedom, and American pride also spent part of his life chasing victory at the racetrack.
And that makes his story even richer.
Video
Lyrics
🎵 Let’s sing along with the lyrics! 🎤
I bet you’ve never heard ol’ Marshal Dillon sayMiss Kitty, have you ever thought of runnin’ away?Settlin’ down, would you marry meIf I asked you twice and begged you, pretty please?She’d have said, “Yes”, in a New York minuteThey never tied the knot, his heart wasn’t in itHe just stole a kiss as he rode awayHe never hung his hat up at Kitty’s placeI should’ve been a cowboyI should’ve learned to rope and rideWearin’ my six-shooter, ridin’ my pony on a cattle driveStealin’ the young girls’ heartsJust like Gene and RoySingin’ those campfire songsWoah, I should’ve been a cowboyI might of had a sidekick with a funny nameRunnin’ wild through the hills chasin’ Jesse JamesEnding up on the brink of dangerRidin’ shotgun for the Texas RangersGo west young man, haven’t you been told?California’s full of whiskey, women and goldSleepin’ out all night beneath the desert starsWith a dream in my eye and a prayer in my heartI should’ve been a cowboyI should’ve learned to rope and rideWearin’ my six-shooter, ridin’ my pony on a cattle driveStealin’ the young girls’ heartsJust like Gene and RoySingin’ those campfire songsWoah, I should’ve been a cowboyI should’ve been a cowboyI should’ve learned to rope and rideI’d be wearin’ my six-shooter, ridin’ my pony on a cattle driveStealin’ the young girls’ heartsJust like Gene and RoySingin’ those campfire songsWoah, I should’ve been a cowboy