Sometimes the cowboy who taught America how to ride tall in the saddle and tip a hat with a smile is the one who leaves the biggest boots to fill. On this day back in 1998, the world lost Roy Rogers, the King of the Cowboys, but fans still tip their hats to a legend who made the Wild West feel just a little more golden.

Long before every Nashville upstart was calling themselves an outlaw, Roy Rogers was the real deal. Born Leonard Franklin Slye in a dusty Cincinnati neighborhood, he didn’t grow up surrounded by Hollywood lights or studio handlers. He learned to yodel on the banks of Duck Run, called square dances at local hoedowns, and dropped out of high school to help put food on the table. There was nothing fancy about it. Just a kid with a big voice and a bigger dream.

When Roy and his dad packed up the car in 1930 and headed to California, it wasn’t fame they found waiting. It was hustle. He sang on L.A. radio shows, scraped together gigs, and finally found his shot when he formed Sons of the Pioneers. That’s where “Cool Water” and “Tumbling Tumbleweeds” started rolling off the prairie and into movie houses all across America.

Hollywood had Gene Autry first, but when Republic Pictures needed a new singing cowboy, they told Leonard to ditch the name. He took Rogers to honor humorist Will Rogers, and Roy just because it sounded strong enough to ride a horse through a hailstorm. And ride he did, through more than a hundred films, countless radio hours, and TV shows that brought dusty trails and campfire songs into suburban living rooms.

People forget just how huge Roy Rogers was. This wasn’t just a guy on horseback shooting blanks at outlaws. He was BoxOffice magazine’s top star for nearly a decade. He and his Queen of the West, Dale Evans, were TV gold. They wrote and sang “Happy Trails,” a song that still plays like an old friend humming you home after a long ride.

When you look back, what hits hardest isn’t the three Hollywood Walk of Fame stars he earned or the blockbuster restaurants he opened in his name. It’s the small stuff that showed his grit and grace. Like calling sick kids in hospitals or showing up at orphanages when the cameras weren’t rolling. He and Dale didn’t just preach family values; they lived them. They took in kids who needed a shot at something better, raised them on good faith and open skies, and put their money where their hearts were when they built the Happy Trails Children’s Foundation to fight child abuse.

Roy didn’t have to be some larger-than-life cowboy when the hat came off. In Apple Valley, California, he and Dale were just Roy and Dale, neighbors who waved from the porch and made the little patch of desert a place that felt like the best parts of the frontier still lingered on. Even when the Roy Rogers-Dale Evans Museum eventually closed its doors in Branson, his legend didn’t pack up with the exhibits. You can still find him in street names like Roy Rogers Drive and Happy Trails Highway, or in the grin of a kid riding a stick horse in the backyard, pretending they’re chasing down bandits with Trigger at full gallop.

Roy passed at 86, and Dale a few years later. They’re buried side by side in the place they loved, leaving behind a trail of songs, stories, and good deeds that still echo every time someone says, “Happy Trails.” In a world that could always use another hero, Roy Rogers remains a reminder that the real kings of the cowboy way ride for something bigger than themselves.

So here’s to the King of the Cowboys, still keeping the campfire burning long after the credits rolled.