Introduction
It was just past 2 a.m. in Cheyenne, Wyoming, during the annual rodeo of Cheyenne Frontier Days — a place where dust still clings to boots and the stars hang low over endless prairie skies. Chancey Williams had finished his set and retreated to his hotel, thinking the night was over. That’s when the phone rang.
“Hey — we’ve got Toby Keith down here,” came the voice on the line. Williams, still feeling the buzz of the stage and the beer, assumed it was a joke. “Put him on,” he said. Then the unmistakable Oklahoma twang answered.
Toby Keith — larger than life, legendary, just off the main stage the next day — said: “What are you doing? Let’s go for a cruise.” It was 3 a.m., but with Toby Keith, time didn’t matter. Boots went back on. Hat pulled down. They loaded into a van. And the ride began.
They rolled through the cleared streets of Cheyenne, laughter bouncing off the highway signs. The problem? They ran out of “cruising beer” at a time when the local stores were long closed. That’s when Toby smiled and said, “I know where there’s beer — Jason, to the airport.”
Moments later, their van curved onto the tarmac at Toby’s private air-strip. The plane sat waiting — lights glowing under its wing like a promise. Inside, Toby had whiskey, more beer, and the kind of private-jet calm that few ever witness. It wasn’t showbiz glamour. It was two men, boots off-duty, drinking on a jet in the early-morning hush.
Williams looked around, realizing: this isn’t just a story. It’s a memory. Toby told him, “If you want, show up tomorrow — we’ll sing ‘Should’ve Been a Cowboy’ together.” Williams laughed, didn’t believe it — but the next day, standing in front of 20,000 people at the rodeo, he did just that.
What this night reveals is more than a party tale. It shows Toby Keith’s spirit: generous, spontaneous, rooted in country life even after the arenas and the fame. He didn’t keep the biggest moments for himself. He invited someone in. He made the ordinary extraordinary.
For Chancey Williams, that ride remains vivid: the darkness of the tarmac, the hum of engines at rest, the clink of bottles, and Toby’s voice — still the same Oklahoma tone, still grounded. In one late-night beer run, he felt what being part of Toby’s world really meant.
When we remember Toby Keith, we’ll recall the hits, the stage, the legend. But maybe the truest tribute is in moments like this — quiet, unexpected, human. A van, a desert airport at dawn, and a private jet that became a living room for a night. Because for a country legend, the real magic was making someone else’s memory.