Keith Urban can light up any stage, but one time his star power made things a little tricky.

While promoting his new show, The Road with Blake Shelton, Urban looked back on his days as an opening act and remembered one particular tour with Kenny Chesney. The year was 2004, and Chesney was the reigning stadium king while Urban was the rising star just grateful for the slot. Then came the twist. A year later, Urban walked out of the CMA Awards as Entertainer of the Year. The opener had just won country’s biggest crown while the headliner went home empty-handed.

Blake Shelton, who loves stirring the pot, could not resist retelling the story. “Keith Urban was opening for Kenny Chesney, but then Keith Urban won Entertainer of the Year,” Shelton laughed. “You know you’re kicking the headliner’s ass when you win Entertainer of the Year.”

Urban chuckled but admitted the whole thing felt a little off. “It was an awkward moment,” he said, before adding with a grin, “Particularly given that I voted for Kenny!”

That is Keith. Smooth as butter, humble to the core, and sharp enough to know how wild that moment really was. In country music, the Entertainer of the Year award is more than just a trophy. It is a torch. It means you have proven yourself as the act who can pack arenas, sell records, and bring the fire night after night. To win it while you are still the guy playing the opening set is almost unheard of.

Even so, Urban never let that moment sour the friendship. Chesney brought him out again for later tours, and the two have stayed tight. That says everything about Chesney’s confidence and Urban’s humility. There was no ego battle, only mutual respect between two artists who know the grind.

Urban has been around long enough to understand what it is like to hustle for attention. During their conversation, he reminded Shelton that he once opened for a comedian, of all people. “Come out and play for 30 minutes to an audience that wants to see a comedian,” he said. That audience doesn’t want to see a singer, so you learn a lot about how to keep that audience engaged.”

That determination is exactly what is fueling The Road, the new reality competition series Shelton and Urban are bringing to CBS. The show will throw 12 up-and-coming artists into the deep end, opening for Urban in real venues with real crowds who get to decide if they have the goods to keep riding the bus. As Shelton put it, “Keith’s fans came to see him. They didn’t know who was opening. So, if they didn’t like you, they could walk out, hit the bar, whatever. That’s as real as it gets.”

The irony is not lost here. Urban once stood side stage, hoping Kenny Chesney’s fans would stick around for his set. Now he is the headliner with the power to hand that same opportunity to a new generation. Unlike the comedian crowds or the awkward CMA win, these rookies will have Urban cheering them on every night.

Back in 2005, it was an awkward moment. In 2025, it looks a whole lot more like destiny.