SHOCKING TWIST: Keith Urban Admits Awkward Moment Touring With Kenny Chesney — Before Beating Him for Country’s Biggest Prize

Keith Urban can own any stage, but even superstars have moments that feel a little… off. While promoting his new CBS show The Road with Blake Shelton, Urban looked back on his early touring days — and revealed one unforgettable, awkward twist involving Kenny Chesney.

The year was 2004. Chesney was the reigning king of stadium tours, packing arenas night after night. Urban? He was just the rising star, thrilled to have a slot as Kenny’s opener. But then, just one year later, everything flipped. At the CMA Awards, the “opening act” walked out as Entertainer of the Year — the single biggest crown in country music — while the headliner went home empty-handed.

Blake Shelton, never one to miss a punchline, couldn’t resist stirring the pot. “Keith Urban was opening for Kenny Chesney, but then Keith won Entertainer of the Year,” Shelton laughed. “You know you’re kicking the headliner’s ass when you win that.”

Urban chuckled at the memory, but admitted the moment was “awkward.” Then came the kicker: “Particularly given that I voted for Kenny!” Smooth, humble, and sharp — classic Keith.

In country music, Entertainer of the Year isn’t just a trophy. It’s a torch — proof that you can pack arenas, sell records, and bring fire night after night. To win it while still playing the opening slot? Almost unheard of.

Yet, instead of tension, there was respect. Chesney invited Urban back for later tours, and the two remain friends. No ego, no feud — just two legends who know the grind.

Urban even reminded Shelton that before those big stages, he once opened for… a comedian. “Play for 30 minutes to an audience that wants to laugh, not hear a singer,” he said. “You learn a lot about keeping people engaged.” That grit is what shaped him — and now fuels The Road, where 12 new artists will face real crowds, real pressure, and real judgment.

The irony isn’t lost: once the nervous opener praying fans wouldn’t walk out, Keith Urban is now the headliner giving rookies the very chance he once fought for.

Back in 2005, it was awkward. In 2025? It looks a whole lot like destiny.