The Time Keith Urban Outshined His Tour Headliner at the CMAs

Keith Urban and Blake Shelton were swapping stories in a promo for their new show The Road, and Blake couldn’t resist bringing up a classic moment from Keith’s career.

Back in 2004, Keith was the opening act on Kenny Chesney’s tour. Fast-forward just one year, and both Kenny and Keith were up for CMA Entertainer of the Year. The twist? Keith won the night’s biggest honor, while the headliner he’d been opening for walked away empty-handed.

Blake lit up telling the story, clearly enjoying the irony, but Keith admitted, “It was an awkward moment.” He tried to lighten it by joking that he “opened for everybody” back in the day, though by then, the story had already landed its punch.

Something tells us Kenny can laugh about it now.