Keith Urban talks ‘awkward’ interaction with country music legend

Keith Urban recently admitted to an awkward moment he shared with a certain country music legend, which left him uneasy.

The 57-year-old appeared alongside his costar, Blake Shelton, for a promotional video about their upcoming show, The Road, on CBS.

In the clip, Shelton recalled his favorite moment, which still haunts his friend, was the time when Keith beat the country music legend, Kenny Chesney, for an award.

He said, “Keith Urban was opening for Kenny Chesney, but then Keith Urban won Entertainer of the Year [at the ACM Awards].”

The Fighter hitmaker laughed at the memory and replied, “It was an awkward moment, particularly given that I voted for Kenny.”

Notably, the duo’s first show will show behind the scenes of the gritty and unforgiving life of a touring artist. It will feature 12 singers who will open for Keith as the audience votes for their favorite one.

Earlier this year, in conversation with TV Insider, Blake explained, “They [audience] didn't know who was opening. So if they didn't like you, they could walk out, hit the bar, whatever.’

For the unversed, The Road will premiere on October 19, 2025, on CBS.

Is Keith Urban touring in 2025?

Yes, Keith Urban announced his High and Alive World tour in 2025 with dates across North America and Australia. 

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