Keith Urban Recalls Winning CMA Entertainer Of The Year Over Kenny Chesney The Year After Opening For Him: “It Was Awkward”

How you know you’ve made it big.

Kenny Chesney and Keith Urban are two well-known names in the country music world. Both artists have sold out numerous shows and stadiums and have had long and successful careers, with both men still touring and capturing the hearts of fans. But just like many other country stars coming up around the same time, there is always a sense of competition among those who are rising to fame with you, which can lead to some awkward moments.

Blake Shelton has recently teamed up with Yellowstone creator, Taylor Sheridan, for a brand new singing competition show officially dubbed The Road. Unlike his role on The Voice, Shelton will serve alongside Sheridan as executive producer of the new show, which will feature 12 artists performing on the road with country music superstar Keith Urban. The audience at each show will then help determine which artists continue to the next stop.

Along with Shelton and Urban, Gretchen Wilson will also serve as the “tour manager” for the artists, providing support and guidance as they seek to continue on in the competition.

The “tour stops” took place from March 2nd through April 2nd, including legendary venues like the Ryman Auditorium in Nashville and Cain’s Ballroom in Tulsa, Oklahoma. And yesterday, CBS unveiled the cast of emerging artists who served as Urban’s openers: Adam Sanders, Billie Jo Jones, Blaine Bailey, Briana Adams, Britnee Kellogg, Cassidy Daniels, Channing Wilson, Cody Hibbard, Forrest McCurren, Jenny Tolman, Jon Wood, and Olivia Harms.

The first episode is a little over a month away from airing, with a premiere date of October 19th. With the series premiere nearing, Shelton, Urban, and Wilson are all participating in press to promote the show. In a recent clip shared, Blake Shelton and Keith Urban discuss the early days of their careers.

Remember how we discussed competitiveness at the beginning of this blog? This is where it comes into play. During their conversation, Urban asked Shelton if he had any strong memories of opening for certain artists.

I’m sure Urban was expecting Shelton to share some fond memories looking back on the early days in his career, but instead. Shelton revisited a historical moment, some might say, from Keith Urban’s days as an opening act.

“My favorite thing I was going to say was, Keith Urban was opening for Kenny Chesney. But then Keith Urban won Entertainer of the Year. You know you’re kicking the headliners a** when you win Entertainer of the Year.”

Urban chuckles to himself a little before responding:

“It was an awkward moment…Particularly given that I had voted for Kenny.” 

Blake Shelton burst out into laughter before challenging Urban’s statement about voting for Kenny Chesney.

“Sure you did.”

Kenny Chesney brought Keith Urban on tour as a supporting act numerous times, but this story revolves around a tour they did together in 2004. The following year, in 2005, Urban beat out Kenny Chesney, Toby Keith, Alan Jackson, and Brad Paisley for CMA Entertainer of the Year.

A pretty impressive honor to receive as an opening act.

As the conversation continued, the two then relived some of the people they had both opened for. Blake Shelton shared that he’s opened for Lonestar, George Strait, Toby Keith, Keith Urban, and some other country music legends. He then jokes with Keith Urban that he wishes he had booked him to open for him more.

“In fact, I wish you would book me.” 

Urban, of course, had fond things to say about Blake Shelton opening for him years ago, but today he’s out of Urban’s budget for an opening act.

“Your fees have gone up. Quite considerably. And your backstage rider’s insane.”

HA.

I bet these two have stories for days to swap back and forth, and hopefully get to hear some more during The Road.

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While you’re here, check out the trailer for The Road. It looks like it’s going to be a great series.

The post Keith Urban Recalls Winning CMA Entertainer Of The Year Over Kenny Chesney The Year After Opening For Him: “It Was Awkward” first appeared on Whiskey Riff.