‘What Was Going on Here?’

Blake Shelton and Keith Urban are, inarguably, two of the biggest stars in country music. Both of them have also been grinding it out in Nashville, Tenn., since the late ‘90s.

Shelton, raised in Oklahoma, moved to Music City as a teenager and scored his first hit in the early 2000s with a song called “Austin.” Meanwhile, Urban, who used to front a band called The Ranch, earned his solo breakthrough hit with“But for the Grace of God” in 2001.

Needless to say, both of these heavyweights have been around for a while, which means they have had their fair share of awkward hairstyles that they might regret to this day.

In a hilarious video shared to both Urban and Shelton’s Instagram pages, the two artists look back at some of their regretful growing pains from the past, as part of a promotional video for their new competition series, CBS’s The Road, which finds them serving as mentors.

Blake Shelton Began the Hilarity, Pointing Out a Vintage Photo of Keith Urban

“Do you care to explain this?” Shelton asks, holding up a picture of Urban from years ago, wearing a maroon vest with his hair down to his shoulders.

“Well, that’s what I looked like when I got here, and I couldn’t for the life of me figure out why we couldn’t get me signed,” Urban replied, to which Shelton wanted to clarify if the Aussie was trying to get a “country deal” at the time.

“Yes. I don’t know what the hell was going on,” Urban confessed before returning the favor, presenting an image from Shelton’s “Austin” days. After examining the photo, Urban suggested Shelton borrowed his style from some of the most high-profile American criminals.

“I don’t know when this was, Blake, but you’ve got the Unabomber thing going on,” Urban shared, pointing at the portrait that shows Shelton with long, curly hair. “This is sort of a Charles Manson influence. What was going on here?”

Blake Shelton Named Terri Clark as Inspiration

Letting out a few laughs, Shelton insisted, “There was a little bit of a breeze from behind,” adding, “that was my Terri Clark phase.”

Urban also happened to have found a vintage magazine, given to him by his mother, with both himself and Shelton featured on the cover. He noted that the surprising part of it all was that they were both signed to record labels, despite their slightly embarrassing style choices.

“Was my face two feet across? I think I thought if I grew my hair out and had it come down, it would hide my jowls,” Shelton said of the look he was going for at the time, before Urban added that he thought his picture was pulled from Madame Tussauds wax museum.

“You know you learn a lot when you’ve been on the road for more than a few years…. especially when it comes to your hair.. Right @keithurban??? @theroadcbs #TheRoad,” the hilarious caption reads alongside the post.

All new episodes of The Road air on Sundays at 9 p.m. ET/PT on CBS. New episodes can also be streamed on Paramount+.

This story was originally reported by Parade on Nov 16, 2025, where it first appeared in the News section. Add Parade as a Preferred Source by clicking here.