Dierks Bentley’s Driving, Sheryl Crow is Shotgun

But Who's That in the Backseat?

David Oakleaf got his first taste of fame when he made it to the top five finalists on CMT’s Can You Duet in 2008. And now? Now he’s in the backseat playing sideman to Dierks Bentley and Sheryl Crow.

As Bentley and Crow were driving around Nashville for an episode of Carpool Karaoke, Bentley remarked that everyone in the town was some kind of a musician. That’s when Crow suggested they pick one up to accompany them — physically and musically — during their drive.

Enter Oakleaf. They spotted him walking down Nashville’s Lower Broadway, asked him if he could play in the key of G, and then he got in the backseat and the mini car concert started. The little trio did Crow’s “If it Makes You Happy,” then Oakleaf did one of his own.

Bentley had an epiphany during that song: that this could be a new kind of American Idol, and that if he could turn his driver’s seat around — like the judges do on The Voice — he would.

And if you’re wondering how big of a Crow fan Bentley is, read what happened when she joined him on stage at an ACM show in Vegas in 2013.

Oakleaf said that when he saw Crow, after hearing her yell “Guitar” to beckon him, he was pleasantly surprised. “I started looking around for anyone else carrying a guitar. When I realized she was talking to me, I knew things were about to get interesting,” Oakleaf told People. “I couldn’t see Dierks at first, but when I approached the vehicle, I quickly recognized who was driving. I thought to myself, ‘Only in Nashville…'”

The full Carpool Karaoke episode airs Tuesday at 9 p.m. ET on Apple Music. And Oakleaf’s band The Open Road plays regularly at Nashville’s Wildhorse Saloon.

Alison makes her living loving country music. She's based in Chicago, but she's always leaving her heart in Nashville.