“Do you find that people just cannot figure out how to spell your name?” Crow asks Bentley in a sneak peek of the latest edition of Carpool Karaoke streaming on Apple Music and shared exclusively with PEOPLE.
“Yeah,” replies Bentley.
“I get Sheryl with a C,” admits Crow, 55. “It’s not?” teases Bentley, 42, before the pair go around quizzing people to see if they can spell their names. (Spoiler alert: no one gets their first names right — and most want to add an “e” to Sheryl’s surname.)
In addition to spelling pop quizzes, the pair also picks up a local musician, David Oakleaf, while they’re out-and-about.
“Hey, hey, guitar!” Crow shouts at a man walking down the street before inviting him to jump in the back of the car where the trio sings Crow’s hit “If It Makes You Happy”—and Oakleaf even shares one of his own tunes.
“If I had the button to push to turn my seat around, I’d be like …’” says Dierks referencing the reality singing competition series, The Voice. “You’re great! You’re good, man.”
“Being on Broadway, I figured it was bachelorette party on a pedal tavern rolling by at first,” Oakleaf tells PEOPLE exclusively of the experience.
He continues: “When I turned around and saw Sheryl Crow, I 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. 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…'”
Bentley and Crow’s full Carpool Karaoke episode airs Tuesday at 9 p.m. ET on Apple Music.
- Reporting by SARAH MICHAUD