In this Radio.com interview, he discusses writing the song. Stapleton's wife bought him a 1979 Cherokee Jeep, and they flew out to Arizona to pick up the car. Instead of having it shipped home, they drove it back to Nashville.

It was a risky idea, he allows, given that the car is over three decades old. They also decided to film their trip, with no real reason to do so. "We were just going to do it to do it, which is the best reason to do things, because you feel led to do them."