Having recorded the original version of the Bob Dylan co-penned song "Wagon Wheel," which hit #1 on the Country charts when covered by Darius Rucker, the legendary songwriter provided Old Crow Medicine Show with another demo for their Remedy album. Frontman Ketch Secor explained to CMT: "We got an email from Bob Dylan's manager saying congratulations right around the time Darius Rucker had a #1 single with 'Wagon Wheel.' It's not every day that country music recognizes this great pioneer and huge influence, Bob Dylan. Bob doesn't have many #1 songs in any genres. So it was a big deal to get one."
Secor added: "A couple of weeks later, he sent a demo and said, 'Here's a song that I never really finished. It was recorded a few days after 'Rock Me Mama.' Give it a try. We'd like the boys, the Old Crows to give it whirl.'"
That song turned out to be "Sweet Amarillo" from the sessions for Dylan's 1973 Pat Garrett & Billy the Kid soundtrack album. "I was working with about 26 seconds in which there's a lot of giggling in the background and it just sounds like a pretty high time down in Monterey, or Durango, or wherever they are making this Western movie," Secor explained to The Associated Press.
Secor finished the song with Old Crow Medicine Show turning it into a waltz about a cowboy's search for his lover and sent it back to Dylan. "He said, 'Hey, that sounds great, but I think Ketch should play the fiddle, not the harmonica, and I think the chorus needs to come in at the eighth bar, not the 16th.'" recalled the frontman "We did exactly what Bob said, and it's like the song sprouted wings and flew."