Songfacts®:

• Written by Josh Thompson and Brendan Cooney, this desolate ballad flips the script.
  
  It ain't always the cowboy
  That ain't got a lot of hang around
  Ain't got no settle down in their boots
  Gone's just what they do
  
  Usually it's the cowboy who rides off into sunset. However, in this instance, it is the hopelessly free-spirited girl that is not sticking around and is breaking his heart.
• Pardi explained why he recorded the song: "It was just such an anthem for girls and guys, or for the girls trying to do her own things. It's kind of a leaving song, but a happy leaving song. It's about going out to chase her dreams, be independent or do her thing. He ain't mad about it, and I thought that was a really cool outlook of a song and melody; just everything about it was awesome."
• Shot by Carlos Ruiz in Arizona's scenic desert, the video highlights Pardi's love of the West and barrel racing. The clip turns the tables on the typical romantic narrative by showcasing a leading lady who won't be roped down in a relationship.
• Jon Pardi included a second, more cinematic take of the song for the Deluxe Edition of Heartache Medication. Titled "Ain't Always The Cowboy (Western Version)," Pardi pictured the new version in his head as a little movie soundtrack.
  
  "It kinda starts out real intimate," he explained to ABC Audio. "Kind of going with the lyrics, and it kind of builds. And then to where, at the very end, I just see her riding away on the horse into the sunset, and the violins are just playing."