For reasons that are perhaps not yet fully understood by me there seems to be a somewhat classical American cultural trope of the musical cowboy. For some reason the mythical cowboy drifted across the desert on his horse under harsh environmental conditions, fought gunslinger duels, tamed the West, became the sheriff, hung the outlaws, and all this stuff. And yet persistent in the cultural image and musical heritage is the motif of the musical cowboy strumming on a guitar.
Evidence of this construct include the famous Marty Robbins album "Gunfighter Ballads and Trail Songs", and Roy Rogers portraying a cowboy hero on a popular TV show and playing a guitar.
While I may not fully understand the historical basis for the musical cowboy it has occurred to me that in the context of role playing games it would probably be hilarious and a lot of fun to play a "Bard" type character in a Western, Victorian, or Steampunk setting based on the template of a Roy Rogers style cowboy who is carrying around a guitar and always has a "sad, sad song".
Or why not have an anachronistic cowboy character in Shadowrun, and develop a number of Bardic-type spells he could cast by playing a guitar? It would be pretty funny.