It is impossible for me to pick a single cowboy/western song or singer. The one that I sing most often is Woody's Philadelphia Lawyer but Marty Robbins' collection of Gunfighter Ballads sets the bar! Then you have the old Western movie stars like Gene Autry, Roy Rogers, Tex Ritter, Rex Allan, etc. Wilf Carter (aka Montana Slim) lived the life about which he sang and to a degree Ian Tyson as well. There was just too much great stuff to pick a single preference! Roy Rogers was my cowboy hero when I was a kid and he holds the distinction of being twice inducted into the Country Music Hall Of Fame, once as himself and once as a founding member of the Sons Of The Pioneers. So much great stuff over the years but sadly there are few recording artists today who come even close and that is a pity!