The Gol-Darned Wheel and Stetson Hat are in Glenn Ohrlin's book of cowboy songs. The first describes a cowboy's encounter with a bicycle. The second is a tribute to his hat, as you might suspect. For more contemporary songs you might check into anything by Bob Campbell. Some of my favorites are Big Cowboy Moon; Roll On, Cowboys; Round Up Time on the Pitchfork; Arbuckle Coffee, and Dance At Domingo. Also Sonora's Death Row and Marty Robbin's song about Old Red, about the battle between the horse that had never been rode and the cowboy that had never been throwed.