Eyes of a Cowboy (1998)

Lonesome Cooper is a down-and-out country and western singer who travels from town to town - and back in time to the Old West of the 1870s. In both the present and the past, Lonesome has to rely on his singing skills to survive and avoid trouble. While surviving is not much of a problem, avoiding trouble is more difficult, and the time-travelling cowboy discovers that actions he takes in the past have serious consequences - both negative and positive - on the present... and the future.