My favorite Western, happens to be a musical to boot. Western + musical = heaven. It's a typical war-time musical, created solely to entertain the troops during WWII.

Here's a great clip from "Riding High". It's Cass Daley, who performs "Willie, the Wolf of the West". The sound quality is not so great, but the movie is from 1943.

Willie the Wolf of the West & He Loved Me Till the All-Clear Came:

Cass Daley - Willie the Wolf of the West (1943) - YouTube

Cass Daley - Till the All Clear Came (1943) - YouTube

Another clip from the same movie, this time with Dorothy Lamour:

Dorothy Lamour - Riding High (1943) - YouTube