Crosby had recorded cowboy songs for the first time in 1933 and he had a huge hit with "The Last Round-Up" that year on the Brunswick label.

Commenting on these early recordings, the writer Gary Giddins said "…it anticipated the golden age of gentle-voiced singing cowboys and the Irish sentiment of John Ford westerns that followed on their heels.

"[1] Moving on to the Decca label, Crosby had huge hits with "I’m an Old Cowhand", "Empty Saddles" and "Mexicali Rose".

He also charted with "My Little Buckaroo" and "There’s a Gold Mine in the Sky".

Giddins considered Bing's recordings in his book[2] saying: "The most impressive of his new cowboy songs (including "We’ll Rest at the End of the Trail", "A Roundup Lullaby", "Empty Saddles") was "Twilight on the Trail", a lament introduced that year by Fuzzy Knight in The Trail of the Lonesome Pine and sung by Bing as though it were an old western hymn.