"The Tenderfoot" is a cowboy song with words credited to D. J. O'Malley. D. J. O’Malley was the last survivor of the more than 400 cowboys who attended the first-ever roundup at Miles City, in 1881. In the early 1880s, O’Malley, a boy of 14, had already become "a full-fledged cowboy" as he described himself. O'Malley also wrote the lyrics to "When the Work's All Done This Fall". It was recorded by Jim Kweskin on Unjugged (2018), Oscar Brand on Pie in the Sky and Other Folk Song Satires (1967) and The Best of Oscar Brand (1975).