"The Sunny Side of the Mountain" certainly turned out to be a popular location for country and bluegrass performers; it's one of the best-known co-writing ventures of Bobby Gregory, a performer and bandleader as well as songwriter whose career in the '20s, '30s and '40s spanned the genres of Tin Pan Alley and country & western. The man is wearing a cowboy hat on the cover of Bobby Gregory's Jumbo Song Folio Number 10, and he led a band called Bobby Gregory & His Cactus Cowboys, whose vintage reissue on the Cactus label is proof -- if the label's hype can be believed -- that the man "belongs to the more important figures of country music history!"
The preceding quote, worded somewhat awkwardly as it is, makes it sound as if Gregory was some kind of a man-slave for Hank Snow. In reality, his output cannot even be said to belong exclusively to the country genre, He came from a generation of performers to whom sentimental, so-called cowboy songs -- many of them managing to bring forth an even larger flood of tears than country & western hits -- were an important part of the overall pop songwriting scene. One of Gregory's most successful collaborators was performer and songwriter Vernon Dalhart, who after performing opera among other vocal traditions, began pumping out ballads with as Western a flavor as a bowl of Cookie's famous cowboy stew. Gregory could also pump, supposedly helping write between 1500 and 2000 songs depending on who is counting. As a recording artist he may have cut as many as 350 titles on a dozen labels. Ownership of his masters was apparently scattered hither and yon, a challenge that Cactus took on in order to provide interested listeners with an alternative to scrounging old collections of 78s. The sides cut by Gregory and his outfit of course come out of the connected cowboy, hillbilly and hobo modes, and include "She's Only a Moonshiner's Daughter," "Cowgirl Polka," "Cowboy Rag," "Cryin' Hobo," "Yodelin' Hobo," "The Hungry Hobo," and "The Sagebrush Waltz." Gregory's songwriting credits lead to genres in which suit and tie, not hat and spurs, were the normal on-stage attire. Tommy Dorsey recorded "Am I Dreaming," a collaboration with record producer Joe Davis and bandleader Charles Dornberger. Gregory shows up as a bandmember in some of cowboy star Roy Rogers' movies.