Arguably the most popular book of poetry ever produced in Australia, The Songs of a Sentimental Bloke was first published in October 1915. Its success was immediate and unprecedented for a book of Australian verse. The first edition of 2,480 copies sold out within weeks, and by the end of February 1916 the book had reached a fifth impression and was still selling well. Tongue firmly in cheek, C. J. Dennis informed his publishers Angus and Robertson that the work's 'success [was] becoming monotonous'. There was more monotony to come, however: the book sold more than 100,000 copies in the first five years after its publication, and was rarely out of print in Dennis's lifetime. Added to this, there were film, stage, and musical versions of the work, as well as recitals given by popular entertainers. In many respects, 'The Sentimental Bloke' became a phenomenon of popular culture that took on a life of its own.

Dennis later claimed that the idea for 'The Sentimental Bloke' came from a 'racy' young man from Melbourne he had met in Toolangi. According to Dennis' wife Margaret Herron, the young man had fallen in love with a farmer's daughter, but the farmer disapproved and forbade her from having anything to do with him. The Melbourne man was said to have complained to Dennis, 'what sort of bloke do they think I am? Blimey, anyone would think I was a crook! Ain't a bloke got sisters of his own?' In Dennis's imagination, this frustrated love affair eventually became a story in which a tough, streetwise young larrikin gives up his dissolute ways for domestic happiness with his sweetheart. A crucial factor in the success of Dennis's 'Sentimental Bloke' verse was that it was narrated from the point of view of 'the Bloke', employing a slang idiom appropriate to the character. In his correspondence with his publishers, Dennis noted that 'the stuff, while not having any considerable literary merit, is, I believe, extremely popular'.