The opening of the Columbia pressing plant in 1926 with its brand new technology of electrical (as distinct from purely acoustic) recording opened the doors to Australian performers to record their music. Columbia’s Sydney-based factory was followed within a year by Vocalion Records opening a pressing facility in Melbourne. One of the first local recordings was O! Sydney I Love You, the winner of a song writing competition organized by The Sun newspaper. On 16 March 1927 the paper enthusiastically reported on the recording session, with Len Maurice and the 2FC Studio Dance Band led by Eric Pearse recording the song.

The NFSA has five separate versions of the song, including another by Len Maurice just with piano accompaniment (Columbia 0611), perhaps recorded at the same session.