Harold Middleton was schooled at Brisbane Grammar during the latter stages of R.H. Roe's tenure as Headmaster (1876-1909). During his youth he developed a passion for music, eventually developing his skills as both a musician and composer. After leaving school he joined the staff of W. H. Palings, spending quite a few years at their Sydney store. Middleton is known to have still been in Sydney in late 1921, with his name being identified with Palings second Australian Compositions concert held at the firm's Sydney concert hall on 16 November that year. He performed a musical monologue by William Shatton.
By 1923 Middleton had returned to Brisbane, possibly to work at Palings store. In September that year he won second prize in a competition run by the
Queensland Figaro calling for essays on the subject of opposing prohibition. The article, titled 'The Speciousness of Prohibition,' was published in the paper's 13 September edition. Around this time Palings published his song 'Calling Coo-ee.' The number featured in his pantomime,
Hop O' My Thumb, which was staged at the Cremorne Theatre over the Christmas/New Year of 1924/25 by the Famous Diggers. Middleton's association with Hanna saw him also write at least one comedy sketch for the Famous Diggers - 'The Besieged.'
The mid-1920s also saw Middleton appears as both performer and accompanist at various Brisbane social events. One such occasion was the Caledonian Society and Burns Club entertainment produced at the Theatre Royal on 24 January 1925. Three years later he produced another pantomime,
Puss in Boots, which was staged at the Sandgate Town Hall by members of the local community.
Among Middleton's other known words are the songs 'Bring Along the Girls' (co-written with E.T. Shorley) and 'Song of the Convoys.'
[Source:
Australian Variety Theatre Archive]