Raymond wrote his three Smiley books (1945, 1947, 1959) in London based on the time he spent as a child in a hot, dusty Queensland small town. He attended the University of Queensland in the 1920s and was working on the Brisbane Mail by 1929 for around five pounds per week.

Raymond went to Britain around 1930 and continued with journalism. He spent time in Spain, reporting for the Daily Express, and moved into theatre and film criticism. He did some song writing and published a few short stories. He was a member of the Press Club, the Chelsea Arts Club, and the Savage Club, frequented by musicians and writers. During the late thirties and forties, he wrote lyrics set to music by various composers.

During the war Raymond was engaged in radio broadcasting to the armed forces and was a film reviewer for the BBC.

Raymond's work was published in Eagle from the first issue, with the western 'Lash Lonergan's Quest' (14/4/1950-14/7/1950) followed by short stories 'The Clue of the Chopsticks' (2/2/1951) and 'He Fell to Fame' (30/3/1951). Other stories appeared in Girl, 'Diana Down Under' (28/12/1951-1/2/1952). His most enduring character, 'Smiley' appeared in Swift as a colour cover strip (9/8/1958-2/4/1960), drawn by Harry Bishop.