Shortly before turning 16 and with the help of teacher and music promoter Tony Johnston, Scallon signed with the Decca Records subsidiary label Rex Records. Performing as Dana, Scallon debuted with the single "Sixteen" written by Tony Johnston, while the B-side, "Little Girl Blue", was her own composition. Now studying A-level music and English, she became popular in Dublin's cabaret and folk clubs at weekends, and was crowned Queen of Cabaret at Clontarf Castle in 1968. Rex Records' secretary Phil Mitton suggested she audition for the Irish National Song Contest, due to take place in February 1969 – a victory would see her represent Ireland in the Eurovision Song Contest. With mixed feelings due to nerves she made it through to the final in Dublin where she sang "Look Around" by Michael Reade, later released as her fourth single. Shown live on Irish television, Scallon came second to Muriel Day and "Wages of Love", also written by Reade.