[1][2] Influenced by American singers Connie Francis, Patti Page and Dionne Warwick,[citation needed] she began singing in talent contests.
It was during a performance at the Glass Bucket Club in Kingston, Jamaica with the group The Vulcans, that Duke Reid's session guitarist Lynn Taitt discovered Dillon.
[1][3][4] While most of Dillon's subsequent recordings would be covers of popular and obscure American songs including Bettye Swann's "Make Me Yours", Perry Como's "Tulips and Heather," The Grass Roots' "Midnight Confessions," and Stephen Stills's "Love the One You're With"; "Don't Stay Away" was an original composition featuring Tommy McCook and the Supersonics as the backing band.
While these early recordings demonstrate Dillon's mastery of the rocksteady sound, a much slower, soulful, response to the sultry weather that made ska's upbeat rhythm and tempo undesirable, even impracticable, it was no indication of her greatest performance, 1967's "Perfidia".
She had a family and career in banking in the United States, flying frequently back to Kingston, Jamaica to continue recording for Reid.