Dillon was born in 1944 in Linstead, St. Catherine, Jamaica, and attended the Linstead Primary School. Influenced by American singers Connie Francis, Patti Page and Dionne Warwick, 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 sessionguitaristLynn Taitt discovered Dillon. Dillon recorded her first record for Duke Reid, "Don’t Stay Away", in late 1966, a recording that has been described as "perhaps the finest female performance in Jamaican music". 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. Another original song, "It’s Rocking Time" would later be turned into the Alton Ellis' hit "Rocksteady". 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". Popularized by the American surf rock bandThe Ventures, "Perfidia" is a 1940 song written by Alberto Domínguez and made popular by the Cuban bandleader, Xavier Cugat. Dillon also recorded duets with Ellis, including "Why Did You Leave Me To Cry" and "Remember that Sunday". Dillon is regarded as one of the key singers of the rocksteady era. At the end of 1967, Dillon moved to New York. The following five years, she spent living a double life. She had a family and career in banking in the United States, flying frequently back to Kingston, Jamaica to continue recording for Reid. After a number of singles and an album entitled Living in Love, Dillon ended her recording career in 1971. In 1991, Michael Bonnet, the entertainment director for the Oceanea Hotel in Kingston approached Dillon inviting her to sing. Her refusal at first was later rescinded and sparked a revitalized interest in performing and recording. In the years following, Dillion would tour the UK, Germany and Japan. In 1998 Phyllis Dillon returned to the recording studio with Lynn Taitt, marked by reinterest in ska music in the United States. She remained active until illness took hold. Phyllis Dillon died on 15 April 2004 in Long Island, New York, after a two-year battle with cancer, at the age of 59. Dillon was posthumously awarded the Order of Distinction in 2009 by the Jamaican government.
