In the 1950s Shirley Simmons started out as an office typist. Bored with her job, she quit and started singing. In no time she got nightclub jobs all over Sydney and was heard on radio and appeared on TV like Johnny O'Keefe's Six O'clock Rock. She also toured South East Asia singing in stage shows in Hong Kong and Singapore. She recorded on the Festival label. Shirley also did seven tours of Vietnam from 1964 to entertain the troops.