Drummond's career began in pubs in Sydney in the late 1970s and early 1980s, where he performed musical mini-operas in a folk rock style that included sections written for audience participation.
Drummond was subsequently invited by his friend Roger Corbett to join the revived Bushwackers, before forming a duo with John Schumann after supporting Redgum on a national tour.
Drummond then toured across Australia staging fundraising concerts for community-based organisations, schools, preschools, toy libraries, church groups and service clubs.
In 1998 he began an association with The Naked Poets, a group of five comedic Bush Poetry performers: Marco Gliori, Shirley Friend, Murray Hartin, Ray Essery and Bobby Miller.
Produced by Rod Coe, "Six Days in December" saw them pick up the 2001 award for Contemporary Country Song of the Year with a duet called "The Rush", which had already won two sections of the Queensland Songwriting competition.
With fellow songwriters, Tony Williams and Chris O'Leary the show was set around three old mates who meet at a BBQ after not having seen each other for nearly a decade, and uses comedy to explore the middle aged male condition.