John Gillies studied figure drawing under sculptor Tom Taylor at St Andrew's College, Christchurch and developed a special interest in portrait painting as a secondary school student. Later, when training as a medical student at the University of Otago, including two years in the anatomy department, John realised this learning experience would be invaluable for his intended art career in later life. He went on to dabble in landscape paintings, and his first solo exhibition of these works was at Abernethy's Gallery in Dunedin. When he moved to Christchurch in 1980, John became an artist member of the Canterbury Society of Arts and contributed work for exhibitions as an invited guest on a regular basis with Fisher Fine Arts.
He has gone on to win awards with his work including:
- Highly Commended, Telecom Art Award, 1992
- Highly Commended, Montana World of Wearable Arts Award, 1998
- Winner, Creative Excellence Award, NZ Association of Artist Doctors, 2005
- Section Winner, Montana Wearable Arts Award, 2005
- Winner, Painting Award NZ Association of Artist Doctors, 2006
His work is held in both corporate and private collections and he has been commissioned for portrait painting by the University of Otago, Princess Margaret Hospital, The Christchurch Clinical School of Medicine, St Andrews College and the Isaac Theatre Royal Trust. His portrait work was accepted in the Biennial Adam Portrait Award and his painting of Col. Bob Upton was selected for the "Double Exposure 3" exhibition in Wellington in 2007.