Jolly was born on Broughton Island. He now lives in Pangnirtung with his wife and four children.

Jolly has been printmaking for over ten years. He studied at the local learning centre of Nunavut Arctic College (woodcuts) and then went to Iqaluit with his family for more printmaking courses. There, he studied etching, watercolour for printmaking, stencil, oil painting, silkscreen, and also a visual fine art and craft foundation course.

After completing his diploma in 1994, Jolly joined the Uqqurmiut Centre for Printmakers in Pangnirtung. He has been busy ever since, painting and printing, teaching printmaking, and attending arts festivals across the arctic.

During the winter of 2001, Jolly attended a jewellery course at Arctic College. His natural talents as an artist transferred easily to working in metal, and he enjoys the challenge of a new medium.