Richard Killeen attended the University of Auckland’s Elam School of Fine Arts, graduating in 1966. In 1967, he began work as a part-time sign writer and first exhibited at The Group Show, Ōtautahi. His work was included in New Zealand Art of the Sixties at the Auckland City Art Gallery (now Auckland Art Gallery Toi o Tāmaki).

In 1975, Killeen won the Tokoroa Art Award and travelled to Sydney and Melbourne. In 1976, he won the Benson & Hedges Art Award. A QEII Arts Council travel grant enabled him to visit Europe and the United States of America. In 1981, he began working as a full-time artist and in 1982 his work was included in the Biennale of Sydney. In 1984, he travelled to the Edinburgh Festival, spending time in Italy, Morocco, New York, and Brisbane.

Killeen is well known outside New Zealand, having had shows in New York, Sydney, Chicago, Paris, and Spain. He was one of the ‘New Image’ painters of the 1980s, included in the show of that name curated by Francis Pound. Known today as post-modernists, the participating painters reintroduced images into their work as a reaction against the abstract or expressionistic modernism of the previous generation.