Drew Klassen was born in Toronto in 1964, (mis)spent his youth in Winnipeg, and in 1986 went to Halifax to study drawing and sculpture at the Nova Scotia College of Art & Design. Following NSCAD, he taught himself to paint while supporting himself by varied means. While teaching English in Japan, Klassen began to exhibit his work, and on his return to Canada in 1998 he established a consistent studio practice and began to exhibit regularly in Canada.

From 20012007 he taught representational methods and theory at the Dalhousie University School of Architecture, and from 20062010 he taught painting at the Nova Scotia College of Art and Design. His work is held in numerous private collections in Canada and abroad, and in a number of corporate and institutional collections, including the Art Gallery of Nova Scotia. In 2010 he received one of five Established Artist Recognition Awards presented annually by the government of Nova Scotia.