The only boy of four children, James Maitland was born in Zimbabwe and spent 2 years in South Africa. At the age of seven, James then made the international move with his family to Ottawa, Canada. Maitland was regularly found reciting songs and impersonating others at high school assemblies whenever there was an interruption due to electrical issues in the area. Armed with witty and colorful humor handed down from his parents, Maitland found himself right at home performing improv and sketch comedy skits on various stages in Toronto including the Second City Main stage. These venues were witness to his wide range of characters of different nationalities. Introduced to Monty Python in his early teens, James discovered his love for British comedy and replicating authentic regional dialects in Britain.

Moving to various countries and cultures throughout his life eventually caused a little more stress on his family then ever before. Bouts of ridiculous and obscene performances in front of the family cut the tension and kept the Maitland family closer together. As he puts it, "People take themselves and situations too seriously. Stress is depressing".

With his enormous catalogue of different dialects and facial expressions along side his hard work ethic and self criticism, James is a major comedy force to look out for. His ability and willingness to learn and be put into almost any situation makes him a very huge part of the Fine Line crew.