Chester Brown became involved in the production of comics in his early twenties, submitting works to Fantagraphics, Last Gasp, and Raw. He began to self-publish minicomics under his Tortured Canoe imprint in 1983. This lead to the initial publication of Yummy Fur, which ran for seven issues and brought him recognition in the small press scene, as well as some commercial success. Yummy Fur was officially picked up as a bimonthly title by Vortex Comics in 1986, which allowed Brown to dedicate all of his time to creating. Around this time he began producing the surreal, darkly humorous Ed the Happy Clown, the content of which drew some efforts at censure by publishers and distributors, some of whom refused to publish his works. He also began work on the first of his Gospel adaptations, producing a comic adaptation of the Gospel of Mark, the religious themes of which he would continue to pursue through numerous other adaptations of scripture and apocrypha.
He moved on from his fictional works in the late 1980s and early 1990s, beginning work on a series of more personal autobiographical works. His art evolved as he attempted to distance himself from the art and style of Ed. This produced short works such as "Helder" and the reflexive, deconstructionist "Showing Helder", as well as longer works, such as the graphic novel The Playboy. This period marked his move to Drawn & Quarterly, who began publishing his work with Yummy Fur #25. Concluding his autobio interests in 1993 with the story that would become I Never Liked You, he began work on an ambitious experimental comic detailing the acquiring of language, called Underwater, that he ultimately left unfinished due to the difficulty of the project, and negative reviews. He began work on Louis Riel, an adaptation of the life of the historical Canadian figure of the same name, in the late 1990s.
Around this time he began work on a new autobio comic, Paying For It, which would not be published until 2011. During most of the 2000s he produced very little, instead allowing the reprint of Ed comics, doing annotations and explanatory notes for his works, and producing a few comics for NOW magazine.
Chester Brown was born in Montreal, and raised in the English-speaking Châteauguay suburb of that city in a strictly religious household. He moved to the city of Toronto at the age of 19, and has resided there for most of his adult life, barring a brief period living in Vancouver. Aside from comics, he has shown a deep interest in politics; he ran as the Libertarian Party of Canada's representative for the Toronto riding of Trinity-Spadina in 2008 and 2011.
He is close friends with fellow artists Seth and Joe Matt. He is outspoken about his disinterest in traditional romantic relationships and frequenting of prostitutes.