Now, the artist, occasional musician, amateur letter-writer and professional provocateur has collected some of his portraits of Toronto's citizens -- from high-profile tastemakers to neighbourhood characters -- in the new book, Joe's Toronto.

Populated by the city's "famous, infamous and unknown," the book includes images of everyone from Annex resident Margaret Atwood to Katherine Goldberg, the former Filmores stripper who lobbied against lap dancing, to Max, the newborn son of one of Mr. Joe's frequent models. From his 1984 painting of musician Colin Linden to his recent portrait of rape victim turned crusader Jane Doe (albeit in profile, her face obscured by a cowboy hat), the collection spans two decades and represents only a small fraction of Mr. Joe's estimated 500 portraits.

As much as the book is a mosaic of the city's citizens, it's also a reflection of Mr. Joe's own life and interests. Born and raised in Maple, Ont., he made Toronto his base while he established himself in the mid-sixties as a folk-blues musician in the band McKenna Mendelson Mainline. He began painting a decade later. Painting acrylic on canvas, he calls his style "attempted realism:" flat patches of colour, whimsical lines and an unfearing eye.

It has since become a badge of honour for politicians and journalists to receive a postcard of one of his pieces with a message, either withering critique or bombastic praise, scrawled on the back.

It's not a surprise, then, that Joe's Toronto includes John LaRocque, the owner of Ring Music on Harbord Street, which Mr. Joe frequented during his musician days, or Cathy Crowe, the nurse and activist for Toronto's homeless, whom the painter calls a hero.

Other portraits made their way onto his canvases and into the book because they represented "important cogs in the wheel." Nobody's face has been transposed onto a questionable body part, but that doesn't mean Mr. Joe endorses the views of all those he has painted.

Count political activist Irshad Manji among that 5 per cent. The author of The Trouble with Islam: A Wake-Up Call for Honesty and Change says she was daunted when he first approached her. She was determined to go through with the sitting, however, in order to learn from Mr. Joe, whom she sees not simply as a chronicler of Toronto's citizens but as a role model.

Ms. Manji notes that few cash-strapped artists like Mr. Joe spend time and money writing to politicians and public figures to critique their views. She also admires how he encourages his female friends to take self-defence courses by bribing them with one of his works.

This is cache, read story here