David Boswell grew up in London, Hamilton and Dundas, Ontario. He studied film at Oakville's Sheridan College, where he graduated in 1974. After graduating, he tried to earn a living drawing cartoons, and his first full page comic, 'Heart Break Comic' was published in The Georgia Straight. He moved to Vancouver in 1977, and in 1978, he launched the comic 'Reid Fleming, World's Toughest Milkman'.
Based on a childhood bully with the same name, Reid Fleming skirts no aggressive means to sell his dairy products. The series of underground comix was a hit, and in the 1990s Hollywood bought the rights to the screenplay, which has yet to make the silver screen. Another title David Boswell created is 'Ray-Mond'. He is also a photographer and illustrator. A short documentary called 'I Thought I Told You to Shut Up!!' by Charlie Tyrell and Jonathan Demme was released in 2015. It contained contributions by Matt Groening and Marv Newland.