Chackowicz is a cartoonist and illustrator who received a Harvey Award nomination for his work in Dennis Eichhorn's "Real Stuff." He was a regular on CBC Radio One's comedy program WireTap, writing and performing for the show throughout the length of its run from 2004 to 2015. Chackowicz also plays drums for two long-lived Montreal- based bands: The American Devices (1980) and Nutsak (1996) as has frequently played with Sam Shalabi in projects such as "Land of Kush." He lives and draws in Montreal.