Hewitt began working in the entertainment industry as a teenager, on television series for the CBC and YTV.
[2] Jimmy was the boyfriend of Scott Pilgrim's sister before being seduced by Pilgrim's roommate Wallace at a "Crash and the Boys" (a fictional version of Toronto band Broken Social Scene)[3] concert and appearing in recurring gags with Wallace.
[5] In 2018, he starred in the YouTube web series Clusterfuck, which follows the lives of millennials in downtown Toronto.
Hewitt won the Best Actor award for his role at the Sicily Web Festival, where the series was given a premiere,.
[6] Hewitt has starred most prominently in works with a strong Toronto identity: Scott Pilgrim vs. the World, This Movie Is Broken, and Clusterfuck.