Prior to working for CBC Radio, he was a writer for the Canadian TV show This Hour Has 22 Minutes.
[1] From 1993 to 1996, Shigematsu wrote and performed his one-man show Rising Son in Montreal, Boston, Los Angeles, and Tokyo.
His video work has been seen in the Montreal World Film Festival and the Biosphere and won the Prix du Public at the Evénement Interuniversitaire d'Art.
In 2009, Shigematsu appeared in Episode 2 of the TV series Deadliest Warrior as one of the experts for the Samurai team.
He conducts research on social media, with a focus on the rising visibility of diasporic Asians on YouTube, for which he was named a Vanier scholar.
The entire run sold out prior to opening, an unprecedented feat for the world premiere of a Canadian play,.
In October 2017, Shigematsu's next solo work, 1 Hour Photo, had its world premiere at The Cultch in Vancouver.