James Whittingham was born in Fort Frances, Ontario, and spent his childhood in Regina, Saskatchewan, where his journey as an improvisational comic actor began. He landed his first role as The Big Bad Wolf in a Kindergarten puppet show production of "Little Red Riding Hood" and went on to create improvised puppet shows for neighborhood kids. This early start in the world of comedy sparked his passion for performance, and by the age of twelve, he began making films.
Throughout his high school and university years, Whittingham honed his comedic skills by performing in local cable TV shows, student films, and independent projects. He graduated from the University of Regina in 1992 with a Bachelor of Fine Arts in film production. Whittingham then teamed up with Kevin Allardyce in Regina to create a local cult TV show, The James and Kevin Show, which gained a loyal following.
In 1997, Whittingham and Allardyce landed starring roles on CBC Television's Just for Laughs in the interstitial segments that year. The duo continued to develop shows for Canadian Television before parting ways professionally in the early 2000s.
In the 2000s, Whittingham experimented with comic blogs, podcasts, and YouTube, while also working on other television pilots and independent films in Saskatchewan. He regularly collaborated with director Lowell Dean, who is known for his work on films like 13Eerie and Wolf Cop.
Whittingham made his feature film debut in Brian Stockton's I Heart Regina in 2010 and has continued to work with Stockton on upcoming feature comedies, including The Sabbatical.
