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James Whittingham was born in Fort Frances, Ontario, and raised in Regina, Saskatchewan where his life as an improvisational comic actor began after landing the role of The Big Bad Wolf in a Kindergarten puppet show production of "Little Red Riding Hood." James improvised puppet shows for neighborhood kids until he starting making films at age twelve. In high school and University Whittingham performed comic roles at the local cable TV station and in student and independent films before graduating with a BFA in film production from the University of Regina in 1992. Whittingham then teamed up with Kevin Allardyce in Regina for a local cult TV show, The James and Kevin Show. In 1997, after working with comic mentor, Dan Redican, Whittingham and Allardyce had starring roles on CBC Television's Just for Laughs in that season's interstitial segments. The duo continued to develop shows for Canadian Television before parting ways professionally in the early 2000's. Whittingham experimented with comic blogs, podcasts and YouTube in the 2000s while working on other television pilots and independent films in Saskatchewan, including regularly working with director Lowell Dean (13 Eerie, Wolf Cop). Whittingham made his feature film début in Brian Stockton's (et al) I Heart Regina in 2010. He continues his work with Stockton in the upcoming feature comedy, The Sabbatical.