He graduated in May 2000, and after two auditions began working on two separate projects: the CBS/Alliance mini-series Haven, and director Léa Pool's feature Lost and Delirious (2001).

Soon after, he portrayed Morgan in the Factory Theatre's production of Geometry in Venice in Toronto, a performance that brought him a Best Actor nomination at the Dora Mavor Moore Awards.

Mambo Italiano received a gala presentation at the 2003 Toronto International Film Festival to a standing ovation, and earned Kirby a Canadian Comedy Award Nomination.

In television, one of Kirby's favourite roles was in the TMN/Showcase mini-series Slings & Arrows, featuring Canadian actors and directed by his friend Peter Wellington.

Kirby was nominated for a Gemini Award for his role in Sex Traffic, a mini-series for Channel 4 and CBC that aired in the fall of 2004 under British director David Yates.