[2] Before joining SFFILM, Cowan was the artistic director of TIFF Bell Lightbox,[3] and also worked as the co-director of the Toronto International Film Festival from 2004 to 2008.

Titles distributed by Cowboy and Code Red included: The Life And Times Of Hank Greenberg, Fat Girl, George Washington, La Cienaga, Promises (nominated for Best Documentary at the 2002 Academy Awards)[9] and The Endurance: Shackleton's Legendary Antarctic Expedition.

Cowboy also acted as a releasing sub-distributor for Miramax Films, bringing to market their Rolling Thunder titles acquired in collaboration with Quentin Tarantino.

In partnership with The Museum of Modern Art, the foundation funded, acquired, distributed and created educational material for socially meaningful cinema from the developing world.

Cowan was the Toronto curator for several exhibitions including Tim Burton (a project of the Museum of Modern Art, New York) and Fellini: Spectacular Obsessions (which premiered at the Jeu du Paume in Paris in 2009).

He contributed to catalogues for both shows, oversaw an Alternative Reality Game (Body/Mind/Change, created by Lance Weiler) and the David Cronenberg Virtual Exhibition.

He successfully moved SFFILM Festival's theater footprint to transit-friendly neighborhoods, resulting in a significant shift to younger and more diverse audience demographics and doubled foundation support for artist development activities, initiating unique new programs with Alfred P. Sloan, Westridge, Flora Family, Compton and Time Warner Foundations, He also launched SFFILM Invest, a major initiative to bring philanthropic and equity-based investments to contemporary American independent films; initial slate generated $1 million in investments.

Cowan had worked as an independent consultant to film festivals, movie theaters, producers and media-related NGOs from October 2019.