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Will has acted in the feature films Witless Protection, Stranger Than Fiction, Something Better Somewhere Else, Camp Manna, B-Roll, After Effect, No Sleep 'Til Madison, Stash, and Serious Business, as well as the short films Stealing Kisses, Hit and Run, Rain, Rain, and Train Town (which won a Silver Award at the Chicago International Film Festival and a Best of the Midwest award for Best Short Film). Will's work in Train Town was nominated for a BMA Award for Best Actor. He wrote, directed and starred in the short film William Flugle's Travel Adventures with William Flugle; it was an official selection at the Monmouth Film Festival, the Chicago Comedy Film Festival and the Chicago International REEL Shorts Festival, where it was named Best Comedy. He also wrote, produced, co-directed and starred in the short film The Calvin Lewis Bobby Mayfair Show[s] (Audience Award, Chicago Comedy Film Festival).
Will has appeared in a number of network and cable television shows, including Chicago P.D., Sirens, Play by Play, ER, Early Edition, America's Most Wanted and The Untouchables. He is a recurring character in the fourth season of Fargo. He produces and hosts the TV series Wild Travels on PBS, and his work on the show has earned him a Midwest Emmy Award. Previously he was the host and segment producer of Wild Chicago, for which he won fourteen Midwest Emmys.
