Willson was raised in Paris, Ontario. Willson had learned techniques of acting. Later he founded Willson Entertainment Productions. In 2010, Matthew starred in a feature-length movie "Skinning the Cat". Matthew also appeared in "The Negotiation" in 2015. In 2016, he played a role in "Arrival" along with Amy Adams and Jeremy Renner. Matthew also appeared in Canadian Comedy Awards and several TV movies.