Born of Welsh descent, Watkins was the son of Charles Curtis Watkins II, who was a salesman, while Watkins’ mother was a photographer. Watkins attended Parkway West High school in St. Louis, Missouri and went on to Indiana University with a major in communications with a triple minor in theatre, psychology and French. In the past Watkins worked part-time as a housepainter.
Watkins has done commercials for Miller Beer, the U.S. Navy, Intuit Software, Allstate Insurance, and Snickers chocolate bars. Director Stephen Sommers had given the part of Burns to Watkins because, according to Watkins himself, Sommers liked the way that Watkins sounded when his tongue was cut out.