An energetic, easily likable performer, Widdoes began acting professionally while still in college in a production of "The New Amen Show" at the Diners Playhouse in Lexington, KY in 1974. He made his mark on the New York stage in musicals like the 1977 Equity Library Theatre revival of "Wonderful Town" and the 1982 Off-Broadway show "Is There Life After High School?", for which he earned a Theatre World Award. Following the success of "Animal House", he reprised the character of Hoover on the short-lived ABC sitcom "Delta House" (1979). Widdoes segued into the CBS series "Park Place" (1980), as an inexperienced lawyer, and later was seen as the father of a brood of three who hires Scott Baio as their caretaker in the first and only network season of "Charles in Charge" (CBS, 1984).

After the failure of "Charles", Widdoes moved behind the camera, helming episodes of "Raising Miranda" (CBS) in 1988, and "Just the Ten of Us" (ABC) in 1989. He was given a collection of Dave Barry's columns early in the 90s and decided there could be a series in them. He wrote to Barry and using the Hoover connection from "Animal House" the two struck up a dialogue, which led to "Dave's World".