How Willingly You Sing revolves around Simon Dore (director Garry Patterson), a young architecture graduate, cartoonist and stage actor. In the guise of an eccentric with an absurd comic view of the world, he appears throughout, whether carrying out his misguided psychiatrist's advice, playing the banjo, being advised by an astrologer, searching for the Wandering Jew who holds the key to the world's salvation, or taking a holiday in the country.