Richard Herring: The Headmaster's Son (2010) is a Comedy film that follows in The Headmaster's Son, a nostalgic and faintly disturbing juvenile romp through the 1980s, Richard Herring considers what could possibly be worse than being a podgy, swotty, virginal schoolboy. What if your dad's the headmaster too? Richard Herring: The Headmaster's Son is not currently listed with streaming providers in your selected region, but availability can change over time. It has a user rating of 6.7 out of 10 from 3 votes. Fans of comedy movies may also want to explore similar titles below.