A caller going by the handle "Truck Driver Mark" was looking for a cash prize, so Howard allowed him to play The Homeless Guy Game, explaining that Mark would have to guess if a homeless guy could answer trivia questions correctly or not. 3 out of 5 takes the $500 prize.
What did John Hinckley do? Truck Driver Mark thought the homeless guy would know, but he was clueless: "Really don't know." What does KKK stand for? TDM correctly guessed that the homeless guy would know. What is a marsupial? TDM knew the homeless guy would blow it: "A marsal." What continent is the USA a part of? For some reason, TDM again put his confidence in the homeless guy, who answered: "American continent." On what date is Independence Day celebrated? TDM took the $500 prize by betting the homeless guy would answer correctly.