A caller named Mark needed some money to pay for his dog's eye surgery, so Howard allowed him to play a round of The Homeless Guy Game, explaining that he'd read five questions and Mark would have to guess whether a homeless man had answered them correctly. Three out of five takes a $500 prize.
On which day is Independence Day celebrated? Mark incorrectly guessed the homeless guy would know the answer. The bum slurred: "July 14th." How much is 3 cubed? Mark bet against the bum again, this time for his first point: "3 cubed is 9 feet." What is 50% of 500? Mark didn't think the bum would know, but he was ready with the answer: "250." What is Batman's secret identity? Mark got his second point when the bum answered: "Bruce...uh, Bruce Jackson." Cleopatra was from what country? The bum nailed this one ("Egypt!") - shooting down Mark's hopes - so Howard allowed Mark one more chance: What do the letters FDA stand for? Mark said there was no way the bum would know, and, like usual, the homeless guy confused "Food" for "Federal."