Unsatisfied with the What's Older Than Ronnie? game, Howard offered another caller the chance at The Homeless Lady Game. The caller will have to guess whether or not a homeless lady would answer trivia questions correctly – 3 out of 5 takes the cash prize.
The caller bet against the homeless lady each time.
The questions, followed by the homeless lady's answers: Who sailed to the Indies in 1492? "Well, Columbus was sailing, but I don't know where he was sailing. Ok?" How many days are in a year? "29 days." What branch of the military is the USMC? "Usually, they Army." An octagon has how many sides? "Usually 8." How many World Wars were there? "So far that I recall, we had two World Wars." Howard gave the guy the money anyway.