Howard gave Elephant Boy the opportunity to play The Homeless Guy Game, explaining that Elephant Boy would have to guess whether or not a homeless guy could answer certain trivia questions correctly. 3 out of 5 takes the $500 prize. Spell the word "definitely." Elephant Boy correctly guessed that the homeless guy would blow it: "D-E-F-I-N-E-T-I-N-R-L-Y." What branch of the armed forces uses the initials USMC? Elephant Boy again got it right, this time predicting that the homeless guy would know the answer. Who is the Mayor of New York City? Elephant Boy bet against the homeless guy, who actually got it right: "Mayor Bloomberg." What century is this? Elephant Boy incorrectly predicted that the homeless guy would know: but he answered, "20th century." How many world wars have there been? Elephant Boy again bet on the homeless guy--and lost: "Oh, thirty--thirty five." Howard let Elephant Boy have the $500 prize anyway.