Howard reclaimed the bit Leno stole for "Jaywalking" by offering a caller the chance to play a round of The Homeless Game. Howard then played clips of Richard asking a homeless guy questions and instructed the caller to guess if the guy would answer correctly.
3 out of 5 takes the $500 prize: What language is spoken in France? The caller correctly guessed that the homeless guy would say French. Who wrote Hamlet? The caller bet against him, but he nailed it: "Shakespeare." How many letters are in the alphabet? The caller correctly guessed the guy would blow it: "22." How many world wars have there been? The caller took the $500 prize by guessing the homeless guy would answer incorrectly: "3."