Q: A car is parked outside of a hotel, it drives off and the guy ends up in jail. How?
A: Its a monopoly game board.
My informant first heard this riddle when he was 8 years old. My informant and some of his friends were playing monopoly and after they were done playing the game, my informants friend told this riddle. Since my informants friend told this riddle right after playing the game board, my informant was able to get the answer. However, when my informant told this riddle at the barbeque we were all confused and none of us could get the answer.
After all of us heard the answer to the riddle from my informant, all of us thought that it was a silly riddle because the answer was so simple. Most riddles have this effect because when most people think about riddles, most people try to overanalyze it by thinking of different situations. When most people tell riddles, it is automatically thought in peoples minds that the answer will be hard to get or it will be tricky. Since most people automatically have this mindset, the riddles that are the hardest to answer are actually the simplest riddles. The simplest riddles are the ones that get people the most. This is why most people tell these types of riddles because once the person realizes how easy the answer was, they feel dumb. Therefore, the person telling the riddle finds it amusing or entertaining that the person is trying so hard to figure the riddle out.