Basketball.
There are 68 teams in the U.S. College Basketball Tournament. The bottom eight play an extra round; the winners get the bottom seeds in the main tournament. The main bracket has 64 teams in a single elimination tournament.
In the main bracket, how many games will be played, total?
If you just flipped a coin, what is the probability that you'd win them all?
Warren Buffet has offered $1 Billion Dollars to anyone who does pick all the games. What are the chances he will lose 1/60th of his money?