What does Matthew 11:17 mean?

Jesus has compared the generation of Israelites in His day to children sitting in the marketplace wanting to play games with each other. He describes them as calling to their playmates and complaining that the others did not dance when they played the flute or mourn when they sang a dirge. Those specific games might seem odd to modern readers. Apparently, though, it was common in this era for children to play "wedding" and "funeral," acting out the activities of those events.

While playing "wedding," a child might pretend to play the flute while others danced as if at a feast. If they were creating a "funeral," someone would perform a sad song while the others "mourned." Mourning then went far beyond silent grieving to loud wailing and "beating the breast," which is what the word for "mourn" means.

How is this like the generation of that day? Jesus shows in the following verses that the people of the time, maybe especially those in power, complained about both John the Baptist and Jesus for not "playing" as a prophet and a Messiah should, according to popular expectations. Those expectations, of course, are wildly inconsistent. The point is that no matter what they see, some people will demand the opposite, simply out of hard-headed resistance to God.