From when God stops making sense (or, my favorite part of the Old Testament):

But for Psalms and wisdom literature, life isn’t black and white. Life is messy, unpredictable, and often makes no sense.

These books take issue with the storyline and its moral. They interrogate the black and white script and conclude, “Life isn’t that straightforward.”

Job loses everything he has except his life. The script (e.g., Deuteronomy) says that such calamities are by God’s hand, a response to disobedience. Yet we learn from Job that this is not the case.
Ecclesiastes questions the “world order” God has made: nothing we do matters, since we all die and are driven to the point of madness at the thought of our futile existence.
A number of psalms lament God’s absence in the world. Like Psalm 73–where the author can’t get his head around how a just God can allow the wicked to prosper.
Or Psalm 89–where God is in effect called a liar for promising that one of King David’s descendants would always be on the throne in Jerusalem and then allowing the Babylonians to kill off the last of David’s royal line and take the people captive.