In my humble opinion, this reading is often misunderstood. I’ve heard it used to beat down people who have enough money to live, who experience joy in their work or play, who do not appear to suffer. I’ve heard it used to exalt suffering, suggesting that suffering is the hallmark of a faithful follower. I think this interpretation is off.
Jesus was speaking to people who were suffering already. Jesus’ words were intended to bring hope to a hopeless people. His words to those in power condemned their behaviors – not because they had money, food, or laughter, but because they had those things at the expense of others, and at the exclusion of God. When we use our money, food, and joy to lift up others, Jesus rejoices with us all.
He came down with them and stood on a level place, with a great crowd of his disciples and a great multitude of people from all Judea, Jerusalem, and the coast of Tyre and Sidon. They had come to hear him and to be healed of their diseases; and those who were troubled with unclean spirits were cured. And all in the crowd were trying to touch him, for power came out from him and healed all of them.
Then he looked up at his disciples and said: “Blessed are you who are poor, for yours is the kingdom of God. “Blessed are you who are hungry now, for you will be filled. “Blessed are you who weep now, for you will laugh. “Blessed are you when people hate you, and when they exclude you, revile you, and defame you on account of the Son of Man. Rejoice in that day and leap for joy, for surely your reward is great in heaven; for that is what their ancestors did to the prophets. “But woe to you who are rich, for you have received your consolation. “Woe to you who are full now, for you will be hungry. “Woe to you who are laughing now, for you will mourn and weep. “Woe to you when all speak well of you, for that is what their ancestors did to the false prophets.