Jesus is at His subversive best in that part of Matthew's Gospel usually called The Sermon on the Mount. In a series of clipped images, Jesus portrays not how to be happy, but what happy people look like.
Below are links to a series of messages I presented on Jesus' sermon. The series is called The Happiness Project. In a few days, I'll pick this series back up again with thoughts on the balance of Matthew, chapter 5, which is really something of an explication of the points that Jesus makes in the first twelve verses.
The Poverty That Leaves You Rich
The People Who Make a Difference
The Diet That Will Make You Happy
What Mercy Does
The People Who See God
The People Who Make Peace
Happy When the World Turns Away