Unless your righteousness surpasses that of the Pharisees...More often than not we read sarcasm in these words of Jesus. Did he really imply that the Pharisees are righteous? Aren’t the Gospel accounts awash with criticisms which Jesus directed towards the Pharisees and other religious leaders? Doesn't Jesus himself warn us to be weary of the yeast of the Pharisees, that is, of their hypocrisy? What could Jesus have intended by his statement?
If we put aside the bias through which we have come to look at the Pharisees, we will realize that the cause of conflict between them and Jesus wasn’t the lack of righteousness on their part but rather their failure to live up to the billing of the offices that they occupied. As those to whom God had thrust the responsibility of shepherding God’s people, the religious leaders were expected to lead by example. Simply put, Jesus was always reminding the religious leaders that to whom much is given, much is expected. The religious leaders were indeed given much (status, leadership, honor) but they forgot that much was expected from them as well (responsibility, role modelling).
Jesus was not being cynical when he referred to the righteousness of the Pharisees (a righteous person is one who has "righted" the self before God). In literal sense, the Pharisees were a righteous bunch: they kept away from all that could make them sinners before God. They kept the law. They upheld the tradition. They took care of the vertical relationship (between God and man). Jesus recognized that much. That which was lacking in them, and which Jesus wished his hearers to have, is the taking care of the horizontal relationship (between man and man). For Jesus, it made little sense to be right with God if one couldn't be right with one's fellows. For being right with one's fellows is the practical application of being right with God. To the most part, keeping right with God (such as observing the law) is a downright passive affair. The Pharisees excelled in this area. They tended to avoid keeping right with their brothers and sisters since it is active and demanding. Of course, one can do with only taking care of the vertical relationship. But a follower of Jesus must, and this is a command of Jesus, ensure the horizontal accompanies the vertical one. One who does this surely surpasses the righteousness of the Pharisees. Jesus did this, and it becomes a prerequisite for being a disciple of Jesus.