This passage has many similarities to Matthew's Sermon on the Mount.  Luke says that the scene was a 'level place' (Luke 6:17) so some have called it the 'Sermon on the Plain' – although it may well have been a level place on the same mountain.  Jesus is specifically teaching His apprentice apostles, but an eager crowd also gathered to hear what He had to say (Luke 7:1; Matthew 7:28-29).  Ministry would be very hard for the Twelve.  With their Master, they would have to experience hunger and sorrow.  As leaders of the Early Church, many would be persecuted to death, while others suffered al

Woe is a slightly old-fashioned English word.  It means, 'grief is coming' which is a fair translation of the Greek word used here.  It is both a prediction and a warning.  This 'woe' is the other side of the coin to the 'blessings' in verse 20.  There, the poor who seek God's kingdom are satisfied.  Here, the rich seem to be self-satisfied; they have already reached the climax of contentment and there is nothing more for them.  Like the rich fool (Luke 12:15-21), everybody leaves everything when they die: the more they have, the more they leave.  

Popularity opens the door to many temptations, especially for religious people.  The admiring crowd with their personal compliments are powerful tools to reopen the old life of sin.  Corrupt human nature longs to be the centre of attention, with the ability to influence, persuade, command or simply bathe in the glory of human approval.  Whenever we take glory without passing it on to Christ, we put ourselves in His place – that is the danger-zone where Satan can tempt us that we are above our Maker, and therefore we can do whatever we like.

This verse has become a part of colloquial English, although most people do not know where the phrase comes from.  It is the fifth of Jesus' seven sayings in Luke 6:27-31 about the unconditional love which should characterise all the citizens of God's Kingdom: love your enemies (v27); do good to those who hate you (v27); bless those who curse you (v28); pray for those who ill-treat you (v28); do not fight back (v29); give without demands (v29-30); treat others as you would like to be treated (v31).