When I was growing up, Halloween was no big deal. I was taught it was All Hallow's Eve or the evening before All Saints' Day, a principle feast of the Church in the Anglican tradition. My understanding is that as missionaries came to the British Isles, they took pagan customs and reinterpreted them for the new converts. Because of the growing influence of neo-paganism and the desire for more and more kids to act out stuff that is not wholesome, I, as a pastor, have begun to downplay the trick or treat aspects and have begun observing Reformation Day as October 31st is the date of Luther's nailing his 95 thesis on the Wittenburg Church door. And the Reformation seems to be a forgotten history of Anglicanism as well in many quarters of our various denominations.
But why is Halloween so popular? My answer is that deep down we know we are the monsters we portray. In Anglicanism we believe in original sin (Article 9 of the Articles of Religion). Somewhere inside our soul lurks an ax murderer. And somewhere deep in our soul we know we are supposed to live forever hence we dress up as zombies or vampires and the like. Of course these living dead have to eat off of other living souls which means that in order to live they have to take a life. So we are conflicted human beings wanting to live forever but never able to escape our evil nature. And so when we dress up with masks and costumes, we are not really disguising ourselves inasmuch as we are revealing ourselves. It is in real life that we wear the masks.
When Jesus uses the word, 'hypocrite', He is actually saying to His audience, "You mask-wearer!" Hypocrite means in Greek 'actor'. And actors in Jesus' day wore masks to portray their characters. This is why we see the double masks, "comedy and tragedy" on theaters and playbills. Much of the Sermon on the Mount is devoted to the condition of the heart. If we hate someone we are murderers. If we lust after someone not our spouse, we are adulterers. Is it any wonder then, that when given a choice, the people asked Pilate to release Barabbas? So what if he has killed someone? He is just like one of us! Our outward appearance hides our true nature. Our outward appearance is our mask. So on Halloween, we are actually taking off our masks when we put on our costumes!
Christ came to rip our masks off and show us our nature. "You Hypocrites" is also followed by a warning of God's judgement. God's wrath will fall on all murderers, thieves and adulterers. The light of Jesus Christ shines on our dark nature. It is then we can see our need for a redeemer, someone to stand in our place and take our punishment upon Himself meeting the legal demands of the law. When we see who we truly are deep in our souls, we can with authenticity plead for God's mercy. We then die to sin and live in Him who washes us of our uncleanliness giving us eternal life, something we have always wanted deep in our souls.