I have to admit, I always wondered what this part of Psalm 23 meant. I thought “He anoints my head with oil” was figurative language for God keeping the Psalmist healthy. I never knew this parallel.
Anoint my head with oil
“Sheep can get their head caught in briers and die trying to get untangled. There are horrid little flies that like to torment sheep by laying eggs in their nostrils which turn into worms and drive the sheep to beat their head against a rock, sometimes to death. Their ears and eyes are also susceptible to tormenting insects. So the shepherd anoints their whole head with oil. Then there is peace. That oil forms a barrier of protection against the evil that tries to destroy the sheep. Do you have times of mental torment? Do the worrisome thoughts invade your mind over and over? Do you beat your head against a wall trying to stop them? Have you ever asked God to anoint your head with oil? He has an endless supply! His oil protects and makes it possible for you to fix your heart, mind, and eyes on Him today and always! There is peace in the valley! May our good good Father anoint your head with oil today so that your cup overflows with blessings! God is good and He is faithful!!”