Simeon entered the gate of Emesa (after spending many years in desert) dragging a dead dog. Schoolchildren saw him and shouted (κράζειν) "Hey, a crazy abba...". The next day, a Sunday, he entered the church, extinguished the lights and threw nuts at women. On the way out of the church, Simeon overturned (έστρεψεν) the tables of the pastry chefs (πλακουντάριοι). Such playing the fool was subject to insults, abuse and beatings, which Simeon endured with patience. In spite of his seemingly strange behaviour, Simeon the Holy Fool healed many possessed people by his prayer, fed the hungry, preached the Gospel, and helped needy citizens of the town. Many of Simeon’s saintly deeds were done secretly.
His ministry also included trying to save a man whose eyes suffered from leucoma. Jesus had previously used saliva and clay to cure a man of blindness, and when the man with eye disease approached Simeon, he anointed the man's eyes with mustard, burning him and aggravating the condition to the extent that he reportedly went blind. Later the eyes were healed by the advice of Simeon, who used such way to explain the man's sins and bring him to correction.
Symeon played all sorts of roles foolish and indecent, but language is not sufficient to paint a picture of his doings. For sometimes he pretended to have a limp, sometimes he jumped around, sometimes he dragged himself along on his buttocks, sometimes he stuck out his foot for someone running and tripped him. Other times when there was a new moon, he looked at the sky and fell down and thrashed about.
The life of Simeon the Holy Fool was described by Leontios of Neapolis, who symbolically compared his life to that of Jesus, whom the saint tried to imitate in his own way. According to Leontios:
While the saint was there (in Emesa), he cried out against many because of the Holy Spirit and reproached thieves and fornicators. Some he faulted, crying that they had not taken communion often, and others he reproached for perjury, so that through his inventiveness he nearly put an end to sinning in the whole city.
The only person in Emesa, with whom Simeon did not play a fool, was deacon of the church in Emesa, his friend John. One time Simeon saved John from execution when he was falsely convicted. Shortly before his death Simeon, by the illustration of Leontios of Neapolis told to John:
I beg you, never disregard a single soul, especially when it happens to be a monk or a beggar. For Your Charity knows that His place is among the beggars, especially among the blind, people made as pure as the sun through their patience and distress. . . . [S]how love of your neighbor through almsgiving. For this virtue, above all, will help us on (the Day of Judgment).
The saint died about 570 A.D. and was buried by the city poor in a place, where the homeless and strangers was buried. While the body of Saint Simeon were carried, several people heard a wondrous church choir.
Only after his death the secret of his imitative foolishness came to light. Some inhabitants remembered his acts of kindness and reportedly strange and powerful miracles.
The feast day of Saint Simeon is marked by Christians on July 1 and on July 21 in the Byzantine calendar .