The Renaissance ended with a bang and Rome was ransacked and devastated by imperial troops. Philip would walk the streets seeking opportunities to engage people in conversation and offer them help. He'd stop people on the streets asking, "when shall we begin doing good?" and people would want to actually do good. Hospitals were founded and staffed - people joking and singing amongst the rooms and halls.
What he's most noted for is founding a society called 'the Congregation of the Oratory'. Evenings would find his band of disciples gathering to talk and pray and listen to scripture readings and music in a room they called their oratory. Originally the Oratory suffered through a period of "heretic" accusations since laypersons preached and the hymns sung were vernacular - of the ordinary dialect.
The Church itself was needing conversion and Philip's humble and gay personality converted many to personal holiness. Many, including 'important' people, sought his advice, and he was a spiritual director for many. Philip wanted people to become not less, but more human through their faith in God. His mission was the streets of Rome.
There was nothing gloomy about the sanctity he preached and practiced. Philip loved jokes and laughter; he would sometimes appear in public, perfectly deadpan, wearing his clothes inside out, or sniffing a bouquet of whisk brooms. He considered a cheerful temperament to be more Christian than a melancholy one.
"A cheerful heart is more easily made perfect than a downcast one." Philip Neri's autopsy revealed an extraordinarily large heart.
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