Born in Mytilene, Theophilos showed an inclination towards painting at a very young age, while having learned the basics from his grandfather. In 1883, he left Mytilene island and settled in Smyrna where he created the first period of his work. Afterwards, he moved to Pelion, Volos, where he was decorating shops, cafes and inns for 30 years, living in poverty and ridiculed by the residents of the region because of his eccentric appearance. In 1927, he returned to Mytilene where he continued to work on the third period of his paintings until his death. He met the renowned art critic Stratis Eleftheriadis (Tériade) to whom Theophilos owes the recognition of his work as well as its international publicity. In 1961 the Louvre presented a retrospective exhibition of his works, while in 1965, the Museum of Theophilos was inaugurated in his birthplace.
The typical Greek characters and his continued effort towards a faithful illustration of Greek folklife and history characterize his work. Through the naivety, modesty and freshness of his paintings he expressed the love for his country in a remarkable way.