The aim of this essay is two: at first I will illustrate the early life and achievement of the ‘forgotten' Irish Catholic painter, James Barry (1741-1806), who was from Cork, a southern capital town of Ireland and subsequently became a professor of painting at the Royal Academy in London (but expelled in the end). Secondly I will also show the close relationship of the painter with his country-fellow aesthetician and political philosopher, Edmund Burke (1729-97) by examining two Burke' s portraits by Barry both at Trinity College, Dublin (executed in c. 1771) and at National Gallery of Ireland (executed in c. 1774) with referring to their correspondence. Eventually I conclude that the Cork connection, in particular the Burke connection was very strong and important for Barry' s progress as a unique ‘established' artist in the late 18th century London, though Barry' s views of Art had been little by little developed in a different way from Burke' s ones since the painter' s 7-year-journey in the Continent, which in reality Burke and his family had financed. We can see a kind of ambivalent feeling, or the mixture between friendship and animosity of Barry toward his best country patron in these two oil paintings in Dublin.