His work might be seen as a bridge, at least in the tradition of figurative painting, between the old and the modern masters. Bailey paints somewhere between Piero, Balthus, Morandi, his formidable contemporaries Philip Pearlstein and Alex Katz, and painters of a younger generation like John Currin and Lisa Yuskavage, both of whom must have come under his guidance at Yale University, where Bailey has taught all of his academic career.