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The cave painters at Lascaux may have been the last to get along without patrons, and for all we know, they had others bringing home their bison. When the artist’s patron becomes his subject, the situation grows even more dicey. Uneasy is the hand that holds the brush that paints the slaver’s noble countenance, the merchant’s proud wife, the robber baron’s weakchinned heir.

In 1992 the Newport Art Museum assembled an exhibition of about two hundred portraits spanning a period of three centuries. Taken together, the paintings represented not only a who’s who of Newport but a retrospective of American portraiture from colonial times to the present, from Gilbert Stuart and Robert Feke to—and here’s the surprise—Diego Rivera and Richard Lindner. Many of the portraits, which belong to the sitters or their descendants, have since returned to their owners, but now the museum has put together 196 of them in a volume called Newportraits , published by the University Press of New England.

The collection, like the history of the city, has its high points and low. Settled in 1639 by a group fleeing the religious persecution of the Massachusetts Colony, colonial Newport was both celebrated and condemned for its tolerance. While Cotton Mather fulminated against this “common receptacle of the convicts of Jerusalem and the outcasts of the land,” merchants grew rich from the Triangular Trade, twenty-two distilleries turned molasses into rum, and one of the first paintings in the collection, a circa-1740 portrait of Mary Winthrop Wanton by Robert Feke, featured a décolletage so daring that in 1859 the directors of the local Redwood Library commissioned Jane Stuart, the daughter of Gilbert, to paint, under protest, a nosegay over the cleavage. Jane Stuart called the retouching an act of vandalism, but the patrons’ prudishness trumped the artist’s eye. And she had a widowed mother and several sisters to support.

Occupied by the British during the Revolution, Newport never recovered its former prosperity, despite its popularity as a summering spot for Southern gentry fleeing their native heat and malaria in the first half of the nineteenth century and New England intellectuals seeking one another’s company in the second. Two Pulitzer Prize-winning writers, Maud Howe Elliott (awarded the prize with her sisters Florence Marion Howe Hall and Laura E. Richards for a biography of their mother, Julia Ward Howe) and Edith Wharton, make appearances in this collection. Despite Wharton’s comment that she “did not care for watering-place mundanities,” she followed the trend toward fashionable European painters and sat for the Englishman Edward Harrison May.

By then the Gilded Age had arrived. The village built on tolerance had become the resort notorious for exclusivity. “Newport was the very Holy of Holies, the playground of the great ones of the earth from which all intruders were ruthlessly excluded by a set of cast-iron rules,” wrote Elizabeth Drexel Lehr, whose husband, Harry, succeeded Ward McAllister as the arbiter of social acceptability.

Sitting for a portrait is an act of hubris. The subject is saying, “I am worth looking at.” It is also a statement of trust in the artist: “I will let you fashion the face I show to posterity.” Even after photography had introduced a less risky road to immortality, the rich, the powerful, the celebrated—and those who wanted to be—continued to take the gamble.