Warhol was born Andrew Warhola (he later dropped the a to seem less ethnic) in 1928, to an impoverished working-class family. His parents had immigrated to the United States from Mikova, in what is now Slovakia. His father was a coal miner; Warhol’s first place of residence was a tar-paper shack, his second an apartment without a proper toilet. Thanks to the postal bonds set aside for him by his father (who died when Andrew was 13), Warhol was the first person in his family to attend college.

At Carnegie Tech, he was a moonbeam: pale, fanciful, elfish, and already remote. And talented. Living Room, which he painted as an undergraduate in 1948, is doubly remarkable: The tiny watercolor is autobiographical, a depiction of his childhood home, and in being so expressive of the intimacies of poverty, it looks more like one of Vincent van Gogh’s evocations of peasant life than like a Warhol. It is a work of supreme tenderness, with its subject matter’s dinginess balanced against the sublimity and grace of the everyday.

After graduating in 1949, Warhol moved to New York City, and quickly became known as, in one graphic designer’s words, “the best shoe drawer in New York City.” He was hired by the I. Miller company to produce images for its weekly footwear ads in The New York Times. He did illustrations for the slickest magazines and piecework for the biggest corporate accounts, made Christmas cards for Tiffany and perfume ads for Bonwit Teller. He borrowed a technique from the Lithuanian-born American painter Ben Shahn of tracing a sketch in ink, then pressing the wet ink against a piece of absorbent blotting paper to transfer the image. It made for a sensitive line, a line with perceptible temperament, but by a process of reproduction that troubled any idea of an “original” version touched by the artist’s hand.

By the end of the 1950s, he was famous as a commercial artist, and his “cockroach period,” as he put it—his years of living with insects and roommates—came to an end. He bought a four-story townhouse on Lexington Avenue, off 89th Street. But he wanted to be a fine artist, and in the 1950s, Warhol still associated being a fine artist with being an expressive one; and to work expressively was to all but admit he was gay. “If you look at the Boy drawings, for instance, they’re all about touch,” noted Neil Printz, referring to a series of erotic pieces Warhol made in the mid- to late ’50s. “There’s this contour line that almost seems never broken, as if he never lifted his eyes from the subject, and his hand kept moving constantly over the contours of a young man’s body.” His first gallery exhibition, in 1952, was titled “Fifteen Drawings Based on the Writings of Truman Capote,” and included work that was too fey for the times.

The epochal turning point came in 1960, when Warhol showed a handful of acquaintances and art-world players two paintings of a Coke bottle. One was a lyrical meditation in an abstract-expressionist mode, complete with Jackson Pollock–style drippings. The other was as clean and cold and devoid of personal expression as the item itself. “It’s naked, it’s who we are,” said one viewer, and Warhol, in step with changing tastes, began working in the Pop mode. But at the end of 1961, his new work had not been shown in a gallery, and was felt to be derivative of Roy Lichtenstein’s and James Rosenquist’s.