From left to right, gallery owner Leo Castelli, Pop art dealer Ivan Karp and artist Andy Warhol, all at Castelli's gallery in 1966. An early supporter of the artist, Castelli would be the subject of a silkscreen Warhol portrait wearing a business-like suit and tie.  Credit: Sam Falk/The New York Times/Redux.

21 Days of Andy Warhol is Sotheby’s three-week celebration of the essential 20th century artist with one-a-day stories and videos about Warhol’s origins, influences, inspirations, all leading up to the sale of important Warhol pieces in our Contemporary Art Evening auction 13 November.

NEW YORK - Andy Warhol moved from Pittsburgh to New York City a week after graduating from the Carnegie Institute of Technology, in June 1949. He initially roomed with friend and college classmate Philip Pearlstein, the realist painter. It wasn't long before Warhol's skills as a commercial artist were noticed by art directors. By the early 1950s, he was well on his way to becoming one of the city's most well-known fashion illustrators. Warhol hit upon a winning technique, combining tracing and ink-blotting, which gave his work a fresh look that art critic David Hickey would later call "exactly wrong." A turning point in his career came in April 1955, when the shoe company I. Miller & Sons brought on Warhol as a fashion artist.

Meanwhile, some of Warhol's earliest attempts to court New York's fine art establishment were being met with rebuffs. Through Pearlstein and another artist-friend, Joseph Groell, both members of the Tanager gallery collective, Warhol twice unsuccessfully submitted for exhibition selections of his so-called "boy drawings," according to the Warhol biography Genius of Pop. Pearlstein suspected the drawings' homoerotic subject matter (among the evidence of Warhol's participation in New York's veiled gay sub-culture of the '50s) led to their rejection, Pearlstein recalled to the biographers, by "the macho painters at the Tanager" – namely Abstract Expressionists.

A model wears a John Frederics straw hat with a Lady Manhattan Robaix silk broadcloth shirt and Dior make-up, with an Andy Warhol rabbit drawing on the wall behind her, circa April 1, 1955. Photograph by Frances McLaughlin-Gill. © Condé Nast Archive/Corbis.

Smaller galleries did accept Warhol's work, however, and between 1952 and '59 he had seven shows. He even had a drawing included in a 1956 Museum of Modern Art group exhibition (Warhol sought to have the work added to MoMA's permanent collection, but he was turned down). By the time Robert Rauschenberg and Jasper Johns were gaining acclaim – for artwork that dismissed many of the underpinnings of then-prevalent Abstract Expressionism – Warhol was poised for ascent.

In early 1961 Warhol completed a flourish of paintings, with imagery lifted from newspaper ads and comics that anticipated the detached, hard-edged style of his pivotal early-'60s work, but also appeared beholden to AbEx drippiness. Five of the works were shown in a window display at the Bonwit Teller department store. That same year he bought a Johns drawing, Light Bulb, from Leo Castelli's gallery, adding to his increasingly impressive art collection. Johns was an idol of Warhol's, and he saw the Castelli Gallery as the pinnacle of the New York art world. In November, following a session of subject-matter conceptualizing with Muriel Latow, a gallery owner in the artist's circle, Warhol executed the first of his iconic paintings of Campbell's soup cans. Irving Blum, of the groundbreaking Ferus gallery, in Los Angeles, saw them at Warhol's home studio in December and offered to show them.

Jasper Johns and Andy Warhol at the opening of The Art Museum of South Texas, circa October 6, 1972. © Condé Nast Archive/Corbis.

At this time Warhol was also aggressively cultivating his network of art-world contacts, which included Ivan Karp, of the Castelli Gallery, and Henry Geldzahler, an ambitious young curator at the Metropolitan Museum of Art. And although his work hadn't yet been exhibited by a major gallery, Warhol was featured in a May Time magazine story heralding what would be known as the Pop Art movement. On July 9, Warhol's first solo exhibition opened at Ferus; each of the 32 canvases on view depicted a different Campbell's soup flavor. Despite their tepid reception, Blum decided to purchase them all for himself, reconceiving the paintings as a single artwork.

Over the next few years Warhol's work was shown with increasing regularity. His first solo show in New York took place in November 1962 at Eleanor Ward's Stable Gallery and included his earliest depictions of Marilyn Monroe, who had died on August 5. (The show sold out. Architect Philip Johnson purchased Gold Marilyn and gave it to MoMA.) Illeana Sonnabend, the Paris gallerist and Castelli's ex-wife, exhibited Warhol's work in her 1963 group show, "Pop Art Américain." Sonnabend would hold Warhol's first solo show in Europe early the following year.

Andy Warhol's Thirteen Most Wanted Men hanging at  the Philip Johnson-designed New York State Pavilion at the World's Fair in Flushing Meadow, Queens. © Bettmann/CORBIS.

In 1964 Warhol stirred up controversy with his contribution to the Johnson-designed New York State Pavilion of the World's Fair, set in Queens' Flushing Meadow. Thirteen Most Wanted Men, based on NYPD mug shots, was unveiled, almost immediately decried, painted over, and ultimately covered with black cloth for the remainder of the fair. But if the episode signaled a failure, it was soon succeeded by a triumph. In May, Warhol parted ways with Ward; with Karp's help, he had signed on with Castelli Gallery. Once hesitant about the budding artist, Leo Castelli mounted his first Warhol show in November. The subject: Warhol's seminal Flowers series. 

Tomorrow: Andy Warhol and the Factory