Anxious Girl was first acquired by Horace and Holly Solomon, important collectors and early champions of Pop Art. Active figures in New York's art scene in the 1960s, the couple's apartment came to be filled with canonical works by Andy Warhol, Roy Lichtenstein, James Rosenquist, and Claus Oldenburg. In 1966, Holly Solomon commissioned Andy Warhol to produce his now famous 9-paneled portrait of her and in doing so immortalized her reputation as the 'Princess of Pop.' This persona was further developed with more portraits of her by leading artists of the era, including Robert Mapplethorpe, Richard Artschwager, Robert Rauschenberg and Roy Lichtenstein—among them, Lichtenstein's masterpiece I...I'm Sorry, featuring a distressed young woman in tears, painted just one year after Anxious Girl. Formerly owned by Ms. Solomon, the 1965 painting now resides in the collection of The Broad in Los Angeles.