In 1969, shortly after the tragic passing of screen legend Judy Garland, The Singer Sewing Company commissioned Norman Rockwell, at the height of his own fame, to create a commemorative image of Garland in her most iconic role, Dorothy Gale in The Wizard of Oz. In addition to sponsoring a television broadcast of The Wizard of Oz, for which Rockwell’s painting was published as the promotional image, The Singer Sewing Company donated the painting, along with a cottage in Judy Garland’s name, to the Motion Picture and Television Fund in 1970, where it has remained ever since.
The last decade of Rockwell's career, made famous by his covers for The Saturday Evening Post, was defined by his series of portraits of well-known Americans, including Presidents Kennedy, Nixon and Eisenhower. Rockwell was therefore a natural choice for this commission and he applied his signature wit and charm to one of Hollywood's most celebrated stars. The Wizard of Oz, which premiered in 1939, was perhaps the most whimsical film of its era and would have left an indelible mark on Rockwell. In this portrait, rather than solely capture Judy Garland as Dorothy, which he has done with a careful level of detail, he also depicts Toto, her constant companion, in her arms. The background suggests the other characters of the movie, including the Scarecrow, the Lion and the Tin Man.
The theme of Hollywood was not new to Rockwell. He first visited Los Angeles in 1930, the decade that marked a new era of the motion picture industry and the emergence of major film studios and true Hollywood starlets, including Judy Garland. Virginia M. Mecklenburg writes, "By the 1930s, movies were big business. The early era of silent films shown in storefront theaters was over, replaced by a network of studio-owned movie palaces where millions of Americans spent their entertainment dollars. Hundreds of westerns, romances, melodramas, and comedies were produced each year, with many complicated plots made possible by the 1928 introduction of 'talkies.' Handsome stars, inspiring ingènues and character actors provided fodder for movie magazines that exposed the professional stories and private lives of Hollywood notables." (Telling Stories: Norman Rockwell from the Collections of George Lucas and Steven Spielberg, Washington, D.C., 2010, p. 69) Rockwell painted several notable Hollywood themed works as a result of this trip and this culture of celebrity was of interest throughout his career.