Van Sant has lived in Hollywood on and off for around 45 years, since he graduated from the Rhode Island School of Design (RISD). His paintings offer a composite of his memories of and experiences in the area, which he renders with dreamy, mythic haziness. The architecture outside Van Sant’s window, near Hollywood Boulevard, populates his canvases. The Capitol Records building, round with a white spike protruding from its tip, becomes a pastel layer cake of a structure in Untitled (Hollywood 4) (2018–9). The Griffith Observatory caps the top of a hill in Untitled (Hollywood 16) (2018–9). Rendered simply, with straight white columns and a sky blue dome, the building resembles some kind of holy temple that the crouching figure at the bottom of the painting is trying to reach.
Two poles of the Hollywood ecosystem—the Oscar statuette and the homeless population—inspired Van Sant’s figures. “I just realized these are very uniform-looking, golden figures,” the artist said about his solitary men. “I thought, ‘oh, that kind of looks like the Oscars.’ The Oscar is so pervasive as a desired object within the town.” Hollywood Boulevard plays host to both the Kodak Theatre (known as the Dolby Theatre since 2012), which hosts the awards each year, and panhandlers. He has long reacted to the drifter youth in his neighborhood: They inspired My Own Private Idaho and its charming, degenerate characters made indelible by River Phoenix and Keanu Reeves (though in the film, Van Sant transports them to Portland).