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Untitled (Cowboy) - Richard Prince, 1989
From the Heilbrunn Timeline of Art History:

Untitled (Cowboy)is a high point of the artist’s ongoing deconstruction of an American archetype as old as the first trailblazers and as timely as then-outgoing president Ronald Reagan. Prince’s picture is a copy (the photograph) of a copy (the advertisement) of a myth (the cowboy). Perpetually disappearing into the sunset, this lone ranger is also a convincing stand-in for the artist himself, endlessly chasing the meaning behind surfaces. Created in the fade-out of a decade devoted to materialism and illusion,Untitled (Cowboy)is, in the largest sense, a meditation on an entire culture’s continuing attraction to spectacle over lived experience.