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Although often characterized as an apolitical artist, Andy Warhol began making portraits of political figures early in his career. By the end of his life, Warhol had visited the White House on at least five occasions, at the request of three different presidents. In examining his portraits of presidents and his interactions with First Families from the Kennedy administration to the Reagan administration, we can see both Warhol’s growing willingness to delve into the realm of politics and Warhol’s increasing acceptance by the political elite.

Warhol’s first-known rendering of JFK appears as a rough sketch in one of his early drawings of a newspaper front page, Pirates Sieze Ship (1961). In his book Popism (1980), Warhol remarked, “I’d been thrilled having Kennedy as president; he was handsome, young, smart…” yet in this drawing Kennedy appears sweaty and tired after a “tough day” of cabinet meetings shortly after his inauguration.1  The attractive and dynamic Kennedy that we tend to remember shows up in Warhol’s artworks from later in the decade. Kennedy’s smiling face is partially visible in some of Warhol’s Jackie portraits, in which Warhol had appropriated a photograph of the happy couple greeting their supporters in Dallas.