Key West

St. James Encyclopedia of Pop Culture by Paul Ashdown

Located on an eight-square-mile coral island off the southern tip of Florida, Key West is the southernmost city in the continental United States. Its location and environment give the place a mystique as the Last Resort, the place where mainland North America dribbles to an ambiguous end in the Caribbean. As an artifact of popular culture, Key West generates powerful and often contradictory cultural messages: it is at once a quintessential Navy town and a haven for literary figures, beachcombers, and assorted eccentrics. During the Cuban Missile Crisis in 1962 and thereafter, it served the rhetoric of American presidents as a rugged outpost of democracy vis-à-vis Castro's Cuba with its Russian missiles "just 90 miles from our shores."

Contrary to popular belief, the name Key West has nothing to do with the island's western aspect in the Florida Keys, which seem to drift languorously from the mainland like a strand of seaweed. The name is really a corruption of Cayo Hueso (Island of Bones), the name given the island by Spanish explorers after they reputedly found the skeletal remains of native people slaughtered in a fierce battle. Perhaps the coral rock that forms the island suggested bony encrustations to superstitious sailors wary of shipwreck on the jagged reefs that have long made Key West a nautical graveyard and a refuge for smugglers, salvagers, and castaways.

For much of its history, Key West has been the site of a U.S. Navy base. Commander David Porter established the first Navy presence there in the 1820s, and imagined he had created the "Gibraltar of the Gulf." Key West prospered as the only southern city to remain under Union control throughout the Civil War. At the time of the Spanish-American War, the entire Atlantic fleet was based in Key West's harbor. During World War II, the island was known rather dubiously as the "Singapore of the West." Resident poet Elizabeth Bishop predicted in 1942 that after the war a ruined Key West would be "nothing but a naval base and a bunch of bars and cheap apartments." The island regained some of its dignity in 1946 when President Harry Truman procured the Naval commandant's headquarters for his "Little White House." Although its presence was much diminished by the 1990s, the Navy still owned a quarter of the town at century's end.

All things nautical contribute to the island's famous ambiance. Winslow Homer discovered Key West in 1885, finding watercolor the perfect medium through which to capture the shimmering cerulean seas and lush green landscapes drowsing under a tropical sun. For poet Wallace Stevens, the essence of Key West was its aqueous ambiguity, its ephemeral substance surrounded by the "ever-hooded, tragic gestured sea." His well-known poem, "The Idea of Order at Key West," can be interpreted as a hymn either to order or disorder, or to a subjective reality simultaneously negotiating between both. Even the act of withdrawing to the bustling, commercial North, and away from sultry Key West, can bring uncertainty, as Stevens laments in the poem "Farewell to Florida." Here, the poet watches from a ship as "Key West sank downward under massive clouds/And silvers and greens spread over the sea. The moon/Is at the mast-head and the past is dead. But yet: Her mind had bound me round."

More than any other writer, Ernest Hemingway is associated with Key West in the popular mind. After leaving Paris in 1928, Hemingway acted on the suggestion of fellow writer John Dos Passos and established residence in a rented house in Key West with his wife, Pauline. In 1931, the Hemingways bought an 80-year-old limestone villa where they lived together until they divorced in 1940, and which now serves as one of the island's principal tourist attractions. Hemingway wrote several short stories, many articles, and one novel, To Have and Have Not, about Key West, which he portrayed as seedy, decadent, and impoverished, "the St. Tropez of the poor." Hemingway's growing celebrity soon obscured the more prosaic details of his life. Leicester Hemingway writes that his brother's Key West period "begins in the public mind with a picture of a bronzed giant fighting huge fish, then heading inshore for the roughest, toughest bar to celebrate the catch, possibly pausing somewhere to beat out a letter to Esquire, using words growled from one corner of the mouth. It was not like that ever." But the Hemingway Days Festival, which began in 1981, celebrates the machismo image of the writer with parodies and pastiches of his works, contests in which white-bearded and barrel-chested men compete in Hemingway lookalike contests, costume parties, arm-wrestling competitions, and drinking bouts at Sloppy Joe's Bar.

A long line of other writers, including Jack London, Tennessee Williams, Robert Frost, John Hersey, Tom McGuane, Truman Capote, Alison Laurie, Elizabeth Bishop, and Annie Dillard, have found Key West congenial. Popular crime and mystery writers such as Laurence Shames and James W. Hall have used the city as the backdrop for their stories, exaggerating its eccentricities. In "Bones of Coral," Hall describes Key West as an "outpost for the unstable, maladjusted, the just plain insane. If they weren't insane when they came, they turned that way. They became islanders, devolved creatures."