“Cool” was in use among African Americans in Florida as early as 1935, the year in which the flamboyant African-American folklorist and author Zora Neale Hurston published her book Mules and Men. In it, Hurston tells of a marathon hoedown that welcomed her back home to Eatonville, Florida, from Columbia University in New York, where she’d been studying with the great anthropologist Franz Boas. As Hurston and her friends pile into a jalopy that will haul them from one party to another, someone asks a guy named Johnny Barton if he’s got his guitar with him. “Man, you know Ah don’t go nowhere unless Ah take my box wid me,” replied Barton, who, Hurston notes, was wearing cream-colored pants with a black stripe down the side, a starched blue shirt, and a collar pin with heart bangles on each end. “And what makes it cool, Ah don’t go nowhere, unless I play it.”

As a calling card for his Cotton Club Orchestra, bandleader Cab Calloway in 1938 published Cab Calloway’s Cat-ologue: A Hepster’s Dictionary. Described as “the first glossary ever compiled of the colorful and unique words, phrases and expressions employed by Harlem musicians and performers on Lenox Avenue,” it contained two hundred words favored by the “hep cats . . . when they talk their jive.” In Calloway’s book, “hip” means wise or sophisticated. Anyone unhip is “square” or a “Jeff.” And even in 1938, Calloway and company were already using such terms as “groovy,” “dig”—as in “I’ll plant you now, and dig you later”—and “mellow.” A “viper” was a dope-smoker, a “drape” was a suit of clothes, and a “gate” was a “cat,” as in “Greetings, gate.” He doesn’t mention the word “cool.”

Following Calloway’s Cat-ologue came a much more ambitious effort from Dan Burley, a columnist for New York City’s leading African-American weekly newspaper, The Amsterdam News. At the urging of his friend Langston Hughes, Burley in 1944 published a two thousand-word “Negro-American lexicon,” Dan Burley’s Original Handbook of Harlem Jive. Burley included street-corner conversations from the heart of Harlem’s “Stroll,” the corner of 126th Street and Seventh Avenue, between mythical hipsters Joe Q. Hipp and Sam D. Home (“Just here from Rome”); as well as jive rewrites of Hamlet’s soliloquy, “The Night Before Christmas,” and Joyce Kilmer’s “Trees” (“I think that I shall never dig/A spiel as righteous as a twig”). “Cool” isn’t in Burley’s vocabulary, either.