“The origin of hip (and its partner, hep; the words are related) is, unsatisfyingly, unknown. The term first appeared at the turn of the 20th century, and quickly became widespread. Its meaning at this early point was “aware; in the know,” and it was not widely used by African-Americans. It wasn’t until the late 1930s and early 1940s, during the jive era, that the modern senses—”sophisticated; currently fashionable; fully up-to-date”—arose.”