heyitsnorton:

Hipster (modern) comes from hipster (fifties), coming from hip, coming from hep. Hep was first used in print in 1908, and meant somebody who was aware, or savvy. Nobody really knows where “hep” comes from. But there are lots of apocryphal stories that are fun! My favorite:

According to David Maurer in The American Confidence Man, it came from a misunderstanding of the original usage, which came from the name of an 1890’s Chicago saloon owner, Joe Hep. His place was a grifter hangout, but he didn’t know it. Evidently, he thought all his customers were just businessmen and salesmen. The story goes that when a musician or other stranger was brought over to a con man table, the question “Who’s your friend?” was answered, “Oh, he’s Joe Hep.” This meant the guy didn’t have a clue and it was all right to talk around him using grifter’s slang. The “friend” usually misunderstood, and taking it as a compliment, thought that “Hep” meant “with it” or “cool,” and that is how the term gravitated into the musician’s lingo.