Q: Does anyone know (and can provide citations) for when this usage of hipster started?
According to the OED, the earliest use of hipster in print is its 1941 definition in Jack Smiley's Hash House Lingo:
Hipster, a know-it-all.
And according to Wikipedia:
Hipster, as used in the 1940s, referred to aficionados of jazz, in particular bebop, which became popular in the early 1940s. The hipster adopted the lifestyle of the jazz musician, including some or all of the following: dress, slang, use of cannabis and other drugs, relaxed attitude, sarcastic humor, self-imposed poverty and relaxed sexual codes.
According to a 2009 Time article, the current meaning emerged in the 1990s:
The word would fade for years until it was reborn in the early '90s, used again to describe a generation of middle-class youths interested in an alternative art and music scene. But instead of creating a culture of their own, hipsters proved content to borrow from trends long past. Take your grandmother's sweater and Bob Dylan's Wayfarers, add jean shorts, Converse All-Stars and a can of Pabst and bam — hipster.
Wikipedia cites a 2003 satirical definition:
In 2003, Robert Lanham's satirical book The Hipster Handbook described hipsters as young people with "mop-top haircuts, swinging retro pocketbooks, talking on cell phones, smoking European cigarettes... strutting in platform shoes with a biography of Che Guevara sticking out of their bags." Lanham further describes hipsters thus: "You graduated from a liberal arts school whose football team hasn't won a game since the Reagan administration" and "you have one Republican friend who you always describe as being your 'one Republican friend.'"
A quick dip into Usenet gives the following quotes.
So far, Bob's popularity has been limited to hipster counterculture circles.
And what a thriving metropolis it is! Why, I can hardly walk across my
hall, much less the campus, without running into so much musical and
other diversity that it makes me want to puke! I only wish I could be
so kool [tm] as all these hipster dudes and dudettes walking around this
But there's this one dude on campus......he must be like the most totally
awesome hipster goth-monster type dude! Why, he even mentions some band
called SoM! I don't know what it stands for or what they sound like, but
they must be like so totally freakin' awesome cuz he listens to 'em! I
think they're industrial though, cuz that's what he said. And I want to
be just like him when I grow up from just wearing black to wearing dark
black. I heard someone told him that SoM wasn't really industrial! gasp!
But he shut their mouth when he deftly replied that they were nanny-
nanny-boo-boos and they didn't really know what industrial was and
were just closed-minded potty-mouths who didn't listen to real music.
Boy, I wish I could be just like him! sigh
Yes, I can see how it [Totoro] looks boring at first sight. IMHO, the marketing of
the recent US release botched this, presenting it as a G-rated kiddie movie
that turns out to be too sweet for the taste of most real American kiddies,
instead of going after the ironic hipster crowd or adults nostalgic for
If it has "lost its hip appeal" to you,
then I suggest you are a "hipster" who is not in search of a plain old
good time, but is looking for this year's new fad. In that case, I
think you SHOULD leave rave behind, to those of us who still care about
it, and go find something "trendy" and "cutting-edge" to do...