I got a BA in English before I got my MA in psychology, and I’ve always been fascinated by language. I learned that languages are – other than dead languages like Latin – living things that evolve over time, to capture meaning and convey information. So, my first point is that “hip,” “cool,” and “woke” are just words, with meanings that vary from person to person. What’s cool to you might not be cool to me. But in my experience, many people use hip and cool interchangeably, and apply the term hip to places like coffee shops and to things that can be bought, like clothes or haircuts. This is a significant departure from the original meaning, in which hip is a state of mind.
Cool is in the eye of the beholder, and it applies to people, places, things and actions: you can eat at a cool tavern, with cool friends, wearing cool clothes, and listening to cool jazz. Cool fads come and go, and the cachet of cool is used to move a lot of merchandise. Things can be made to seem cool by marketers and influencers. Certain things cannot be cool, like prisons.
Hip can’t be bought or rented or worn or inhabited, although marketers have used the word as an adjective, to be applied to this destination or that product. In its original meaning, hip can only be applied to persons. Dialectically speaking, you either are or are not hip – but it can also be seen as existing along a continuum. A synonym for hip is “aware,” as in “hip to what’s goin’ down.” “I’m hip” doesn’t mean the same thing as “I’m cool”; it means “I understand.” To be hip is to be in the know, to see what un-hip people don’t see. Hip originated in Black dialect, because people of color tend to be aware of things that the majority of white people are blind to – as I once was. If you were hip, you kept your eye on what The Man was up to.
I wasn’t truly hip to American racism until, as an Army lieutenant, I attended the Defense Race Relations Institute (DRRI), to be trained as a race relations education officer. Sure, I had been aware of some aspects of racism before then. I knew that people of color were frequently discriminated against. Although I ‘d had Black classmates and teachers at the international school I’d attended in Vienna, my Georgia high school didn’t integrate racially until my Junior year. I hated racism and thought I was pretty well-informed about it.
But it wasn’t until my immersion in race relations education at the DRRI that I truly became “hip to what’s goin’ down” in America. Not only did I learn from classroom instruction, but in late night discussions in the barracks with brown- and black-skinned classmates (as well as a few Asians and Native Americans), who talked frankly about their own life experiences. We were the pilot class at the DRRI, and we felt a sense of brotherhood and trust. I became hip to the reality that white people live in a different America than people of color. I began to see things that I had been blind to.
Just as religious people can be guilty of “holier-than-thou” attitudes, it’s possible to fall into “hipper-than-thou” judgments. Hipness is perhaps best viewed as existing along a continuum, and where you place yourself on the Hipness Scale may not be where other hip people would place you. But it’s not a contest.
The concept of hipness seeped into white consciousness via the so-called Beat Generation, especially through the writings of Jack Kerouac. (He wrote that his definition of hip was someone who could score drugs in a foreign country.) The Beat Generation had a great influence on the Baby Boomer generation, and hipness was so central to the youth rebellion of the sixties that the long-haired, tie-dyed cultural rebels became known in the media as hippies. Not all of them liked the term, but the so-called hippies prided themselves in “knowin’ what’s goin’ down” and “dropping out” of conventional society. They kept their eyes on what The Man was up to.
Playwright Lorraine Hansberry wrote, “There are no “squares” . . . Everyone is his own hipster.” What she meant by hipster was something entirely different from the contemporary meaning of the word, as I understand it. These days hipster seems to describe a style or a lifestyle and, to me, more resembles “cool” than the original meaning of hip. Perhaps the word “woke” is the contemporary analog of “hip to what’s goin’ down,” with a side of political correctness.