I’m going to say that our modern sense of cool began in the 1940s with Frank Sinatra, a midnight crooner who drank in classy bars with a pack of rats. Then Miles Davis showed up and perfected the art of jazz, which was the art of improvisation, the art of making it up as you go along, and people like Kerouac started living to this beat. Teaheads began getting high together and ushered in the age of hippies – Bob Dylan turning on the Beatles, Jimi Hendrix tripping on stage.
The 70s were weird and gave way to the even weirder early 80s. Blame cocaine for making everyone less cool. Things stopped making sense when David Byrne appeared on the scene. While the mainstream kids got swallowed up in a ridiculous sea of hair bands, the counterculture started digging the Talking Heads. It was at this moment, I believe, when your stereotypical, modern-day hipster was born. Now eccentricity became desirable. You could wear goofy glasses and clothes that didn’t fit, as long as you threw around the word ironic (regardless of whether you understood its definition).
With the 90s came Kurt Cobain and flannel. For whatever reason, he detested mainstream success and offed himself for selling out. Because cool implies exclusivity, once too many people like you, you’re no longer hip. While this may be common knowledge, it’s a stupid mindset. Snoop Dogg sold out but is still super suave.
And now, in the 21st century, we are left with a fragmented society in which Johnny Depp is admired for wearing crazy hats and leather flair. The kids in Brooklyn and Wicker Park grow beards and ride bikes and don’t eat meat because beef isn’t green, but cool remains a subjective abstraction. Pinning it down is impossible.
In conclusion, I leave you with this exchange from America’s most culturally relevant family:
Homer: So, I realized that being with my family is more important than being cool.
Bart: Dad, what you just said was powerfully uncool.
Homer: You know what the song says: “It’s hip to be square.”
Lisa: That song is so lame.
Homer: So lame that it’s… cool?
Marge: Am I cool, kids?
Marge: Good. I’m glad. And that’s what makes me cool, not caring, right?
Marge: Well, how the hell do you be cool? I feel like we’ve tried everything here.
Homer: Wait, Marge. Maybe if you’re truly cool, you don’t need to be told you’re cool.
Bart: Well, sure you do.
Lisa: How else would you know?