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Seven times Jack Kerouac was too cool for you squares!

Jack Kerouac. Rebel. Icon. Visionary. He is all three of these things to a handful of teenage white boys who see pot as so taboo that they think it’s an act of rebellion to smoke it. Yes old Jackie Jack was putting a middle finger up to the man (in a safe, marketable way) while the likes of David Walker and Emma Goldman were busy being dead, those squares, and while the likes of Mandela were also being squares but alive ones. Kerouac’s On the Road is now considered one of the most important pieces of literature, reading like Ayn Rand suddenly discovered a truckload of weed and decided to lecture people on how being selfish and high was cool instead of her usual lectures on how being sober and selfish was cool. But it’s difficult to talk in generalities. Here are seven exact examples of how much cooler The Kerou-batman was than you squares!

1. When he kept using terms like ‘cool cats’ and ‘skiboppody boo-bip’ even though it obviously made him sound like a total twat

The English language is ever evolving, and slang is a constant part of that process. Many aspects of slang come in and out of favour, and many pass over to the next generation. Not so the slang of the Beat Generation because it is just so fucking stupid and nobody should have ever thought otherwise. But Jack ‘talk smack’ Kerouac was so cool that he could use it even though it was clear that everybody would laugh at him even while it was in use. Yes, whether he was talking about girls with the shiny eyes, or calling every person a cat in the (mistaken) belief that he had some kinship with the jazz movement, Jack and the Beatstalk was just too awesome to ever stop using that. Take that squares!

2. When he was visibly impressed by a guy drumming on his steering wheel

One of the cooler aspects of Jack ‘Release the Kerouackan’ is his self-destructive devotion to Neal Cassady, a narcissistic douchebag who unthinkingly destroys the lives of the people around him. What inspires such devotion? If we’re to believe On The Road, Cassady (as Dean Moriarty) does things like drumming on a steering wheel and talking about the music of the universe. Jack ‘I’m on Crack-o-rac’ then treats this as though it’s the deepest shit he’s ever heard and not something that literally every high, drunk, or slightly light-headed person has said at one point or another, because unlike you squares he’s cool.

3. When he tried to make the Six Gallery Reading all about him, because the concept that something was happening and he wasn’t the centre of attention filled him with a sense of deep existential dread

The six gallery reading was an historic event when Allen Ginsberg first unveiled his poem Howl. This was a few decades before Ginsberg openly endorsed pro-paedophilia organisation NAMBLA, so he still seemed pretty cool and this reading was his big moment (and there were a bunch of other people reading too. Who cares). Seeing this, Jack ‘Panic Attack-ourac’ decided that the people in this establishment were too square and went to get some liquor-o-bop to skeev those squares down (or up. Who cares). Then he repeatedly shouted at Ginsberg during the performance, probably saying things like ‘It’s me, Jack Kerouac, they call me ‘The Tiger’ for my tiger like qualities’ and ‘Hey, Allen, I’m scared that if I stop talking I’ll die!’ Once again, way cooler than you squares.

4. That time he had sex with a Mexican

One of Jack ‘I definitely have a six-pack’ Kerouac’s most consistent qualities is his conviction that all women, whether they’re walking along minding their own business, actively making out with his best friend, or existing somewhere on the other side of the earth, are all hungry for a Kerouac-a-snack. Sometimes he was even right, and he once had sex with a Mexican which was the raddest shit ever to him. Calm down Jack! We can’t keep up with your rebel ways!

5. That time he spontaneously wrote a novel in a few days after about ten years of writing draft after draft and making meticulous plans for the novel

Jack ‘ahead of the pack’-ourac wasn’t just a super cool guy who drank and shouted at people. He also told everybody who would listen that he wrote ‘On the Road’ as a stream of consciousness thing over several days of non-stop work! This was total bullshit, he’d been writing drafts and planning it for about a decade, so technically it was a way longer and more intricate planning process than many novelists, but only somebody really cool would feel the need to lie about something so utterly banal just to seem cool! NO YOU’RE A SQUARE!

6. Those times he took drugs

None of you squares know what drugs are. Jack ‘clackity-clack, let me across the bridge I’m the biggest goat’ Kerouac sure did though. He took them! Take that squares!

7. That time he challenged the other Beats to a balloon race around the world, and they were like ‘chill the fuck out Jack, we’re trying to do something nice for Gary Snyder’s birthday’, and then he cried for a solid hour because he thought they didn’t like him anymore

This definitely happened and it was wonderful.

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