Notes from the Underground

★★★★★ – “I Am a Sick Man. I Am a Spiteful Man. I Am, Apparently, Hilarious.”

Dostoevsky’s Notes from Underground is a masterclass in misanthropic soliloquy — part philosophical treatise, part psychological farce, and altogether one of the most darkly entertaining monologues I’ve ever had the guilty pleasure of eavesdropping upon. It’s a screaming match between Enlightenment rationality and the petty, pulsing irrationality of actual human life — and guess who wins? (Hint: not the utopians.)

Audio: NotebookLM podcast on this topic.

The first part, a searing, feverish diatribe, reads like the diary of a man who’s been locked in a room with too much Hegel and not enough human contact. It’s Dostoevsky’s pre-emptive strike against every social engineer who’s ever said, “Well, surely man will behave if we just fix the plumbing.” The Underground Man begs to differ — loudly, neurotically, and with an almost Shakespearean flourish of self-abuse.

But it’s the second part — Apropos of the Wet Snow — where things truly fall gloriously apart. Here the theoretical gives way to the tragically tangible. Our narrator, more unhinged by the page, lurches into society like a moth into a bonfire — vengeful, humiliated, self-aware to the point of paralysis. His disastrous encounter with Liza is almost unbearable in its sincerity and cruelty, a pas de deux of hope and destruction that left me squirming and spellbound.

What surprised me most was the humour. Not the cheap slapstick of caricature, but the agonising, close-to-the-bone absurdity that arises when a man is too clever to be functional and too self-aware to change. The Underground Man doesn’t just dig his hole — he drafts blueprints, writes footnotes, and criticises the soil quality.

As a companion read, Tolstoy’s The Death of Ivan Ilych provides a poignant counterpoint. Where Tolstoy charts the steady, ghastly march of bourgeois conformity towards a deathbed revelation, Dostoevsky gives us a man already buried in his psyche, clawing at the dirt and calling it philosophy. Ivan Ilych dies trying to make sense of his life; the Underground Man lives trying to make death of sense itself.

Together, they are a fine Russian reminder that being alive is no guarantee of being well — or even remotely rational.

—don’t let him wander.

My biggest problem with generative AI is its lack of subtlety and misunderstanding of satire and irony. I am writing a short story, and a character is calling an emergency number. I shared the first scene with Grok, and it suggests that I turn the absurdity up to 11 and replace this segment with the one above:

“Okay, ma’am. Can you stay with him? I’ll dispatch an ambulance to your location.”

It is funny in its way, but I’m only pretty sure that an operator would not be injecting humour into a situation where a woman is reporting an unconscious person. Absurd doesn’t need to be Monty Python funny.

Am I being too critical?

Audio: NotebookLM Podcast discusses this issue.

More to the point, I find that many humans miss subtlety. Many people need every storyline highlighted and retraced with a bold Sharpie. Every detail needs to be explained because they can’t connect the dots. This is reflected in the cinema, television, and books of the past half-century or more, so is it fair to criticise AI for being dull when it’s at least on par with more than half the human population.

Are we asking AI to be held to a higher standard?