The mill of time grinds everything, but it doesn't grind equally. You might think that a more-or-less conventional metafictional guy-writing-a-novel book would date more gracefully than a bizarre unexplained fantasia that eventually comes into focus as an afterlife fantasy. You might think that
especially when the first was mildly successful for the author on its publication, and the second, despite his best efforts, was not published until the year after his death.
You might think that. But, in this case, the conventional wisdom is against you, and you would actually be wrong.
"Flann O'Brien" was one of a number of pseudonyms - I gather vaguely transparent, at least to the literary establishment he was part of - used by Dublin writer Brian O'Nolan for a little more than a quarter of a century, starting just before WWII. O'Brien was the novelist; "Myles na gCopaleen" wrote a daily slice-of-life column for the Irish Times; O'Nolan in his regular life was a civil servant. I'll just use the O'Brien name from here on for simplicity.
O'Brien's work, in newspapers and novels and plays, seems to have always been mildly satirical - he first gained fame by shoving his way into a literary feud in a "let's you and him fight" way that seems very characteristic. I think he had the born newspaperman's love for celebrating "regular people" and of lampooning the powers of the day, wedded to a fairly radical sense of what writing could be and do. The two novels of his I've read are both the kind of thing that could be called "experimental," even eighty years later.
I'm no expert on the period and the milieu, but I think I see a tension between a generally conservative moral outlook and view of the world - it was Dublin in the mid-20th century, which was a pretty conservative place to begin with - and a more radical impulse in creating stories.
So O'Brien's first novel was At-Swim-Two-Birds, a metafiction about a novelist writing a novel about a (radical, modern) novelist whose characters revolt at all of the horrible things they are made to do and take over Novel #2, while the top-level Novel #1 is mostly about the main character not writing. It's been called one of the funniest ever written, but - and this is the part I'd emphasize - primarily by men from Dublin who lived roughly contemporaneously to O'Brien. It is still funny, but it's also deeply obscure to those born and raised elsewhere and elsewhen.
O'Brien's second novel, finished in 1940 but not published until 1967, after he died on the previous April Fool's Day, is the even weirder The Third Policeman. It's narrated in the first person, by a man just as nameless as Swim's narrator (though they couldn't be the same person). It was also meant to be funny, and I found - perhaps because it was so odd and quirky and of-itself to begin with - it's still funny in the same ways, even for radically different audiences. It starts out in crime-fiction mode, with the narrator explaining admitting that he murdered the miser Philip Mathers, but first wanting to explain his life up to that point.
He was the son of a farmer and a tavern-owner who both died when he was young, and, was then sent away to school, where he developed an interest in the famous writer and thinker de Selby. As a young adult, he returned to his home, which was being managed and run by the tenant farmer John Divney. And then he spent some number of years just living there, with Divney still running the operation - and, clearly, sponging off whatever money was generated - while the narrator mostly just sat in a room, working on a massive concordance to the commentaries on de Selby.
That point is characteristic of O'Brien, so let me underline it: our hero's massive project is not original work, or even commentary on the famous work of another, but a third-level reference work that organizes other people's thoughts and writings to make them easier to navigate.
Anyway, this all gets covered very quickly, and the narrator grows into middle age. He and Divney - mostly Divney - concoct a scheme to kill and rob Mathers, which they then do. Divney runs off with the cash-box and hides it somewhere, leading to several more years of the narrator never letting Divney out of his sight. Finally, Divney tells the narrator where to retrieve the cash-box - under a specific floorboard of Mather's old house - and Chapter Two begins with the narrator having grabbed the thing he found under that floorboard.
The novel really starts there: the narrator has an odd conversation with the claims-not-to-be-dead Mathers, and emerges into a surreal landscape that is similar to his homeland, but somehow different. He travels down roads unfamiliar to him and meets the bicycle-obsessed policemen in charge there, eventually being charged with the murder of Mathers - who, again, he last saw alive, and who has supposedly been murdered in a different way.
Surreal events pile up, a gallows is built to execute the narrator, but he manages to escape with the aid of a band of one-legged men led by the bandit Martin Finnucane and makes his way back to the house where he lived with Divney.
And, yes, after Divney is shocked by the narrator's return, the reader is told that the narrator is dead: the "cash-box" hidden in Mathers' house was a bomb, and the narrator was blown up there. The policemen, their bicycles and station-houses, and the whole surreal world of most of Third Policeman, is actually Hell and the narrator is being tormented eternally for his sin.
To be clearer: the "this-is-Hell" is implied, but the edition I read - and, I gather, editions of Third Policeman generally - include letters from O'Brien explaining that, since the fact that the narrator is dead is entirely clear, but the rest of it has to be implied. (Though, I suppose, if you're Irish in 1940, a dead murderer could only be one place.)
This is a deeply weird - in most of the literary senses of that word - and amusing novel. Let me quote one bit, from pp.324-5 of the edition I read (an Everyman's Library omnibus of The Complete Novels) as an example. If this amuses you, you'll like The Third Policeman:
I opened the bed fastidiously, lay into the middle of it, closed it up again carefully and let out a sigh of happiness and rest. I felt as if all my weariness and perplexities of the day had descended on me pleasurably like a great heavy quilt which would keep me warm and sleepy. My knees opened up like rosebuds in rich sunlight, pushing my shins two inches further to the bottom of the bed. Every joint became loose and foolish and devoid of true utility. Every inch of my person gained weight with every second until the total burden on the bed was approximately five hundred thousand tons. This was evenly distributed on the four wooden legs of the bed, which had by now become an integral part of the universe. My eyelids, each weighing no less than four tons, slewed ponderously across my eyeballs. My narrow shins, itchier and more remote in their agony of relaxation, moved further away from me til my happy toes pressed closely on the bars. My position was completely horizontal, ponderous, absolute, and incontrovertible. United with the bed I became momentous and planetary