Don DeLillo used to be funny. Like, laugh-out-loud hilarious. I’m not sure what happened after that.

My story is typical, I think: DeLillo lost me from Underworld onwards. I read The Body Artist when it came out and it did nothing for me, nor did Cosmopolis. I got maybe a quarter through Falling Man before I stopped and left it alone, and didn’t even get that far with Point Omega. I will freely admit regarding DeLillo – as I would with once-favorite bands like Sonic Youth and Soundgarden and Pavement, or even authors like Philip Roth and Thomas Pynchon – that the lack of interest in later works is not that I found those works inferior. They just didn’t speak to me the way the earlier stuff did, they did not find me at that stage in my life when their work would most matter and imprint on me. So it’s me, not them. Nevertheless, the bias remains.

So when I picked up The Angel Esmeralda: Nine Stories, I wondered: could I find something I’ll enjoy? Is there magic in this collection that will remind me of what I love about DeLillo? Would I find early-to-mid DeLillo in short story form more engaging than late DeLillo in the same form? Or will my attitude to the author’s novels extend to his shorter works as well?

As I started reading, I realized this much: what didn’t work for me in the later DeLillo novels was definitely the lack of humor. Which isn’t to say that DeLillo’s pre-Underworld books were all laugh riots, but there was certainly a nuanced appreciation for the absurd and the surreal in many of the books before the current millennium. Cosmopolis seemed to have that, too, but it felt too claustrophpbic and self-important and contrived to pull it off properly. But End Zone, Ratner’s Star, and White Noise are all comedic novels, while the likes of Running Dog, Players, and Mao II had scenes that could make me laugh appreciatively in the face of DeLillo’s vaunted shamanistic American dread. So were such humorous concerns still in DeLillo’s short fiction wheelhouse? What would click with me and what would not?

As is often the case with DeLillo, this book is broken down into distinct parts, each covering a specific era in his writing career. So there’s an easy way to break down the stages and see if it goes astray, I thought.

Part One – we’ll call it the Early Years – has two stories. “Creation” is a trifle about a couple that is stuck at their vacation paradise and the mildness of the narration carries an angsty jocularity throughout. Nothing in particular stands out about it. “Human Moments In World War III” is very funny by the end and is definitely in the spirit of End Zone and Ratner’s Star. The premise is intriguing: two astronauts in a space station float above the Earth while they bear witness to what may be the start of an international crisis. The astronauts deal with the routines and protocols of the space station, but also have to deal with each other and their Odd Couple roommate quirks (this is what most reminded me of End Zone). The story manages to be morbid and funny at the same time, struggling with monotony and the threat of humanity’s end in alternating doses. Is there a big payoff at the end, some slam-bang cataclysm? Not quite. But as an interlude at a strange moment in imagined history, this is definitely a keeper.

Part Two – let’s call it the Middle Years – has three stories. “The Runner” and “The Ivory Acrobat” are about individuals dealing with precise moments of crisis in very specific locales: a runner who witnesses a crime in Central Park, and an American teacher who is traumatized by earthquakes in Greece. Both stories are solidly crafted and make for good diversionary reading. Both also feature some wry dialogue between characters that are mildly funny but not laugh-out-loud. “The Angel Esmeralda” is probably the best known of DeLillo’s short stories, I think it was part of Underworld but I’m not positive on that. Anyway, it deals with a nun living in New York City and having to deal with the daily tragedies that occur in her struggle to be a light of good and virtue in the face of decaying moral disintegration. There is a dry wit that runs throughout this story, mostly from Sister Edgar’s attitude to the modern world and especially the way she makes peace with the world of sin she is forced to tolerate and make right. And I actually laughed out loud once, at Sister Gracie’s description of chasing Esmeralda and running into bats. It’s a wonderful bit of dialogue that has a verve and energy that makes it sing. It is the only solid story of the trio in this section, and it may not have been funny but it has a poignant power and beautifully-crafted prose that the other two severely lacked.

Part Three – which we can call Late DeLillo – took me a while to work up to. These were the years, after all, when I had given up and stopped caring. I wasn’t in the right frame of mind for the four stories in this section, or so I thought. That said, two of the stories in this section actually offered some surprising knee-slappers.

To get the dour news out of the way, I was less than thrilled by “Baader Meinhof” and “The Starveling”. Both offered beautifully crafted prose, and both felt very… urban, I guess. The sense of place was strong in both stories, one got a sense that they were about life in the city, and “The Starveling” felt almost like a love letter to New York City in all its gritty idiosyncracy. That said, I found the city interlude of “Baader Meinhof” to be purposefully joyless: a woman is admiring a series of paintings depicting the deaths of the ringleaders of the notorious Baader Meinhof gang, and while doing so has a chance encounter with a fellow museum goer. It does not go well from there. “The Starveling” left me a bit puzzled, even confused. It’s my fault, I just could not commit to the story and skated along with the prose instead. I dipped in some nostalgia for the NYC of my youth. Otherwise, the story seemed to be about a couple, one of them an actress struggling o find work, and how they both tried to maintain the relationship together. It reminded me a little of The Body Artist, but that just made my mind glaze over as I slogged through. I was glad when it was over, but I felt my suspicions confirmed.

“Midnight In Dostoevsky” was lighter, even refreshingly amusing in some ways, as it follows the friendship of two young college students who like to challenge each other intellectually with random arguments and a kind of hero worship for an obscurantist logic professor. The two friends become enthralled by the mystery of an old man in a heavy winter coat – one of their mindful jousts is over exactly what kind of coat he is wearing – and they become a bit too obsessed with the old man and what his truth is. The conversations between the students is cause for sharp, playful dialogue which also somehow lives up to the notion of being sophomoric – that is, wise fools – and earnest all at once. There is a brief exchange between one of the boys and a female student in the logic class, which sparkles nicely and adds to the mystique of their professor. But ultimately, the story is about taking a pointless distraction and pushing it too far. It could be an allegory about the price of being too geeky, but doesn’t offer much depth to make me stop and pause.

The real jewel, though, was “Hammer and Sickle”. If there was more late DeLillo like this, then sign me up for more: this story manages to be hilariously funny while also being laden with dread and biting commentary on the state of our culture. Basically, a man serving time at a Club Fed styled prison finds out that his wife is using his two daughters to give international financial news reports. And that’s about it. Except the way these two girls provide these news highlights the strangeness and absurdity and randomness of the high stakes world of finances, which is both cute because it’s kids but also frightening because it makes plain just how absurd world economics have become. There is a joy and a growing sense of un-ease to simply read the recitations of these children as they talk of important things, a rhythm and poetry that makes it both awe-inspiring in craft but also resonant in its clear mischievous delight.

And in essence, this is what makes DeLillo unique in his finest and funniest moments. What he does is he takes the languages of a complicated, consequential world – be it the latest market news or the handling of a spaceship or the bantering of academia or the evacuation of an airborne toxic event or the tactics of armageddon – and basks in its jargon, in its minutiae, in the sheer luxuriance of specific words uttered and precise knowledge mastered. In such a loving, perhaps even fetishistic, play with this language of importance, DeLillo manages to freight it with a subtext of existential panic, of using these specific terms and conditions to hide the fact that our world is slowly, inexorably descending into a sinkhole of shit. It is the modern cultural equivalent of moving the deck chairs of the Titanic, but done as a precise Bob Fosse-sequel ballet that is achingly beautiful despite the futility it tries to mask. And that, best as I can figure out, is what makes it both hilarious and dreadfully terrifying.

It is the knowledge that we seek to distract ourselves from forces that we cannot control but which threaten our sense of security, that undercut the values that we hold dear. “Hammer And Sickle” not only has the children reciting the news call for a proletariat revolution as late capitalism grinds into an economic apocalypse of its own making, but the narrator sees his family crumbling under the aegis of a vengeful wife and uncaring children, more concerned about pronouncing foreign words and making agitprop chants than showing any real concern for the paterfamilias that has betrayed them on the throne of Mannon. That is what makes this story sing, that is what makes it both unbelievably funny and heartbreakingly sad, and this is a story I can see myself returning to time and again, if only to bask in the wordplay and its surreal implosion of the significance of these worldly matters.

So I must confess, I was surprised that I do indeed like some late DeLillo, albeit a work that may seem minor and brief to others. Nevertheless, “Hammer And Sickle” sparkles with a ferocity that I savor, and this makes me want to go back and read some more of the older wit and wisdom of DeLillo, probably starting with End Zone and working on from there. And I will likely bask in “Hammer And Sickle” a few more times, just because it makes me laugh out loud – and in this day and age, a good laugh is something to always treasure.