Recommended Book: A Naked Singularity by Sergio De La Pava
- Dina
- Apr 17
- 3 min read

I'm such a sucker for enormous postmodern doorstops like A Naked Singularity by Sergio De La Pava. He self-published this cinder block of a debut novel in 2008, but then it got picked up by The University of Chicago Press and went on to win the PEN Prize for Debut Fiction in 2013. I’ll be honest; it took me about six months to get through this 700-page hairy monster, but when I returned several months after reading the first 200 pages, I remembered exactly what was happening, who was talking, and what I had been anticipating, which is absolutely not something I can say for most books.
Many have likened the prose in this book to David Foster Wallace, DeLillo, Pynchon, and other writers of big fat books. De La Pava has his own style, though, focusing more on extremely lengthy dialogues (Gaddis-like, if you must compare) that I'm sure initially excited some screenwriter out there until he set the book down and thought, "Haha, there's no way in hell this would translate to the screen." Unfortunately, they did make a movie out of this. It did horribly, so let’s face it, there are some books you just can't adapt, OK? Just stop it, Hollywood.
But the novel is fantastic. It’s wild, loose, cerebral, heartbreaking, and completely inhabiting that paradoxically unrealistic but yet too-real world fiction can supply us. It’s (roughly) about a young and too-smart public defender in Manhattan and the various misadventures he gets drawn into out of both happenstance and his own hubris. The courtroom and jail scenes are hilarious and frustrating and the family scenes are authentic to the point of autobiography. There’s an enormous information dump about mid-1980s middleweight boxing heroes centering around Wilfred Benitez that was quite comforting to me because I'm the kind of gal who likes to kick back and watch old UFC fights and longform video essays on lineal titles. Some have called this a heist novel, but it’s only once you’ve crossed the halfway point that the characters even start talking about the idea of it, and then the insane final chunk of the story explodes into a breakneck kaleidoscope, giving everything it has to tick off the postmodern fiction criteria boxes that I learned about in skool so many years ago.
But lemme slow down and zoom in on one example of why I love this book: there's a particular dream sequence (and I usually hate dream sequences) that absolutely gutted me, it felt so true. It's on pages 456-463, and it's a hallucination the main character Casi has while on a plane. He’s exhausted and drugged up and as he's watching the in-flight movie without its soundtrack. His brain fills in the actors' words, inventing a whole narrative where two characters explore an extremely specific and profound kind of existential grief. The scene has nothing to do with the overall plot of the novel, and I think that's part of why I love it so much. As someone who spends so much time reading short fiction, I crave getting utterly immersed, lost even, in a jungle of a book like this, one where these digressions fill whole chapters and add nothing to the plot but everything to the tone and themes. You can't get away with that in most fiction.
Another reason I relished this hallucination scene is that it does what so many try to do with straight-up philosophical jabber (of which this book has in spades, don't get me wrong; there’s lots of the kind of chatter you’d have while smoking a joint out someone’s dorm window). It illustrates a complex abstract concept through narrative. The characters Casi dreams don't reappear, but I feel like the whole 700-page book wouldn't feel complete without these seven pages.
I recommend this book for people who like insanely long postmodern experiments that are richly satisfying and reward you for your time and devotion—or for anyone up for a challenge. Not everything in life should be easy. To hell with immediate gratification. To hell with the tik-tok'd attention span. Read a big weird book, dammit.