davidaguilarrodriguez 's review for:

The Crying of Lot 49 by Thomas Pynchon

4.5

challenging funny mysterious medium-paced

Plot or Character Driven: A mix

Strong character development: Complicated

Loveable characters: No

Diverse cast of characters: No

Flaws of characters a main focus: Complicated

---

Update: This book was a little mixed for me on first read, but I have been thinking of it ever since, so I raised my rating. This one maybe takes some time to simmer.
 
I think if this had been my first Pynchon book, it probably would have bounced off me and I wouldn't have come back for more (to my great loss, because I actually really like him). But having read Vineland and gotten Pynchon-pilled, I was mostly able to enjoy the ride. I guess what I'm saying is that I think this book is good, but I wouldn't start here with Tommy P.

Crying of Lot 49 feels like an adrenaline shot of everything Pynchon does well but also everything he struggles with. The paranoia-conspiracy plot is intentionally abstract, the characters are thin and mostly symbolic, and the whole thing walks a fine line between brilliantly funny and narratively frustrating. But that’s kind of the point. It’s about entropy, communication breakdown, and the desperate need to assign meaning even when it may not be there. Or worse, when it might be — just out of reach.

I love Pynchon’s prose and humor in general, but this is probably my least favorite distillation of it. In his longer, shaggier works (Vineland, Mason & Dixon), there’s room to breathe — to let the jokes and absurdism unfurl, to build character, to let the weirdness accumulate until it starts to feel mythic. Crying of Lot 49 is wound too tight. It is clever, dense, carefully constructed -- definitely way tighter and sharply focused, but also less fun for it.

That said, the zany moments absolutely sparkle: the Nazi rooftop therapist Dr. Hilarius, the bathroom stall Tristero symbol, the play-within-the-novel, the weird songs and names. Pynchon is brilliant at building webs of paranoia and meaning but also making it silly and funny, rather than just heavy and relentlessly dark. 

What is this book about? Everything and nothing. America. Madness. Lost mail routes. The deep fear that someone, somewhere, knows something you don’t — and that everything might be connected, or maybe you're just losing your mind. It’s prescient in a way that feels eerily in step with today’s online conspiracists and post-truth chaos. It's the book-length version of the Charlie Day Conspiracy Board meme or the classic Nirvana lyric: Just because you’re paranoid don’t mean they’re not after you.

This isn’t my favorite Pynchon — the lack of emotional resonance and fully realized characters holds it back for me. But it’s smart, sharp, and occasionally hilarious. A young man’s brilliant literary and philosophical pyrotechnics. Not as wise or generous as his later work, but still good.