Study Guide

The Crying of Lot 49 Introduction

By Thomas Pynchon

The Crying of Lot 49 Introduction

Pynchon called his novel The Crying of Lot 49 "a short story, but with gland trouble." Basically, that means it's a really fat short story. Welcome to ThomasPynchonTown—wordplay is king around these parts. And because this novel is basically a super-chubby short story, it's basically impossible to fit it all into a nutshell.

But hey—after reading The Crying of Lot 49, we're up for any challenge you throw our way.

The Crying of Lot 49 was released in 1966 and was both a critical darling and a national bestseller…which doesn't happen a lot. It's the story of a (yup, desperate) housewife named Oedipa Maas who, in attempting to take care of her ex-boyfriend's will, uncovers what may be a centuries-old conspiracy called the Tristero—a radical group opposed to government monopolies on mail. The plot is super-complex, and what makes it even more challenging is that Oedipa is not sure if the Tristero is real, or if she is crazy and is simply imagining the whole thing, or if her ex-boyfriend is just playing an elaborate practical joke on her.

And—spoiler alert—we never know either. Again: welcome to ThomasPynchonTown, Population: One Trillion Confused Readers.

The reader of Lot 49 is put in pretty much the same position as Oedipa Maas: desperately trying to untangle the mystery, while simultaneously wondering if the whole thing is just a big practical joke. Like other Postmodern authors writing around this time, Pynchon turns the traditional art of storytelling on its freakin' head and plays metafictional games that allow him to question the role of language in our lives… as well as the nature of fiction.

But if Pynchon's novel was only a hi-larious practical joke, it wouldn't have aged as well as it has. Pynchon wrote the book in the middle of one of the most turbulent decades in American history: the 1960s. And this book is as insane as that decade was.

What Pynchon does in The Crying of Lot 49 is hijack all of the most insane and genius techniques being used in modern fiction (lookin' at you, Postmodernism) and then gleefully crashes them into the world of 1960s counterculture. Pynchon parodies all of the major movements of the time, from extreme conservatism to radical liberalism to the zoned-out self-indulgence of California hippie and drug culture.

So what is this novel? Well, it's impossible to fit it in a nutshell, that's what. It's a postmodern novel, a social satire, a really in-depth look at 1960s California, the story of a housewife going insane and getting involved in conspiracy theories… and, quite possibly, also a huge practical joke.

What is The Crying of Lot 49 About and Why Should I Care?

Even though John Oliver thinks it's evil, there's nothing quite like a really good April Fool's Day gag. Maybe when you were a kid you put salt in the sugar bowl and watched your parents spit out their morning coffee. Maybe you put toothpaste on the toilet seat. Maybe you still put toothpaste on the toilet seat (you jerk). Or maybe you were never the kind of little devil that played pranks on other people… but you still wait with bated breath every year to see what other people have in store for you.

No matter which side of the April's Fool line you fall on—whether you love to prank or be pranked—The Crying of Lot 49 will deliver the tricksy goods. We think. Because this novel is either an insanely elaborate practical joke or a riveting and genius dissection of the American Dream gone very, very wrong. Or—hey—it might be both. That might, in fact, be the trick.

If you're the kind of person who loves to check out the ridiculousness that Google delivers on April 1st and wonder if a SelfieShoe is a real thing, if you think absurdist humor is hilarious, and if you think a good hoax is as good as the best reality, then you'll love this deeply strange novel. Because this novel could very well be nothing more than Thomas Pynchon laughing at you, the reader, from behind his typewriter.

And hey—if you're the kind of person who likes to be the prankster, read this novel and hand it to your most pretentious lit-snob friend and ask them "What is the significance of Oedipa Maas' name?" or "Tell me about Tristero" and watch them sputter and get pompous. And then laugh at them because you know that The Crying of Lot 49 might be just an elaborate practical joke.

But what if you're neither a jokester nor a happy recipient of jokes? What if you like your novels to be Super Serious? Well, Shmooper, you're still in luck. Because this book is way more than just (probably) a huge joke at the reader's expense. It's also a sharp satire about sex, Jacobian plays, the Mafia, the postal service, American history, and drugs. This novel is, in short, one of the best explorations of America during the 1960s counterculture. Ever.

If this all sounds intriguing, then it's time to dive into the hilarious, perverse, and brilliant mind of Thomas Pynchon. Sure, Jack Kerouac was a nice guy, and William S. Burroughs managed to write a book while whacked out on junk. But Pynchon leaves those two guys in his wake. He is the great novelist of the American counterculture.

The Crying of Lot 49 Resources


Lot 49 Wiki
The Lot 49 page from a large Wiki put together by fans of Pynchon's work. Yup: Pynchon is complicated enough to need his own Wiki.

Articles and Interviews

Embattled Underground
The original New York Times review from when Pynchon's book came out. It's even more complicated than the book itself.

The Satirist
A slightly more critical (and down-to-earth) review of Pynchon's book.


Ducking the National Book Award Ceremony
A video about how Pynchon had an actor speak for him when Gravity's Rainbow won the National Book Award in 1973.

Pynchon on The Simpsons
Though Pynchon is a famous recluse—and hasn't done an interview in years—that didn't stop him from agreeing to a brief cameo on The Simpsons. Priorities, man.


Lot 49 Lecture
You don't have to go to Yale to hear what one of their English professors thinks about Thomas Pynchon's book.