A Wannabe-Hardboiled-Jew Reads Raymond Chandler’s ‘The Long Goodbye’

It’s a long drag back from Brooklyn and one of the dullest in the city. Sometimes I’ll catch myself narrating life to myself this way, like I’ve just flicked away my cigarette, pulled up my collar, like I can still feel the day-old hangover crawling around silent and sluggish in the back of my head like a bad dream, and oh my God I’m doing it again, aren’t I? But that’s just the price we pay for reading The Long Goodbye.

I’ve read it almost half a dozen times. Certain chapters much more than that. And I’ve nearly memorized the last page, which, after all this time I still think is one of the best last pages ever written. And still, I don’t entirely know what to make of this book.

If Raymond Chandler’s earlier novels were detective stories that just so happened to be good, The Long Goodbye is a full reversal; it is a great novel that just so happens to be a detective story. It should be no different than saying Moby-Dick is a great novel that happens to be about whalers, or that Ulysses is a great novel that happens to take place in Dublin. But by describing it as detective fiction, we can obscure the fact for more than 60 years that it was one of the greatest novels ever written in America. There is hardly a novel more human, more heartbreaking, strung together with prose as boozily and as meticulously exacting as The Long Goodbye’s.

What I have realized is that, for one of the greatest noirs ever written, the investigation and the crime itself are almost boring, and that the book was busy doing something else all along, almost as if it were laughing at us for thinking it was just another pulp detective story. It tells the story of a missing person, the dead-end investigation for the motive of a suicide, of mistaken identity, and, of course, of backdoor shenanigans by powerful businesspeople. That part is formulaic.

The real story, however, to very sloppily paraphrase Raymond Chandler, is about the greatest mystery of all, the mystery that is the human heart, set against what is perhaps the greatest topographical enigma of all: The City at night. What could possibly be more uniquely American than rolling highway, dry wind up in the canyon, dim headlights refracting across the streets of Los Angeles?

If I can accidentally find myself narrating life in the voice of Marlowe, Raymond Chandler’s famous detective and the namesake of the next pet I get, it’s because The Long Goodbye captures all of America’s nastiness, all of its covert beauty. Sometimes when I read other Great American Novels (GAN©), I feel that the America described has already moldered into dust. What remains are traces, ideas. But Chandler could have been writing about America today, or America 100 years ago. He was able to sniff out certain things that are eternally American.

Marlowe is a sap. He can muscle through all manner of bodily harm but not a broken heart.

The Long Goodbye tells of the chaos that unfolds following an unlikely friendship between private dick Philip Marlowe and moneyed drunk Terry Lennox. It’s a friendship of gimlets, of each person recognizing that other has been burnt just the same way as they have. It’s the first time Marlowe shows a soft spot for another human being who isn’t a dame. One of the most powerful parts of this novel is the story of that silent understanding, that complicity that exists only in a deeply intimate friendship where nothing needs to be said, where judgment and frustration are always possibilities but never out of order. Where the friendship can end even when there is still love.

For Chandler, “hardboiled” doesn’t just mean tough—it means vulnerable at the wrong time. And in a sense, Marlowe is just a sap. He can muscle through all manner of bodily harm but not a broken heart. He can fall again and again for traps that each time lead to near-certain death. But he won’t allow himself to be duped twice by a friend.

It’s refreshing because I’ve felt at times (although I don’t like to admit it) that the American Tough Guy and his oppressive machismo is also oppressively un-Jewish. Jews are often his enemies and are fat with gold chains because—get it?—Jews like gold. But when Marlowe imagines himself drinking coffee and smoking a cigarette with his departed friend early one morning, he is doing something so elegiac that it can be matched only by saying Kaddish.

I have a theory that the great American Tough Guy is a myth—that he never existed and was dreamed up only to address some massive vulnerability in the national construction of self, almost like a superhero. Marlowe exposed him as a total sham. The brokenness that Marlowe carries, which is suggested but never addressed—a device that is the equivalent of gymnastics almost to the point of magic on Chandler’s part—is infinitely more American. The French can say bof all they want, and Italians have their mercurial shrugs and ironic, fatalistic hand gestures, but carrying brokenness to the point of near toxicity, for better although almost certainly for worse, is what we do in America, as Americans. That’s our thing. And Marlowe laid it bare for all the world to see.

As a Jew who has been searching for a chance at feeling hardboiled himself, I have at times tried to re-create moments from The Long Goodbye not only in my own writing but in my life as well. I have gone to a bar, like Marlowe, to sit and think after someone has left my life and ordered two drinks—one for me, and one for him. I have also tried playing chess at home by myself, but as it turns out I am exceptionally bad at chess, and I also find the game somewhat boring. But the truth remains that this book is so much a part of me that some element of my self-actualization will forever exist only in fantasy; that at times I can only be my truest self when I am not me, but when I am playing Phillip Marlowe.

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Read Alexander Aciman’s Bookworm column in Tablet magazine on Mondays.