Tuesday, April 21, 2026

The Long Goodbye by Raymond Chandler

Source of book: I own this

 

This book ended up being the choice for both of my book clubs. Our local in-person one read it for last month, but I was unable to attend due to a concert. (This spring has been insanity - I said yes to a lot of gigs, and have been pretty busy on weekends.) We also picked it for my online club - three of us read and discuss at our own pace. 


 

I read The Big Sleep last year, so it was interesting to compare the two books. The first one was an early work, while The Long Goodbye was a later one. There is definitely plenty of contrast between the two. 

 

First is the climatic setting. The Big Sleep is all about the winter rain. It feels like it rains constantly, in that southern California way. In contrast, The Long Goodbye occurs in a humid, smoggy summer, the kind that I remember from my childhood.

 

In addition, this book mostly takes place in the San Fernando Valley, which is where I grew up, so it felt even more familiar than the central Los Angeles setting of The Big Sleep. Specifically, it is set in and around Encino, although time has sure changed things about the area. 

 

[For those who care, “Sepulveda Canyon” is referenced several times. This is now where the infamous Interstate 405 goes through the pass, but back then, it was relatively rural, and could very well have had a shady alcohol “rehab” place tucked up in the hills. Likewise, the area around the Encino Reservoir no longer has large lots - it’s pretty built up - but is still hella expensive.]

 

The book is also longer than the other books Chandler wrote, and I think it was for good reason. The Big Sleep is classic Philip Marlowe detective noir - straight up and to the point. Marlowe avoids emotional entanglement, acts with confidence, and solves his case. 

 

The Long Goodbye feels different. This is an older Marlowe, more jaded but also less sure of himself and his business. We see so much more of him as a human. The writing is far more introspective. No shade on the earlier novels, but this one is closer to literary fiction. 

 

Don’t get me wrong: this is still detective noir, and if you want a banger of a mystery and the usual gumshoe investigation, shady characters, dangerous women, dissipated men, and the rest, it is all very much there in this book. 

 

But there is a thoughtfulness in the book too, and I think we see a lot more of Chandler himself showing through. 

 

I find it interesting that some critics considered it an inferior book, but I don’t see that at all. The social criticism, inner life, and more nuanced situations make for a stronger - and deeper - book. 

 

Also, this book has rightly raised some questions about Chandler’s sexuality, due to its homoerotic undertones and autobiographical elements. Indeed, all of Chandler’s books have homosexual elements, overt and covert. And also plenty of homophobia. 

 

What do we make of Chandler? He married a woman nearly two decades older than himself, and the relationship was reputed to be more platonic than not. He didn’t have any documented relationships with men, but even during his lifetime there was talk. Was his a lavender marriage? Was he an asexual? (That’s also plausible, given how he writes about sex.) 

 

What I can say pretty confidently is that he does not write like an allosexual heterosexual. At all. More like someone cosplaying what he thinks heterosexuality looks like. 

 

Before I jump into the book itself, I also want to note that all of Chandler’s books show their age when it comes to stereotypes. The casual racism and sexism (and the homophobia mentioned above) is jarring, even though it was common at the time. Perhaps the Asian stereotypes feel the most out of place, because anti-black racism and misogyny are on the rise in the Trump era, and so feel more familiar. 

 

So, as with any book, recognize the bad, embrace the good, and be aware that our own blind spots aren’t visible to us, but will be to subsequent generations.

 

On the far better side, Chandler’s books - particularly this one - illuminate just how horrible the ultra-rich are. Wealth corrupts the soul - one of the key teachings of Christ, by the way - and love of money is the root of pretty much every evil. It is no accident that the ultra-rich gravitated to Jeffrey Epstein and the rape of young children. That’s what obscene riches create. Every time.  

 

The book has plenty of social commentary about crooked cops, economic inequality and the way it perverts justice, materialism, and the illusion of the American Dream. Classic 1950s stuff. 

 

Now, about the story. It starts with a crazy scene. Marlowe discovers a drunk-out-of-his-mind man outside a club. He notices a huge scar on the man’s face, and is somehow drawn to him, so he takes him home to sleep it off. 

 

Yeah, this already seems to have some gay undertones to it, right? Anyway, this man, Terry Lennox, is one of two characters in this book that have some autobiographical elements. Like Terry, Chandler had a big drinking problem, periodically blackout binge drinking and nearly killing himself. 

 

Anyway, the two men become casual friends, meeting for drinks occasionally. 

 

But then, one night, Terry shows up at Marlowe’s house, and asks him to drive him to Mexico. Marlowe, in what has to be terrible judgment - or perhaps being in love? - does so, but refuses to hear any story, because he doesn’t want to be an accessory if something bad went down.

 

When he returns, he discovers that Lennox’s wife has been brutally murdered, Lennox is the suspect, and that the police think he was an accessory. 

 

Well, what they really want is for him to give his information so they can find Lennox. 

 

Again, inexplicably, Marlowe refuses to talk, spends some time in jail, and is only released because the victim’s father pulls strings. 

 

Again, everything makes a lot more sense if Marlowe is in love with Terry. 

 

So anyway, word then comes that Lennox has committed suicide in Mexico, leaving behind a written confession. 

 

But Marlowe isn’t convinced that Terry did the crime, and also suspects that the “suicide” was either a murder or a fake. And so, he proceeds to do his own investigation into the situation. 

 

Meanwhile, he is also approached by a New York publishing agent, who has a pulp writer, Roger Wade, who needs to finish his promised book, but keeps falling off the wagon and doing crazy things. Hey, the other character based on Chandler!

 

Although Marlowe initially refuses the assignment, he eventually accepts after he meets Eileen, Roger’s beautiful wife. 

 

And, it turns out that all these people know each other: Lennox, his wife, her rich father, her sister and husband, the Wades. With the exception of the reclusive multi-millionaire father (a type that appears in multiple Chandler books), they all party together. (And the parties are damn tedious. Amazing descriptive writing - one suspects Chandler sat through a lot of these terrible parties.) 

 

Oh, and there are more of the usual characters. A gangster named Mendy Menendez, who seems to be connected to Terry. Various crooked and violent cops. Marlowe’s old buddy from the LAPD, Bernie. A creepy bodyguard (and possible boyfriend) for Roger. Doctors pushing quack cures and alcohol treatment. Doctors pushing illicit pills. And, of course, don’t ever trust any woman in a Chandler book. 

 

I won’t go any further with the plot, because, well, that’s part of the fun, right? It’s a good story, the twists don’t come out of nowhere, but are still surprising and satisfying. I thought it was a fun read. If you like detective noir, this is a good one. But also, it is a bit slower paced than other Chandler books - and there is a lot more introspection, which I like. 

 

With that, let’s look at some lines, because Chandler is all about the zingers, right?

 

The girl gave him a look which ought to have stuck at least four inches out of his back. 

 

My wife can give those looks. Generally not to me, but to guys who definitely deserve it.

 

In one of the weirdest passages, there is this reminder that some things have really changed over the years:

 

It was the week after Thanksgiving when I saw him again. The stores along Hollywood Boulevard were already beginning to fill up with overpriced Christmas junk, and the daily papers were beginning to scream about how terrible it would be if you didn’t get your Christmas shopping done early.

 

Wait, WHAT? These days, Christmas crap is in the stores by August, and the music starts playing everywhere after Halloween. We could only wish that it held off until the week after Thanksgiving. 

 

“I’m rich. Who the hell wants to be happy?”

 

And this line from a lawyer:

 

“You had to play the big scene,” he said coldly. “Stand on your rights, talk about the law. How ingenuous can a man get, Marlowe? A man like you who is supposed to know his way around. The law isn’t justice. It’s a very imperfect mechanism. If you press exactly the right buttons and are also lucky, justice might show up in the answer. A mechanism is all the law was ever intended to be.”

 

As a lawyer myself, I agree with that. The thing is, like democracy, as imperfect as it is, it beats the alternatives. 

 

Guys with a hundred million dollars live a peculiar life, behind a screen of servants, bodyguards, secretaries, lawyers, and tame executives. Presumably they eat, sleep, get their hair cut, and wear clothes. But you never know for sure. 

 

Yep. No contact with ordinary people except as employees. That’s part of what corrupts the soul. 

 

He hung up in my ear. I replaced the phone thinking that an honest cop with a bad conscience always acts tough. So does a dishonest cop. So does almost anyone, including me. 

 

Some of Chandler’s descriptions are so over-the-top they are good. 

 

Inside was a small and ugly reception room, but the ugliness was deliberate and expensive. The furniture was scarlet and dark green, the walls were a flat brunswick green, and the pictures hung on them were framed in a green about three shades darker than that. The pictures were guys in red coats on big horses that were just crazy to jump over high fences. There were two frameless mirrors tinted a slight but disgusting shade of rose pink. The magazines on the table of polished primavera were of the latest issue and each one was enclosed in a clear plastic cover. The fellow who decorated that room was not a man to let colors scare him. He probably wore a pimento shirt, mulberry slacks, zebra shoes, and vermilion drawers with his initials on them in a nice Mandarin orange.

 

I mean, your eyes hurt just reading that, right?

 

“The file you mention is top secret. In no circumstances must any confidential information be disclosed to outsiders. I’ll get it at once.” 

 

And this line, from a Jewish character:

 

“Well I ain’t a Christian, and I’m not knocking Christians, you understand. But with me it’s real. I don’t just say it. I do it.” 

 

She had that fine-drawn intense look that is sometimes neurotic, sometimes sex-hungry, and sometimes just the result of drastic dieting.

 

“He had a gun,” I said. “In Mexico that might be enough excuse for some jittery cop to pour lead into him. Plenty of American police have done their killings the same way - some of them through doors that didn’t open fast enough to suit them.” 

 

When he opened the door the buzz from the living room exploded into our faces. It seemed louder than before, if possible. About two drinks louder. 

 

“That’s the difference between crime and business. For business you gotta have capital. Sometimes I think it’s the only difference.”

 

“There ain’t no clean way to make a hundred million bucks. Maybe the head man thinks his hands are clean but somewhere along the line guys got pushed to the wall, nice little businesses got the ground cut from under them and had to sell out for nickels, decent people lost their jobs, stocks got rigged on the market, proxies got bought up like a pennyweight of old gold, and the five per centers and the big law firms got paid hundred-grand fees for beating some law the people wanted but the rich guys didn’t, on account of it cut into their profits. Big money and big power gets used wrong. It’s the system.” 

 

I have to mention a baseball reference. If you know, you know.

 

Back in my dog house on the sixth floor of the Cahuenga Building I went through my regular double play with the morning mail. Mail slot to desk to wastebasket, Tinker to Evers to Chance. 

 

And this bit from the cynical Marlowe to his cop friend:

 

“Sure, shut me up. I’m just a private citizen. Get off it, Bernie. We don’t have mobs and crime syndicates and goon squads because we have crooked politicians and their stooges in the City Hall and the legislatures. Crime isn’t a disease, it’s a symptom. Cops are like a doctor that gives you aspirin for a brain tumor, except that the cop would rather cure it with a blackjack. We’re a big rough rich wild people and crime is the price we pay for it, and organized crime is the price we pay for organization. We’ll have it with us a long time. Organized crime is just the dirty side of the sharp dollar.” 

 

There you go, a bit of the flavor of the book. Classic noir. 




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