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Artwork for Raymond Chandler, Part 5: The Long Goodbye
Book Report

Raymond Chandler, Part 5: The Long Goodbye

Chandler's last major novel, written beside his dying wife, about Marlowe's friendship with a charming drunk.

Friday, November 13, 2026 • 8:14 min

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The Long Goodbye is the longest and saddest of Raymond Chandler's novels, and the one he called his best book. He began it around 1949 at home in La Jolla, while his wife, Cissy, was in her late seventies and often bedridden with lung disease. He finished it as she was dying. It was published in Britain in November 1953 and in America the following March, and in 1955 it won the Edgar Award for best mystery novel. It is the closing part of this Book Report series.

The book opens with an act of kindness that Philip Marlowe cannot entirely explain. Outside a fashionable Hollywood nightclub, he sees a drunk young man in a Rolls-Royce. The man's hair is white, his face is scarred, and his manners are perfect. His name is Terry Lennox. His wife, a very rich woman named Sylvia, drives off and leaves him there. Marlowe takes him home and sobers him up, and a friendship begins.

It is an unusual friendship for Marlowe, who mostly keeps people at arm's length. The two meet in the late afternoons at a quiet bar called Victor's and drink gimlets. Terry explains the correct recipe: "a real gimlet is half gin and half Rose's lime juice and nothing else." Terry is a war veteran, divorced from Sylvia and then remarried to her, living on her father's money and openly ashamed of it. He is charming, weak and honest about being weak. Marlowe likes him.

Then, early one morning, Terry turns up at Marlowe's door with a gun and asks to be driven to Tijuana. Marlowe does it and asks no questions. When he gets back, he learns that Sylvia has been found beaten to death, and the police want to know where Terry went. Marlowe refuses to tell them. He spends several days in jail rather than talk. Then news arrives from a small town in Mexico: Terry Lennox has confessed in writing and shot himself. The case is closed, very fast, and people with money and power make it clear they want it to stay closed. Sylvia's father is a newspaper owner and one of the richest men in California.

A letter from Terry reaches Marlowe after the death. Inside is a five-thousand-dollar bill and a request: forget the whole thing, and drink a gimlet for him.

Marlowe does not forget it. The second half of the book appears to be about something else. A publisher hires him to find Roger Wade, a best-selling novelist who has gone missing on a drinking binge. Wade's wife, Eileen, is beautiful, composed and strangely remote. Marlowe finds Roger at a shady private clinic, brings him home, and is then asked to stay around and keep him sober long enough to finish his next book.

Roger Wade is the closest thing to a self-portrait Chandler ever wrote. Wade writes popular fiction that sells well, despises it, believes he could have been a serious writer, and drinks to get through the day. In one scene Marlowe finds a rambling, self-pitying confession Wade has typed while drunk. Chandler was writing about a successful author who drinks too much and thinks his work is beneath him, while he was a successful author who drank too much and suspected his work was taken less seriously than it deserved. Terry Lennox carries some of him too: the war, the English manners, the drink, the dependence on someone else's money.

The two plots turn out to be one. Without giving it all away, Roger Wade's household and Sylvia Lennox's murder are connected, and the connection runs back to wartime England. When Marlowe sees the whole pattern, he understands that the confession in Mexico was too convenient, and that he has been used by more than one person he trusted.

Chandler's agents did not like the first full draft. They felt Marlowe had gone soft, that he should be mocking his own sentiment instead of indulging it. Chandler revised, and broke with the agency. But the softness is what makes the book. Earlier Marlowe novels are about a man walking through corruption untouched. This one asks what happens when that man has a friend, and the friend is part of the corruption.

The book also slows down in a way the earlier ones do not. It is long, about one hundred twenty-five thousand words, and it spends time on things that have nothing to do with solving a crime: the rich in their gated valley, the economics of a famous writer's household, the loneliness of a man who comes home at night to an empty house. Marlowe is older now. He is still funny, but more of the jokes are aimed at himself.

There is a short love affair with Linda Loring, Sylvia's sister, who proposes marriage. Marlowe says no. She leaves, and he reflects on the French phrase that everyone quotes from this book: "To say goodbye is to die a little." He adds that the French have a phrase for everything, and they are always right.

The last chapter is a final meeting with someone Marlowe thought he had already said goodbye to. In it, he finally says what he thinks of Terry Lennox. Terry had standards, Marlowe tells him, but they were only personal, a matter of good manners and charm rather than anything he would pay a price for. He was as comfortable with crooks as with honest men, so long as they spoke decent English and had decent table manners. Marlowe gives back the five-thousand-dollar bill. The friendship is over. And the book ends with one of Chandler's driest lines: "I never saw any of them again, except the cops. No way has yet been invented to say goodbye to them."

The book had a long afterlife. Robert Altman filmed it in 1973 with Elliott Gould as a mumbling Marlowe in 1970s Los Angeles, a loose adaptation that has its own admirers. The novel itself is a good place to start for anyone who thinks they do not like detective fiction, because so little of it depends on detection.

Taken together, Chandler's books record one long argument. He believed that a crime story could be literature if it was honest about the world and the people in it. He wrote that the detective must go down mean streets without being mean himself. In The Big Sleep that man was a knight in a world with no use for knights. In Farewell, My Lovely he moved through a city where money decided which murders counted. In The Long Goodbye, written as Chandler was losing the person he loved most, the knight discovers that loyalty can be given to someone who does not deserve it, and that it can still be worth giving. That is a grown-up idea for a crime novel. Seventy years on, the slang has dated. What still holds readers is the man at the center: proud, broke, funny, and loyal past the point of good sense.

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