Marlowe's drinking buddy Terry Lennox flees to Mexico, leaving behind a dead wife and a lot of questions. Marlowe attempts to answer the questions, even though nobody wants him to and despite news coming from Mexico that anything he finds will be too late to help Terry, who has committed suicide. He also takes on a case involving Roger Wade, a bestselling novelist with a drinking problem. Only at the end of the novel is Marlowe finally able to say a proper goodbye to the friend he's lost.
In 1954, the novel was adapted as an episode of the Genre Anthology series Climax!; Marlowe was played by Dick Powell, who had played Marlowe before in the film Murder, My Sweet. A film adaptation, also called The Long Goodbye,note was released in 1973.
- The first time I laid eyes on Terry Lennox he was drunk in a Rolls-Royce Silver Wraith outside the terrace of The Dancers. The parking lot attendant had brought the car out and he was still holding the door open because Terry Lennox's left foot was still dangling outside, as if he had forgotten he had one. He had a young-looking face but his hair was bone white. You could tell by his eyes that he was plastered to the hairline, but otherwise he looked like any other nice young guy in a dinner jacket who had been spending too much money in a joint that exists for that purpose and for no other.
This novel contains examples of:
- The Alcoholic: Roger Wade, and Terry Lennox. Both are, interestingly, based on aspects of Chandler himself. Marlowe himself would be considered an alcoholic by today's standards.
- Belligerent Sexual Tension: Marlowe and Linda Loring.
- Bluff the Impostor: When a woman is giving a confession that Marlowe doubts, she talks of dumping a man's body in a reservoir and Marlowe asks her how she got it over the fence. She blusters about adrenaline and then Marlowe reveals that there is no fence. After she breaks down he admits that he's never been there and really doesn't know about fence or no fence. He just thought she was lying.
- Chandler's Law: As usual when Chandler himself used it, done with a twist. The plot kicks off when a man comes through Marlowe's door holding a gun — but it's Lennox, who's come to him for help, and just happens to have the gun for self-protection.
- Deadpan Snarker: Marlowe.
- Death Faked for You: Terry Lennox's death wasn't a suicide — because he never died at all. His death was faked by a few gangster friends.
- Femme Fatale: Eileen Wade. Played with a twist — she at first appears to be a Damsel in Distress who needs protection from her husband. Marlowe doesn't totally buy it, but is attracted to her anyway. She turns out to be quite manipulative and has a dark past.
- Knight In Sour Armor: Marlowe. By this point in the series, he's positively acidic.
- Lemony Narrator: Marlowe both unconventionally describes people and isn't above Leaning on the Fourth Wall.
- MacGuffin: Terry Lennox leaves Marlowe with a $5,000 bill as payment for helping him get out of the country. Marlowe, believing he hasn't earned the sum of cash, spends the entire plot refusing to spend it. Its only significant uses are: to involve Marlowe in the second case; and so Marlowe can pay it back to Lennox, giving them an excuse to meet up again in the conclusion.
- Official Couple: Marlowe and Linda Loring. Chandler specifically created the character to be the perfect match for a man like Marlowe (a sort of "Princess In Sour Dress" to his Knight In Sour Armor). Appropriately enough, she's the first woman we ever "see" Marlowe in bed with.
- Private Detective: Marlowe.
- Private Eye Monologue
- Rich in Dollars, Poor in Sense: The first time Marlowe sees Lennox, Lennox is so plastered he could not get into a Rolls-Royce. The attendant at The Dancers is not impressed.At The Dancers they get the sort of people that disillusion you about what a lot of golfing money can do for the personality.
- Screw Politeness, I'm a Senior!: Harlan Potter.
- Run for the Border: Terry Lennox flees to Mexico, apparently to escape capture for a crime he's committed. Marlowe doesn't quite buy it.
- Self-Deprecation: Terry Lennox and Roger Wade are both based on different elements of Chandler's own life and personality. Neither is depicted as a particularly admirable person.
- Spirited Young Lady: Linda Loring is a refined, dignified heiress who matches Marlowe's snark with some of her own, shares his Knight In Sour Armor approach to the world, and helps him a little in the investigation.
- The Stoic: Though Marlowe does have his more human moments, these mainly occur when he's been truly pushed over the edge. The rest of the time, though, he manages to remain completely deadpan even as he's being beaten up by crooked cops or having guns waved in his face.
- Talks Like a Simile: A feature of Marlowe's narration.
- Tap on the Head: Happens quite often.
- This Is the Part Where...: When Marlowe is first questioned by Sergeant Green and Detective Dayton, he says "This is where I say, 'What's this all about?' and you say, 'We ask the questions.'"
- Zillion-Dollar Bill: Marlowe receives a "portrait of Madison" (a $5,000 bill) for doing a small favor at the start of the novel. The bill causes no end of trouble.
- He turned and walked across the floor and out. I watched the door close. I listened to his steps going away down the imitation marble corridor. After a while they got faint, then they got silent. I kept on listening anyway. What for? Did I want him to stop suddenly and turn and come back and talk me out of the way I felt? Well, he didn't. That was the last I saw of him.I never saw any of them again-except the cops. No way has yet been invented to say goodbye to them.