Raymond Chandler is the quintessential American writer. Born in 1888, Chandler always loved writing, but failed to make an impression as a journalist. He abandoned any dream of the hobby when a fellow writer he considered more talented committed what Chandler called a “suicide of despair.” If a superior writer could lose heart, Chandler decided he had no chance, so he pursued a career in business, eventually becoming a high-paid executive for an oil company.
Chandler’s demons got the better of him, and at the age of 44 he was fired just as the Great Depression settled on the country. Desperate for money, he returned to writing and quickly became one of the greatest crime writers of all time—not to mention an inspiration to aspiring novelists everywhere because he didn’t publish his first novel until he was 51 years old. The 10 best Raymond Chandler books represent an essential reading list for anyone interested in detective fiction or the simple art of writing a killer line of prose.
Chandler’s debut novel The Big Sleep defined the noir detective genre and introduced Philip Marlowe, the detective who still serves as the iconic example for private investigator characters. Los Angeles is dark and gritty, filled with murderers and blackmailers, but Marlowe lives by a rigid moral code, and his hard-drinking, sarcastic presence masks a desire for justice and a rage for broken promises. The story is famously complex—or incoherent, if you’re being uncharitable (there are so many murders and double-crossings that one killing remains unsolved no matter how many times you read the book)—but the magic isn’t in the story of a wealthy old man seeking to snuff out a blackmail attempt on his wild daughter. It’s in the grim poetry of Chandler’s writing, which finds a dark beauty in the violent, loveless world Marlowe navigates. It was a revelation in 1939, and it’s a revelation to everyone who reads it now.
Chandler wrote his second-to-last completed work while dealing with his wife’s slow death, and The Long Goodbye combines the violence and grit of the classic noir detective story that Chandler perfected with a world-weary contemplation on loss and futility. Marlowe, steadier in purpose than he is in earlier stories, suffers in this one. He loses some of the most important people in his life, giving the book a Shakespearean quality.
The Long Goodbye is also a hilarious takedown of Hollywood and the vanity of the people who live and work there—and a vicious takedown of Chandler himself. Several characters in the story (most obviously the alcoholic, self-pitying author, Roger Wade) are stand-ins for Chandler, which makes the satirical bite immensely effective.
The eight short stories in this classic collection are solid pieces of short detective fiction. The stories predate Chandler’s seminal first novel, The Big Sleep, and chart a progression as Chandler evolves from being a good writer of noir detective fiction to becoming a master of the form.
Arguably more important than the stories themselves is the inclusion of the titular essay, originally published in The Atlantic Monthly in 1944. The essay is an amazing piece of literary criticism that states detective fiction belongs in any conversation about American literature, even though most of it is no good. Chandler’s ability to clearly set out what he thinks makes crime fiction special—and what makes it good—is remarkable, and anyone who reads or writes this genre will benefit from this short, punchy master class offered by one of its greatest writers.
Many rank Farewell, My Lovely as Chandler’s greatest novel due to the depth of the themes he explores. Published in 1940, the story opens with Chandler witnessing a murder. The victim is a Black man, so the Los Angeles police are less than interested in putting time and resources into solving the crime. Marlowe, a man of surprising justness despite his cynicism and tendency for violence, is outraged. Chandler wasn’t exactly a progressive firebrand, but his politics are clear and notable.
The novel’s origins as several short stories laced together (known as a “fix-up” novel) sometimes show their seams. The result is an overheated story that tries to mask its occasional lack of coherence with a breakneck pace — and it mostly works. As with many of Chandler’s novels, the story may not make perfect sense if you sit and think about it. The key is to immerse yourself in the tone poetry of the writing and revel in a story that introduced a basic template for noir fiction that is still followed today.
It’s true that two of the stories in this collection (Finger Man and Goldfish) also appear in The Simple Art of Murder, but the double-tap is worth it because of the other two stories (or novellas) included, the title story and the excellent Red Wind. Trouble is My Business is a classic example of noir’s enduring power as Marlowe is hired by a millionaire to run off a gold-digger who has her sights set on his son who soon turns up dead. Marlowe’s steady investigation and refusal to be seduced by anything or anyone leads him to a typically bleak solution to the murder, and the younger, more enraged version of Marlowe on display is a wonder to read.
Originally published in 1938, Red Wind is not only one of the most perfect noir titles ever conceived, it’s also unusual in that it takes place over just a few hours. Marlowe once again witnesses a murder, and in the course of investigating unspools a truly remarkable knot of blackmail, adultery, police corruption, and theft. The story represents the final crystallization of the character and techniques Chandler would employ in his longer work.
Chandler’s third Philip Marlowe book The High Window displays Chandler’s dim view of the wealthy and powerful coalesced into a defined theme that he explores with brutal gusto. The story is one of his twistiest, beginning with a deceptively simple case of a stolen, valuable coin and leading to multiple murders, blackmail, and a heap of manipulation perpetuated against a damaged, innocent woman.
The story sings despite the density and twists. Chandler’s dialog crackles, as does his description of a privileged world that Marlowe considers rotten. What’s truly remarkable about the story is that Marlowe solves the case, fitting every piece together perfectly, but doesn’t send anyone to jail. Instead, he follows his own idea of justice, finding human decency amidst the rot and ruin of Los Angeles and foregoing the typical solution. It remains a powerful way to end a mystery.
The Lady in the Lake displays Chandler operating at the height of his powers. The story is as twisty and grim as his first three Marlowe novels, and was partially fixed up from several short stories he’d written years before. Chandler’s firm control over his character and the world he inhabits allows him to introduce some increased complexity in the form of an elusive villain who appears frequently on the page, unrecognized until the reader reaches the end.
Chandler uses this to explore themes of perception and reality. Marlowe is a man who earns his living via the interpretation of clues, but Chandler demonstrates throughout the story that reality shifts every time we learn something new—and that we can be manipulated via the clues supplied. It’s a surprisingly deep noir detective story, and makes it one of the more successful of Chandler’s works.
Chandler spent much of the 1940s in Hollywood trying to make an impact as a screenwriter, but the experience yielded mixed results. Chandler had a low opinion of the film industry and the people who worked there. When he returned to novels, The Little Sister described Tinsel Town with the same acid and misanthropy he’d brought to Los Angeles. Many of the characters and events are taken directly from Chandler’s interactions in writers rooms and back lots.
The story is one of Chandler’s least coherent, rambling through a series of increasingly improbable murders, but the writing is sharp as ever. When viewed as a reflection of Chandler’s frustration in Hollywood, the story is more purposeful: The Philip Marlowe here is almost powerless, forever arriving too late to save people, and ultimately forced to step aside and let the police do their jobs if he’s to have any hope for justice.
Chandler’s last completed novel, Playback began life as a screenplay he tried to have produced while he was in Hollywood. He dusted it off years later and converted it into a novel, which may explain why it’s actually one of his most straightforward plots. When Marlowe is hired to find a woman named Betty Mayfield, he discovers that she apparently murdered her blackmailer. Marlowe follows the threads and the story and even gets something close to a happy ending.
Playback’s timeline is interesting and feints at a less miserable world, but at its core there is still the same moral authoritarianism. Philip Marlowe ultimately decides how things play out, who is punished and who walks free. That clarity makes this final effort by Chandler a remarkable cap to a remarkable series.
10. Poodle Springs
Unfinished at his death (he’d completed four chapters), Poodle Springs was eventually completed by Robert B. Parker and published in 1989. Parker did a fantastic job balancing his need to imitate Chandler’s style with modernizing the writing. He created a coherent and satisfying story, but the reason to read is those first four chapters that describe a whole new era for Marlowe. In those chapters, Marlowe is married to heiress Linda Loring (introduced in The Long Goodbye). Linda moves him to Palm Springs to live a life of idle wealth, which is just so… unexpected for a tough, cynical gumshoe like Marlowe. Parker turned this into an enjoyable Chandler pastiche, but the real fun is trying to spot invisible clues as to what Chandler was up to with this unexpectedly cheerful scenario. Chandler, a writer who saw poison in everyone and everything, might have had a lot of fun with Philip Marlowe making his way through high society as a member instead of an outsider.