“Heavier than Broken Hearts”: Ranking the Raymond Chandler Novels


I did it. I finally read all seven Raymond Chandler novels and their companion short story collections. Chandler, while originating in pulp fiction, has come to be known as one of the great writers of the 20th century. Which begs the question: how do the adventures of the almost-noble, wisecracking detective Philip Marlowe stack up?


9. The Little Sister, 1949.

The Little Sister opens with Marlowe trying to swat a fly. Such an episode is so ridiculous as to make the novel parody, but The Little Sister is supposed to be dead serious. Known for labyrinthine plots, Chandler’s novels are often confusing, but The Little Sister is a narrative mess. The novel closes with three scenes featuring betrayals from not one, not two, but three femme fatales. That’s a bit much. The book’s one saving grace is a bizarre, self-reflective chapter in which Marlowe is in existential crisis. Something has changed. “You’re not human tonight, Marlowe.” The chapter foretells the narrative heights forthcoming in The Long Goodbye and to a lesser extent, Playback.


8. The Simple Art of Murder, 1950

The Simple Art of Murder is a story collection featuring an essay by the same name, in which Chandler distinguishes his and Dashiell Hammett’s genre from that of Agatha Christie and the like, and eight stories that don’t feature Marlowe but various similar gumshoes, mostly told from third person. The essay is outstanding, but the stories are a mixed bag. “Spanish Blood” and “Pearls are a Nuisance” are artistic, tragic standouts in a sea of forgettable episodes, though the plot device of a car with cyanide gas in “Nevada Gas” has been recycled in many TV shows.



7. The High Window, 1942.

The High Window delivers some classic scenes, but there’s a lot that goes unfulfilled in this one. Gangsters and henchmen are foreshadowed but don’t ever do much more than glare at Marlowe, and based on a pattern, it isn’t a true Marlowe story unless he’s hit over the head at some point. The book’s great strength is its self-aware attitude, in which there’s a scene where a villain basically says, “This is when you explain everything,” and Marlowe’s like, “You betcha.”


6. Playback, 1958.

Chandler’s last novel before his death is often criticized for being less complex than his others, but I think this makes it more like his long-form short stories in Trouble is My Business. Playback is good, thematically loyal and developing each character and using them as needed. True to the title, Marlowe is stuck in an infinite loop–he meets just about every character twice, he comes back to the same places again and again, and the heroine, like Marlowe, is haunted by her past. Playback also delivers something different from all the other novels: a happy ending.


5. Trouble is My Business, 1950.

Trouble is My Business features four killer Marlowe stories: the story of the same name, “Finger Man,” “Goldfish,” and “Red Wind.” These stories, as a whole, feel like a prequel to The Big Sleep. Marlowe is younger, more violent, and engaged in action and venomous comments at every turn. In “Finger Man” we meet Bernie Ohls, Marlowe’s one ally in the LAPD, for the first time, (who also appears in Big Sleep and Long Goodbye), and “Goldfish” is the definitive highlight here. An incredible collection.


4. The Lady in the Lake, 1943.

The Lady in the Lake probably earns the title of the “best of the rest” for being excellent but not particularly consequential to Marlowe’s storyline–kind of like a one-shot a la “Hound of the Baskervilles.” Featuring all the great hallmarks of Chandler: a labyrinthine (but plausible) plot, great characters, wicked comments, and rich locales. Traveling up to a lake resort town out of Los Angeles, The Lady in the Lake is one of the best.


3. The Long Goodbye, 1953.

The Long Goodbye is Chandler reaching for literary greatness. He doesn’t quite get there, but The Long Goodbye is a critical part of Marlowe’s canon. Marlowe is now wisened up and past his existential crisis in The Little Sister. Unlike the unsurity of “Trouble is My Business,” Marlowe knows what he’s all about. This is both a blessing and a curse. His new-found patience makes his character arc less interesting. The finale is suitably personal and quiet. The Long Goodbye says farewell to Chandler’s ally Bernie Ohls, his friend Terry Lennox, and the love of his life, Linda Loring. He only comes to grip with these losses in Playback.


2. The Big Sleep, 1939.

The Big Sleep is legendary for putting Marlowe on the map. The plot is well-organized, and the description is at times a bit sparse, but The Big Sleep is good, all right. The final speech that explains the title is incredible, and the somber, abrupt finish following the speech makes it a great work of fiction. But it still falls short of its immediate successor.RaymondChandler_FarewellMyLovely


1. Farewell, My Lovely, 1940.

I don’t know what it is about Farewell, My Lovely that puts it ahead of the others. Perhaps it’s the timeless adventure of Marlowe shaking off jewel thieves, a shocking encounter with a psychic, climbing aboard a gambling boat, or his trotting all around Los Angeles and Bay City, a euphemism for Santa Monica. Maybe it’s the fact that Marlowe, for the first time, finds a foil and romantic interest in Anne Riordan. But it’s also the tragedy that is paired with it. Farewell contains all the elements of a good Chandler novel, and combines them to great and wondrous effect. The best of all.

1 Comment

  1. This prompted me to peruse about half of The Drowning Pool – 133 pages or so – to see how many similes I could count. (I’m using the Vintage Crime Black Lizard edition from May 1996). I counted thirty four and no doubt missed a few. (REVISION, 11/21/14 – It is a much higher number. In my initial reading I was in a super noisy Starbucks on 39th and 8th and apparently this affected my concentration.) I haven’t done the legwork, but I think some of the later books might have a slightly higher ratio. That’s a lot, but in any case I would argue that many of Macdonald’s similes are so strong that they infinitely enrich the work. Not only that – they are so strong that they put many “serious” writers of fiction to shame.

    Liked by 1 person

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