A Brief Guide to Private Eye Novels

If classic private eye novels aren’t at the top of your reading list, I can’t really blame you. Written by dead white men in stylized prose that’s an acquired taste for many readers, they follow a set of conventions and stock characters which have been mocked by every formative influence of the current literary set, from Sesame Street to Garrison Keillor to Bill Watterson:

The best writers in the genre rose far above this level, producing real works of literature which combine serious themes and social commentary with page-turning plots. But these books are needles in a haystack — a haystack that’s about 20% solid-but-forgettable entertainment, and 80% hopelessly dated or just never very good to begin with. And the most dedicated fans aren’t always the best guides for new readers, because they’ve often developed a kitschy affection for a lot of the crap.

Fortunately, you’ve got me to help you out. If you have ten minutes, I’ll tell you everything you need to know about the genre and narrow it down to just six essential books to get you started.

The Beginning

Sherlock Holmes was a private detective, and Poe’s Dupin may have been the first, but the kind we’re talking about was created in short stories in American pulp magazines in the 1920s. Some of these early pulp writers were quite good, but the only great one was Dashiell Hammett, whose work forms the protoplasm of the entire private eye genre. I’ve written about Hammett and his influence before, and his five novels are essentially prototypes of the private eye from different angles. The first and most important is his “Continental Op” character, who already demonstrated the familiar matter-of-fact, cynical, first person narration style:

That was all I could shake the neighborhood down for. I went to the Montgomery Street offices of Spear, Camp and Duffy and asked for Eric Collinson.

He was young, blond, tall, broad, sunburned, and dressy, with the good-looking unintelligent face of one who would know everything about polo, or shooting, or flying, or something of that sort — maybe even two things of that sort — but not much about anything else. We sat on a fatted leather seat in the customers’ room, now, after market hours, empty except for a weedy boy juggling numbers on the board.

In an odd way, part of this character’s appeal was his lack of depth. He didn’t have Sherlock’s violin, cocaine, mysterious brother or any of the other details that rounded him out. The reader never learns much about him at all:

Hammett conveys everything in dramatic form, but even though he tells everything from the Op’s point of view, he has been selective about how much subjectivity he allows us to see. The Op is a sort of camera obscura; if he is fatigued by his journey, baffled by his reception, fearful of the speed of the car or the sudden scream, he does not say so. This was a style much admired by the French existentialists in the forties and fifties, who gave it a sort of philosophic interpretation; to them it was a ‘zero degree’ prose suggesting a mind living completely in the present, in touch with an imminent reality.

The cerebral French in those days had a tendency to romanticize the physical Americans, but there is some truth to what they believed. One of the deepest pleasures of reading Hammett may come from the illusion he creates of a mind which never seems alienated, uncertain or even seriously troubled. It isn’t a primitive consciousness because it registers things with a certain aesthetic grace; if the world it describes is violent, it responds to that violence by simply attending to the business at hand.

— James Naremore

Hammett’s next detective character was Sam Spade in The Maltese Falcon, who is almost as much of a cipher. Spade is often cited as the first major private eye, largely because of the second film adaptation with Humphrey Bogart, but in the book he’s still not fully fleshed out.

Farewell, My Lovely (1940)

After a little while I felt a little better, but very little. I needed a drink, I needed a lot of life insurance, I needed a vacation, I needed a home in the country. What I had was a coat, a hat and a gun. I put them on and went out of the room.

Raymond Chandler’s character Philip Marlowe was the definitive private eye, filling in the details and interior life that Spade lacked, and moving him from San Francisco to Los Angeles. Hundreds of subsequent private eye characters have been more or less the same guy as Marlowe. You probably know this guy somewhat even if you’ve never encountered any of them, just through cultural osmosis. He’s in his thirties, about six feet tall, with a face on the brutal side of handsome and a build on the thicker side of fit. He’s frequently a veteran and nearly always an ex-cop, cast off the force for some type of principled insubordination, but retaining a trusted friend or two on the inside who can get him out of trouble and trade information.

Sarcastic and provocative toward police captains and mob bosses alike. Compelling to women but generally unmoved by them, and probably divorced. A mild and functioning alcoholic, frequently needing a drink but never needing ten. Not overly educated, but a little more educated than people expect. Lives and works in a big city with a corrupt overclass and a seamy underbelly. Do I need to go on?

Chandler wrote six great Marlowe novels, beginning with The Big Sleep in 1939 and ending with The Long Goodbye in 1953, followed by one and a half bad ones that we won’t talk about. I think the critical consensus has been drifting toward The Long Goodbye as his masterpiece, but it’s not the right one to read first. Farewell, My Lovely is the definitive Marlowe story for me, with all the ingredients: a femme fatale, a blackmail plot, a shady psychic, an amateur sidekick and a bombshell ending.

The Taste of Ashes (1957)

I hung up fast, feeling the muscles around my mouth knot into a grin that was no grin at all but a symptom of the same tension that comes when you draw to an open-end straight and raise the opener blind.

Ten minutes. It shouldn’t take any more than that. In ten minutes you can buy a suit, change the water in the fish bowl, get a bill of divorcement, open a savings account. In ten minutes you could go down the hall and look in the mirror over the sink and watch your hair turn grey.

Howard Browne was the best of Chandler’s pure imitators. His Marlowe is named Paul Pine and works in Chicago instead of LA. He appeared in four novels, of which The Taste of Ashes is the last and most accomplished, with Pine investigating the death of another private eye. Browne didn’t push the genre forward like the other writers here, but this is probably my single favorite private eye novel.

The Underground Man (1971)

Her eyes closed, and opened again with a changed expression, of wary loss. She leaned on the watermarked wall. The night was running down like a transplanted heart.

Ross MacDonald began as another Chandler imitator in the ’40s, but he would come to add almost as much depth to the character as Chandler had added to Hammett’s detectives. He was Chandler’s equal as a prose stylist and a better writer in most other ways, particularly in terms of plotting:

The thing I really loved about what MacDonald did… was the untold part of the mystery story. Because every mystery novel has an entire unseen storyline, the one that goes on behind the scenes. While the detective is chasing one lead, the killer is off on some other path, leaving bodies for him to stumble over chapters later. That was like a puzzle the writer in me wanted to solve. I started making timelines to see where these plots overlapped, and started understanding why so many literary writers were also obsessed with mysteries.
— Ed Brubaker

MacDonald’s detective was named Lew Archer (he became Harper in two Paul Newman movies) and his cases, like some of Marlowe’s, tend to involve wealthy families in Southern California and the secrets that are tearing them apart. MacDonald was very interested in Freudian psychology and generational conflict, later in environmentalism and social inequality, and these elements give his stories a tragic, fatalist tone. The screenwriter William Goldman described a typical Archer case:

…perhaps a full generation before the present time of the novel, two people come together, neither of them lethal alone, but united, deadly. And they do something terrible. They murder or steal or assume different identities. Or all three. It is a wild compulsive drive that operates on them. Sometimes what they do they do for money or lust or power. But mostly they do it for love. And they get away with it. And everything is quiet. Until Archer comes. Usually he is hired for something standard: my wife has left me — find her; my husband has a mistress — tell me who; my Florentine box is gone — get it. So he begins and gradually, obliquely, the generation-old crime is scratched alive.

You can’t go wrong with any of the Archer books (there are about fifteen) but The Underground Man is a personal favorite, and one of his most powerful stories— a good example of how his later novels pushed further into social criticism without losing their edge.

The Beginning of the End

Donald Westlake was a successful writer in other crime genres who saw the writing on the wall for the private eye formula. As he put it in 1982:

The next to the last stage of the Western was the hermetically sealed story about gunfighters and ranchers and schoolmistresses, none of it reflecting any reality anywhere, some of it joky about its artificiality, like Vera Cruz. The last stage of the Western was Sergio Leone, the spaghetti Western, The Good, the Bad, and the Ugly, pictures made exclusively in close-up because a long shot would have shown the characters standing on a barren airless moon.

A while ago the Mystery Writers of America joined up with a couple of overseas organizations to have a big meeting in Stockholm. The writers come from every continent. Private eye novels are being written and published, and read, in Kenya and Zimbabwe, in Japan, in Russia. What are these books? What truth do they connect to? The brevity of the early Black Mask days is long gone. The relevance of those days is gone. The vitality of novelty is gone. The reflection of an underlying truth is gone. I’m not really sure what’s left.

I think Westlake was right that there wasn’t much left to do with the Marlowe/Archer character by 1982; you couldn’t push him any further than MacDonald did. There are surely still a few versions of him appearing in new novels every year, but I can’t imagine they’re changing the formula.

My last three recommendations, then, will be writers who were able to twist that character into someone new. And the first was Westlake himself.

Murder Among Children (1967)

He pulled again at his drink, said, “Of course, that’s all changed now. You know how it is, some people blossom no matter what, but some need success, money, some sort of external symbol of value to build their self-esteem. That was me, all right… Two years ago, Mitch, I wouldn’t have walked into a place like this in threads like these for all the tea in Berkeley. Now look at me.”

“Success does make a difference,” I agreed. I assumed it did, because I knew very well that failure did.

Beginning in 1966, Westlake wrote a series of novels about an ex-policeman in New York named Mitch Tobin. Unlike the standard private eye, who left the force because he wouldn’t participate in a cover-up or was just too stubborn to take orders, Tobin has left in disgrace, after getting his partner killed while having an affair with a criminal’s wife. And unlike most private eye series, this one has a longer plot arc across the five books; he starts out crippled by guilt and almost catatonically depressed, and is slowly lured out of his shell to help with one case after another. Each case plunges him into an unfamiliar segment of society that he struggles to understand, and in Murder Among Children, it’s the younger hippie generation.

Tobin is a private eye with all the breezy confidence stripped away, one who’s openly struggling to reconnect to his wife, son and former colleagues and piece his life back together, while unsure if it’s even worth the effort. He appraises himself with the same critical eye as the suspects and witnesses he talks to, and it makes for a very different and compelling kind of narrative.

The Last Good Kiss (1978)

“Let me tell you a story,” I said, which didn’t help his confusion. “When I was twelve, my daddy was working on a ranch down in Wyoming, west of a hole in the road called Chugwater, and I spent the summer up there with him — my momma and daddy didn’t live together, you see — and my daddy was crazy, had this notion, which he made up out of whole cloth, that he was part Indian. Hell, he took to wearing braids and living in a teepee and claiming he was a Kwahadi Comanche, and since I was his only son, I was too. And that summer I was twelve, he sent me on a vision quest. Three days and nights sitting under the empty sky, not moving, not eating or sleeping. And you know something? It worked.”

“I’m not sure I understand what you’re telling me,” he said seriously.

“Well, it’s like this,” I said. “I had a vision. And I’ve been having them ever since.”

James Crumley’s detectives live in Montana, where they spend their downtime consuming huge amounts of alcohol and drugs. Every one of their “cases” involves a long, violent, Hunter Thompson-esque road trip. They have a conscience, but it’s a lot less strict than Marlowe’s:

Some clients think private eyes have a code, something like never quit or seek justice whatever the cost or punish the guilty whoever they might be, but the code is probably more like never give the money back.

The Last Good Kiss is his most famous novel, and one of the best crime novels of any kind. Crumley is a funny writer, but one of his themes is also the decline of the heartland (as you can see from the poem where he got his title) and this elegiac background hum is an interesting extension of MacDonald’s fatalism.

Eight Million Ways to Die (1986)

He was visibly drunk now, but only if you knew where to look. The eyes had a glaze on them, and there was a matching glaze on his whole manner. He was holding up his end of a typical alcoholic conversation, wherein two drunks take polite turns talking aloud to their own selves.

Lawrence Block is the only living author on this list, and his last book about this detective, Matt Scudder, appeared in 2011. There was also a good movie a couple years ago with Liam Neeson.

Scudder is a successor to Mitch Tobin, haunted by his past and trying to put his life back together. He’s trying to quit drinking, and visiting AA meetings in most of the books, while “doing favors” for people as an unlicensed PI.

In addition to his alcoholism, which turns up the dial on one of the standard private eye traits to create a whole new character, Scudder’s cases have a cop show or thriller feel, a more modern vibe than the typical private eye stories — colorful informants, gruesome and realistic crimes, and a constant drumbeat of tension. Eight Million Ways to Die is a prime example, with Scudder trying to avenge a murdered prostitute.

What’s Next

At this point, I doubt whether anyone can do something original with the private eye archetype, unless they change him so much that you couldn’t even really call him a private eye. Jack Reacher and Lisbeth Salander seem like two recent series characters with strong private eye elements.

Broad narratives of cultural decline are generally not worth arguing about (the death of the novel, the death of rock music) but as Westlake pointed out above, particular niches or subgenres often do have an era of peak achievement that comes and goes, as writers learn how to fully exploit the form. And the private eye is probably not even the right vehicle for exploring the same themes in a contemporary setting. So I doubt we’ll see any new private eye novels on the level of any of the ones above. But hopefully they’re enough to keep you busy for a while.