The best books on hard-boiled PIs

Neal W. Fandek Author Of Peter Pike and the Lincoln Love Letters: (Ah, Love)
By Neal W. Fandek

The Books I Picked & Why

The Maltese Falcon

By Dashiell Hammett

Book cover of The Maltese Falcon

Why this book?

This might be the easiest No. 1 in the history of No. 1s. Falcon is the gold standard of hardboiled detective fiction, the blueprint mystery-PI writers have faithfully followed for damn near a century now. Falcon lets PI Sam Spade careen into the world, a new kind of tough-guy anti-hero hero, tight-lipped, wisecracking, violent, street-smart, with devastatingly sexy femme fatales, cheerfully amoral and very witty bad guys. The best part? Sure, the novel is better than the movie. It usually is. No, it’s the prose: Minimal, evocative, more so than even Hemingway. Hammett lets the story play out through the dialogue and action, not internal dialogue or literary devices, and still manages to create distinct characters. Spade’s lines can also be funny as hell, which Hemingway’s never were.


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The Dain Curse

By Dashiell Hammett

Book cover of The Dain Curse

Why this book?

What, more Hammett? Sure. My apologies to those expecting Raymond Chandler, but it’s hard to beat the master. Even in this sometimes almost incoherent thrill ride through the occult, drugs, the misdeeds of the rich, and amoral 1920s America. It ain’t called the Roaring 20s for nothing. This is the second in the Continental Op series and maybe Hammett’s most ambitious PI work, which follows a sharp-witted insurance investigator in Hammett’s trademark snappy prose. Sam Spade-like? Uh, no. The Op is short, fat, forty, and nameless, very far from a tough guy. He gets beaten up all the time in this, I admit it, quite convoluted novel. Fortunately for the mystery-challenged, the backstory is presented at the end of each of three parts, along with the Op’s wry takes on the case.

Is Curse a satire? A literary work? Some kind of skewed horror story? Yes to all the above.


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The Deep Blue Good-By

By John D. MacDonald

Book cover of The Deep Blue Good-By

Why this book?

The first novel in the 21-novel Travis McGee series introduces a kinder and gentler PI, a lazy beach bum who lives on a houseboat called the Busted Flush in Fort Lauderdale, Florida, and drives a Rolls Royce converted to a pickup (don’t ask me, I’m just the list writer). McGee is another knight errant with a strict moral code -- that excludes babes in bikinis, of course -- who's wary of credit cards, retirement benefits, political parties, mortgages, television. He only works when his cash runs out and his rule is simple: he'll help you find whatever was taken from you as long as he can keep half, in this case European gems smuggled in after World War II. The bad guy here is very bad indeed, a sadist who enjoys torturing women. McGee takes care of that, and recovers the loot, too, but both he and the client pay a heavy price.

This kind of morally ambiguous ending maybe didn't start with McDonald, but he perfected it and it’s now almost standard in PI fiction.


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Bright Orange for the Shroud

By John D. MacDonald

Book cover of Bright Orange for the Shroud

Why this book?

I could list almost any of the color-coded McGee series, but this one stands out: McGee helps an old buddy bankrupted by a real estate swindle. Vicious bad guys, rapists, killers, a tense stand-off and truly grisly ending for the bad guy -- yay! What makes this one special is Mac’s evocation of a rural Florida being devoured by greedy developers, a theme even more developed in Pale Gray for Guilt, 1968, where a buddy has been murdered because he refused to sell his waterfront property and … but that’s enough McDonald. If there is such a thing.


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The Murders in the Rue Morgue

By Edgar Allan Poe

Book cover of The Murders in the Rue Morgue

Why this book?

I know, this is a short story and hence cheating, but how can you make lists of detective stories without including the granddaddy of them all? Poe’s short story preceded Sir Arthur Conan Doyle’s Sherlock Holmes by four decades and has all the main ingredients. You have an ice-cold supremely rational detective, C. Auguste Dupin. You have a loyal sidekick. You have a bumbling cop. You have two extremely gory murders. You have a locked room. You have conflicting witnesses. You have a bizarre conclusion. You know what? Don’t read my No. 1. Read the Master first.


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