5 Oddball Detective Books That Are Made of Awesome

If you’ve been conscious at any time in the last century or so, you’re familiar with private detective tropes: the hardboiled operator who’s as quick with a biting quip as he is with a hand cannon, always getting mixed up with the wrong kind of girl as he doggedly follows the clues.
At least, that’s the typical detective. Over the years there have been some notable exceptions to this mold, detectives who are recognizably in a detective story but either don’t play the part at all, or find themselves involved in truly unusual mysteries. If you’re looking to mix up your detective story habit, here are five oddballs who will satisfy your yen for mystery and your yen for surprisingly creative worlds.
Inherent Vice, by Thomas Pynchon
Pynchon doesn’t really “do” plots, does he—at least not plots that make any sense in the conventional way. Which makes his decision to write a story structured similarly to a classic private eye story a fascinating one, but it works perfectly. Slacker/stoner detective Doc Sportello is an incredible entry in the category of literary detectives because he’s practically his own client: suffering from memory problems, apparent narcolepsy, and a myriad of other problems staying in sync with the real world, Sportello’s an unreliable narrator, seems aware of the fact, and isn’t troubled by it. While the central mystery is just a way for Pynchon to riff brilliantly for a few hundred pages, there’s a detective story at the core of this sprawling novel—one whose solution will surprise and challenge you. The book also serves as a lament of sorts for a moment in American history when it seemed like the Freaks were winning, which slots right in with the countercultural vibe of most detectives in modern literature.
Gun, with Occasional Music, by Jonathan Lethem
While most people seem to have forgotten or overlooked Lethem’s debut, it’s an absolute treat for anyone who loves a good detective novel and has a penchant for the absurd. In a sci-fi world where questions are considered rude and you can be punished for rudeness, how can a private detective work? The detective aspects of the story have a clear link back to Chandler, Hammett, and other classic detective novels, but the greatest trick Lethem has ever pulled (so far) is somehow making a kangaroo in a dinner jacket (an inspiration taken directly from a line in one of Chandler’s lesser works) feel completely organic to the story.
Dirk Gently’s Holistic Detective Agency, by Douglas Adams
While everyone remains aware of The Hitchhiker’s Guide to the Galaxy, Adams’ other major novels, the two Dirk Gently books, get much less attention. Which is a shame, as they are brilliant. Gently is a “holistic” detective who disdains merely solving one aspect of a crime. Since everything is connected, he seeks to solve the “whole” crime. Even better, Gently is a psychic who denies being psychic and claims to simply be very, very good at guessing. As with all Adams’ novels, the best bits are the throwaways—like a couch that gets stuck in a stairwell despite it being technically impossible for the couch to be stuck in that particular way according to the laws of physics—but what really makes the Gently books great is the fact that these classic Adams throwaway gags aren’t throwaways. They all circle back and tie together in insane but spectacular ways.
The Yiddish Policemen’s Union, by Michael Chabon
This fantastic novel is an alternative history novel, and what truly sets it apart from just about every novel ever written is how well it’s constructed. The alternative timeline, wherein Israel is destroyed in 1948 and a temporary Jewish settlement in Alaska becomes the Jewish state (something that almost happened) is simultaneously subtle and ambitious in scope. Add in a mystery that’s well-constructed just as a mystery, a long list of creative and fascinating characters (and genius riffs on one of the world’s most musical languages, Yiddish), and you’ve got a tremendous book that also happens to be an oddball detective novel.
The Robots of Dawn, by Isaac Asimov
The third book in Asimov’s Robot trilogy, Asimov explodes both science fiction and detective novel tropes in a story that combines domed cities, a human population struggling with an ingrained fear of outdoor space, robot technology, and space opera politics—and that doesn’t even touch on the actual mystery. What’s truly remarkable about the book (and the trilogy in general) is how Asimov makes the detective novel fit so well into the sci-fi novel, creating a rare breed: a mixed-genre book where almost no seams show. Also remarkable? Robots of Dawn was published 26 years after the second book in the trilogy, but you wouldn’t know it from the prose, which is as fresh and exciting as Asimov’s best.
What’s your favorite hardboiled (or not so hardboiled) detective story?