15 Crime Novels as Funny as They Are Gritty

My love of both humor and illicit behavior started at a very young age, ignited by watching my two older brothers try to kill one another over the rights to whatever toy came in the box of Trix breakfast cereal my mother had just bought.

Silly rabbit, bloodlust is for kids.

As I grew up, I’d often find myself laughing in places that typically unsettle or disturb normal people. Places like hospitals, funerals, public school cafeterias.

After I learned to read… correction… after I learned to like to read—which didn’t happen until after college—I found myself drawn to books brimming with grit, grime, and crooked grins. I’d even laugh while reading dark fiction that wasn’t at all intended to be funny. For instance, I found Dostoyevsky’s Notes From Underground to be a riot, and I nearly peed my pants perusing Kafka’s The Trial.

Point is, there’s often a fine line between humorous and heinous, laughable and lurid, funny and frightening.

Following are 15 novels that will grip you with their grit while you bust a gut. Books that will have you laughing with and cheering on characters you’d probably be caught dead with in real life.

1) Swag by Elmore Leonard

There isn’t nearly enough room in this post to cite all the reasons why Swag tops this list. More to the point, I read it too long ago to remember exactly why it’s so damn good. Besides, Mr. Leonard—master minimalist that he was—wouldn’t have wanted me to go on and on about the book. Suffice it to say Swag’s one of the sharpest, grittiest, and funniest stories ever written about small-time criminals with big-time dreams, and there have been a LOT of those.

2) Bank Shot by Donald E. Westlake

I sometimes refer to Westlake as “Elmore Leonard Light.” This is not to infer the former is a lesser author than the latter; rather that Westlake’s crime capers are lighter on the grit and heavier on the humor. Bank Shot borders on madcap. It tells the tale of two hapless criminals who try to steal a bank. No, not rob a bank. Steal a whole bank. (Warning: Do not attempt to read any passages from this book while your mouth is full of food or drink.)

3) Claire DeWitt and the City of the Dead by Sara Gran

If you try to tell me Sara Gran is one of the most compelling female authors of crime fiction, I’ll take issue with you. Because she’s one of the most compelling authors—male or female—of any fiction. In this book (the first of the sensational series), Gran and her titular detective shake up PI clichés and tropes with sharp wit and plenty of pathos while taking the reader deep into the heart of post-Katrina New Orleans.

4) Skin Tight by Carl Hiaasen

One of the biggest compliments I’ve ever received as an author was from a reviewer who compared my work to that of Hiaasen. The reviewer was obviously drunk—and a close friend of mine who owed me money. No writer can out-funny or out-Florida the king of funny Floridian crime fiction. And Skin Tight (the first book in the Mick Stranahan series) is where Hiaasen’s satirical wizardry and love-hate relationship with the Sunshine State are on best display.

5) One For The Money by Janet Evanovich

I’ve never actually read this book, but was told I’d be an idiot not to include it in this list because the author herself would hunt me down (like the book’s bounty hunter protagonist would) and slap me for the snub. Based on the “Look Inside” excerpts I read on Amazon, One For The Money has a lot of good things going for it terms of New Jersey grit and grins. Hopefully, me saying so will be enough to keep me from needing a restraining order.

6) Kiss Me, Judas by Will Christopher Baer

I first read this darkly comedic cult classic years ago while on vacation in Tulum, Mexico. So don’t tell me a novel built around the urban legend of waking up in an icy bathtub with your kidney missing isn’t a beach read. It is. It was. I found the book to be so mesmerizing and edgy, I couldn’t put it down and thus forgot to get drunk on margaritas or try to have vacation sex with my wife. To this date, it’s her favorite book—and she’s never read a single page.

7) Beat the Reaper by Josh Bazell

I had never heard of this book or its author until a few years ago when a literary agent told me—in a rejection letter I’d received from her—“If you want to know what I’m looking for in terms of dark comedy, read Beat the Reaper by Josh Bazell.” In my defense, that agent can go to hell. Also, I’ll be forever grateful to her for the book recommendation. 

8) Filth by Irvine Welsh

Naturally, I had to include a novel by one of the godfathers of modern transgressive fiction on this list, and Trainspotting was just too obvious a choice. Besides, Filth is deserving of the spot. It’s as scathingly hilarious and as violent (and repulsive) as Welsh’s more famous novel. Plus, who doesn’t love a book where the character you’re expected to cheer for the most is a dirty cop who’s a horrible human being?

9) First Grave on the Right by Darynda Jones

You might think it’s strange to have a paranormal thriller on this list, but you’ll think differently after reading just a few pages of this book—the first in the renowned Charley Davidson series. With a protagonist who’s part private investigator and all Grim Reaper, Jones delivers a wickedly funny, wildly imaginative tale that will grip most mystery/thriller fans by the goodies and refuse to let go.

10) Gangsterland by Tod Goldberg

A novel about a hitman who hides from the mafia by becoming a rabbi following a botched hit is an intriguing premise. However I nearly left this book off the list—and for good reason: The author never followed me back on Twitter. But after reading it and laughing out loud while glued to my seat, I couldn’t deny Gangsterland deserved a spot. But if Goldberg doesn’t at least re-tweet my tweet about this article, I’m giving his spot to J.A. Konrath.

11) Remo Went Rogue by Mike McCrary

I met McCrary a couple of years ago at a “Noir at the Bar” event in Austin, before I’d ever read any of his work. The next day, eager to see if his fiction was half as cool as he was, I downloaded the Kindle version of Remo Went Rogue and dove in. The blazing narrative along with the witty, gritty, grimy dialogue grabbed me from the get-go and had me in stitches. I thought, “Is this guy this good, or am I still drunk from last night’s event?” After reading on, I realized both things were true.

12) Land of Shadows by Rachel Howzell Hall

Probably the most serious book on this list; nonetheless, it deserves a spot due to the quick wit and humor Howzell Hall manages to weave into her gripping, intense tale, which is set in racially explosive Los Angeles. As for grit, there’s no question. The plot and protagonist—homicide detective Elouise “Lou” Norton—are the very epitome of gritty in the city. Most readers will love how Detective Norton manages to keep her sense of humor in situations that are far from laughable.

13) Fight Club by Chuck Palahniuk

If you think I’m stupid enough to disobey the first rule of Fight Club, you are correct. I’m willing to be beaten to a pulp or murdered or worse to ensure that this daring and dangerously funny stick of literary dynamite gets included here. Some may say the book doesn’t really fit the “crime fiction” mold. That’s sort of the point. Also, c’mon—if trying to bring down the world’s financial system (and civilization as we know it) isn’t a crime, I don’t know what is. Except for not reading this book. 

14) Shooting Lessons by Lenny Kleinfeld

Mr. Kleinfeld is one of the most underrated and hilarious crime writers around, and Shooting Lessons—his latest novel—is arguably the best and definitely the boldest of his three novels. I mean, the guy fearlessly lampoons a fictionalized version of the NRA. Fans of Elmore Leonard and Carl Hiaasen will love Kleinfeld’s “gun-in-cheek” humor. And I’m not saying all these nice things about him or this book just because he followed me back on Twitter—he also “Liked” my Facebook page. 

15) Cherry by Nico Walker

You know when a friend tells you they just read a book that’s absolutely dazzling and dark and divine, and that you simply must read it, and then you do but it doesn’t live up to the hype? This isn’t that book. My friend actually didn’t hype the book enough. In Cherry, Walker—one of the most original voices I’ve read in years—tells a modern tale of war and heroin addiction that’s so visceral and heartbreaking, so humorous in the darkest way, you’ll forget it’s fiction. Which isn’t all that surprising considering the book is based largely on his life. What is surprising is the book—which debuted at number 14 on the New York Times bestseller list and was shortlisted for the 2019 Hemingway Foundation/PEN Award—was written inside a Kentucky prison where Walker’s currently serving the last year of an eleven-year sentence. I can’t wait for him to be released so he can sign my copy.

Your turn! What are some of the grittiest crime novels/thrillers that made you laugh? (And if you list one of MY novels, you’re likely my mother.)