The best comic crime novels that inspired the best comic crime movies

Westlake was already a bestselling author of hard-boiled tales of a career criminal named Parker when he created that antihero’s lighter flip side, John Dortmunder, whose compatriots, capers, and consequences all come with some goofy, left-handed conceptual spin. The rock in the title is a famous African emerald, which Dortmunder and his mates set out to boost, only to find themselves having to steal the same gem a second time, and a third—eventually six heists, in all, from progressively impossible fortresses and in progressively outrageous ways. I’m inspired by the whole Dortmunder series’ blend of laugh-out-loud character pieces and genuinely inventive crime writing, and obviously I’m far from alone.

Like Dortmunder, Grimm is an idea man, and his idea for the perfect bank robbery is a doozy: he’ll dress as a clown, hold all the workers and customers in the vault, shoot out the video cameras, negotiate with the cops, take off the clown suit and makeup, “release” himself and his two accomplices as “hostages,” and waltz out of the bank and right past the entire NYPD. The only problem is, getting out of the city proves a lot harder than getting out of the bank. Cronley owes a lot to Westlake, but I picked Quick Change because he repays that debt and then some, with a smirking wit that lights up every page. 

Tolkin doesn’t hit you with belly laughs so much as tickle the upper corners of your mind with his knowing take on the mores and follies of the Hollywood of the late 1980s. (Of special interest to me, as that’s the moment I arrived there to begin my own TV and film career.) The trenchant satire is exemplified by the crime at its center: studio exec Griffin Mill, badgered by threats from some anonymous screenwriter he’s mistreated, focuses his attention on a different C-list scribe and winds up strangling him to death. Get it?  In a business full of writer-killing executives, Tolkin’s big-wig antihero literally kills a writer.

Most don’t think “comedy” when they think of Chandler, but I include his debut here to honor the sly wit behind the hard-boiled PI voice Chandler famously invented. Before him, nobody wrote sentences like, “Neither of the two people in the room paid any attention to the way I came in, although only one of them was dead,” but after him, every crime writer wanted a sprinkle of that. Of course, Chandler’s the all-time, undisputed champion of the simile, so adroit, so confident, that it’s okay if sometimes it feels like he’s playing beyond our grasp. “She was as sore as an alderman with the mumps”—what could that even mean? Beats me, but it’s enough to trust that Chandler knows, and somehow I’m smiling.  

Leonard’s the essential master of comedy-crime, full stop, so facile with the blend that he makes it look like he isn’t even trying. Here he conjures a charmingly impossible romance between gentleman bank robber Jack Foley and U.S. Marshal Karen Cisco, borne of an unplanned rideshare in a car trunk during a prison break gone sideways. Is this Leonard’s greatest novel, or does it just seem that way because it yielded far the best of his many adaptations? (Appropriate, by the way, for a book with the movies on its mind.) It’s no slight to director Steven Soderbergh or screenwriter Scott Frank to say that much of their magic was in knowing when to stay out of the maestro’s way.