Why did Hollywood have such difficulty capturing Leonard’s appeal for so long? The adaptations of his early Westerns (3:10 to Yuma, The Tall T, Hombre) were largely successful, but after his switch to crime writing, the studios lost their knack for translating him to the screen. The failure was mostly tonal: Leonard’s work inhabits a unique point on the crime-fiction spectrum, neither as grimly hard-boiled as James Ellroy’s or Dennis Lehane’s on the one hand, nor as elaborately comic as Carl Hiaasen’s on the other. There is plenty of dry, ironic wit in Leonard’s work, but little in the way of jokiness.

Most of the early adaptations of Leonard’s crime work missed his light authorial touch, opting instead for somber noir. The 1969 version of The Big Bounce (starring a young but already wooden Ryan O’Neal) larded up a simple murder scheme with bleak subplots involving suicide and prostitution. Stick, a self-directed vanity project by Burt Reynolds, was all over the map tonally. (Leonard complained that “the plot was removed and machine guns substituted.”) And the director Abel Ferrara’s Cat Chaser—an initial, unreleased cut of which was three hours long and semipornographic—proved so traumatic an experience for the actress Kelly McGillis that she briefly quit acting altogether. Even relatively capable adaptations such as Mr. Majestyk (with Charles Bronson) and 52 Pick-Up (with Roy Scheider) emphasized the violence of Leonard’s books at the expense of character and dialogue.

It wasn’t until Quentin Tarantino arrived on the scene in the 1990s that an obvious cinematic vernacular for adapting Leonard presented itself. Though the two artists were separated in age by nearly 40 years, the affinities between them were evident: same ear for dialogue, same comfort with writing nonwhite and female characters, same don’t-take-it-all-too-seriously tone. (It should be noted, of course, that Tarantino’s work is far more violent than Leonard’s ever was.) Tarantino has frequently cited Leonard as a substantial influence on his writing. He was an ardent enough fan in his youth that when he was caught shoplifting a paperback of Leonard’s Switch at age 15, he later returned to the store, unchastened, to steal it a second time. When Leonard first saw True Romance (which Tarantino wrote but did not direct), he immediately recognized the congruity of their visions: “This is what one of my books should be,” he recalled thinking. Tarantino, as it turned out, felt exactly the same way. He later told Charlie Rose that he considered True Romance (which is set, in part, in Detroit) “basically like an Elmore Leonard movie that he didn’t write.”

Tarantino’s direct involvement with the production of Get Shorty, the first genuinely successful Leonard crime adaptation, was limited to his helping persuade John Travolta to take the lead role as Chili Palmer. But with Reservoir Dogs, True Romance, and Pulp Fiction, Tarantino had already offered a model for how to adapt Leonard to the big screen. (Leonard expressed his gratitude with a sly reference to Reservoir Dogs in his 1995 novel, Riding the Rap.) It was a model neatly adopted by Get Shorty’s director, Barry Sonnenfeld, and screenwriter, Scott Frank. For Frank, the primary challenge in constructing the script was to compress and offer structure while maintaining as much of Leonard’s dialogue as possible—because, as Frank noted, “The dialogue is what really drives the whole thing.” For Sonnenfeld, the trick was to allow Leonard’s native humor to come out naturally, without explicitly framing it as comedy. As Leonard recalled his own advice: “I told Barry, before he started shooting, ‘When someone delivers a funny line, I hope you don’t cut to another actor to get a reaction, like a grin or a laugh or something, because these people are serious.’ ”