Over the holiday weekend I looked back briefly on the history of Labor in twentieth-century United States, and the bloody conflicts - including large-scale two-sided gun battles, one-sided massacres, lynchings and bombings – that it cannot be divorced from. Specifically, my mind snagged on the story of Appalachian coal.

Last week, I caught the new John Hillcoat film, Lawless – adapted from Matt Bondurant’s novel The Wettest County in the World – about a family of bootleggers in Virginia resisting the encroaching long-arm of the law - which, in this story, is depicted as little more than the extended will of ruthless men of means, pulling strings from Chicago to siphon the significant flow of money generated by the illegal, but popular, business into their own income stream.

And I was struck by the odd juxtaposition of the stories (the miners of Matewan and the bootleggers of Franklin), coming out of the same area in, roughly the same time. On the Labor side, the heroes are the poor and working class banding together to take up for each other and make a collective stand for dignity and humane conditions, while on the Bootlegger side, the heroes are the poor and working class refusing to be assimilated into a collective and taking a stance of fierce independence against any outside interest (a theme that also plays out in Westerns as well as tales of depression-era desperadoes like John Dillinger)…

I dunno… I thought it was interesting. Anyway, today I’m looking at some Bootleggers of crime fiction, that I've recently enjoyed meeting.

In Charles Frazier’s Nightwoods, Bud is a no-account small-time thief and a killer who sees a second chance at being a somebody when he beats a murder charge and inherits some property in short order. On that property is a honky-tonk that he takes over management of and builds on it a lucrative business with a network of stills and smuggler’s routes. But he’s not satisfied with that. At one point in the book, he even compares himself with Lucas Doolin, the back-road, hot-rodding, whiskey-running, Robert Mitchum character from Thunder Road, but it’s a different Mitchum film, Night of the Hunter (based on the novel by Davis Grubb) that the book more closely resembles, because he’s convinced that the children of the wife that he murdered know location of a secret stash of stolen cash his bride and victim hid from him, and he pursues them into the mountains with malevolent intent –

Which reminded of another novel owing much to Night of the Hunter, William Gay’s Twilight – now there’s a blackly-comic gothic yarn for your harvest season. But we’re looking at bootleggers now (not morticians), and perhaps my favorite of all is Dallas Harden from Gay’s debut novel The Long Home. He’s ruthless, cunning and entirely without fear or scruples, but he’s also one of the engaging, charismatic villains I’ve ever read – funny and wry on one page, scary as hell on the next – I couldn’t get enough of him.

The only repeat offender from the Labor list is Elmore Leonard with Son Martin from The Moonshine War. Son, the hero, has a stash of whiskey that he fears will be poached before he can sell it off. Set against him is another bootlegger and a bendable government agent. This one had a straight film adaptation in 1970, starring Alan Alda and Richard Widmark and Patrick McGoohan, but it's also the title chosen for the second season of Justified's first episode, and that one introduces bootlegger Maggs Bennet (in the role that would win Margo Martindale a much deserved Emmy), and Maggs straddles an important line in bootlegging mythology. While she keeps a still and is known for having the best shine around (which she sells from under the counter at her general store), she makes most of her money growing and distributing marijuana - which is more or less the current crime fiction equivalent of the prohibition-era bootlegger. 

So, this list could go into territory that would include Ben & Chon from Don Winslow's Savages or even Walter White from Breaking Bad (yeah, meth is perhaps an even better modern parallel - I guess any controlled substance that's home-grown and cultivated), but I'm not going there now. Can't wait for season three of Boardwalk Empire and the conclusion of Breaking Bad.

What about you? Who'd you put on this list? 

Jedidiah Ayres writes fiction and keeps the blog Hardboiled Wonderland.