I spent my morning ("morning as in while I had breakfast, not morning as in the actual morning) dwelling on this, so I guess I might as well write something out. Caveats are as follows: I'm not a game designer, even as an amateur. I'm also not a film person. I'm a literature person. However, I'm specifically a genre critic, and one of my little side interests is hardboiled detective fiction. So, yeah, with all that said...
As Brock said, a lot of what we recognize as hardboiled is characters turning on the protagonist, debt, conspiracy, paranoia, and the protagonist getting the shit beaten out of them. Absolutely. We can sort of go back to first principles to see why that is.
Hardboiled detective fiction is, pretty obviously, a form of detective fiction. And detective fiction is a form of the gothic. If you haven't seen my "Gothic Library" series, I've nattered on at length about this previously, so sorry if you have seen it already. But basically, Poe invented detective fiction as we know it, centering on two dudes who live together, only wake up at night, cover their windows, burn candles, and decorate with skulls. One of these two is Dupin, the genius detective of two amazing stories and also a story that's awful. With that, and a few other stories like "The Gold Bug," Poe invented a genre within a genre. And Sherlock Holmes, by Doyle, took the football and ran with it. Wilkie Collins also wrote two excellent detective stories that are just gothic novels with detectives in. In The Moonstone the detective isn't even particularly good. He just talks about roses.
By the time we get to hardboiled fiction, Christie was already writing. So the market had what people now consider "typical" detective fiction, in which the novel has a "solution" and, to a greater or lesser degree, the reader should be able to figure it out.
Hardboiled detective fiction moves against that. You can't figure out the solution to a hardboiled mystery. Often, the detective can't figure it out. To some degree, that's not what they do.
Part of what really makes me love hardboiled fiction is this weird agency-within-powerlessness that the detectives have. They can't do anything. They usually aren't cops, they're not wealthy, they have no influence. If anyone knows them at all, they know them for having a bad reputation. But they're stubborn. So what happens, you see, is that they just keep going from place to place, asking questions, and riling up the perpetrators, until they commit one too many mistakes. The detective has to survive in the meantime, of course.
Most people think of Chandler's Marlowe when they think of hardboiled detectives, but my favorite hardboiled detective novel is actually Red Harvest, by Dashiell Hammett. Published in 1929, and coming from Hammett's earlier work in pulps, particularly Black Mask, this novel sets up a lot of what we think of as hardboiled, but it's still fucking weird.
Here's the beginning:
I first heard Personville called Poisonville by a red-haired mucker named Hickey Dewey in the Big Ship in Butte. He also called his shirt a shoit. I didn’t think anything of what he had done to the city’s name. Later I heard men who could manage their r’s give it the same pronunciation. I still didn’t see anything in it but the meaningless sort of humor that used to make richardsnary the thieves’ word for dictionary. A few years later I went to Personville and learned better.
Using one of the phones in the station, I called the Herald, asked for Donald Willsson, and told him I had arrived.
“Will you come out to my house at ten this evening?” He had a pleasantly crisp voice. “It’s 2101 Mountain Boulevard. Take a Broadway car, get off at Laurel Avenue, and walk two blocks west.”
I promised to do that. Then I rode up to the Great Western Hotel, dumped my bags, and went out to look at the city.
The city wasn’t pretty. Most of its builders had gone in for gaudiness. Maybe they had been successful at first. Since then the smelters whose brick stacks stuck up tall against a gloomy mountain to the south had yellow-smoked everything into uniform dinginess. The result was an ugly city of forty thousand people, set in an ugly notch between two ugly mountains that had been all dirtied up by mining. Spread over this was a grimy sky that looked as if it had come out of the smelters’ stacks.
The first policeman I saw needed a shave. The second had a couple of buttons off his shabby uniform. The third stood in the center of the city’s main intersection—Broadway and Union Street—directing traffic, with a cigar in one corner of his mouth. After that I stopped checking them up.
The style is of course what we tend to notice first; I can only speak for myself, but I think a lot of people have affection for that traditional hardboiled style, which a lot of people probably hear in the voice of Bogart. But look through just this handful of paragraphs and what you see is a decided class war brewing: the narrator gets his information from a mucker, which could be specifically descriptive as a laborer in construction, or more general as just a poor laborer, a regular guy. The cops are untrustworthy. But we notice that one of the biggest streets in the city is Union Avenue. That's not accidental. The entire novel is about union-busting.
As I'm now just talking about Red Harvest, it's worth noting that Hammett worked for the Pinkertons. The Pinkertons are best known now as strike busters. He quit, in fact, to focus on writing full time, because he was disgusted with the things he'd had to do on the job.
Here's some more of Red Harvest from later in the first chapter:
For forty years old Elihu Willsson—father of the man who had been killed this night—had owned Personville, heart, soul, skin and guts. He was president and majority stockholder of the Personville Mining Corporation, ditto of the First National Bank, owner of the Morning Herald and Evening Herald, the city’s only newspapers, and at least part owner of nearly every other enterprise of any importance. Along with these pieces of property he owned a United States senator, a couple of representatives, the governor, the mayor, and most of the state legislature. Elihu Willsson was Personville, and he was almost the whole state.
Back in the war days the I. W. W.—in full bloom then throughout the West—had lined up the Personville Mining Corporation’s help. The help hadn’t been exactly pampered. They used their new strength to demand the things they wanted. Old Elihu gave them what he had to give them, and bided his time.
In 1921 it came. Business was rotten. Old Elihu didn’t care whether he shut down for a while or not. He tore up the agreements he had made with his men and began kicking them back into their pre-war circumstances.
Of course the help yelled for help. Bill Quint was sent out from I. W. W. headquarters in Chicago to give them some action. He was against a strike, an open walk-out. He advised the old sabotage racket, staying on the job and gumming things up from the inside. But that wasn’t active enough for the Personville crew. They wanted to put themselves on the map, make labor history.
They struck.
The strike lasted eight months. Both sides bled plenty. The wobblies had to do their own bleeding. Old Elihu hired gunmen, strike-breakers, national guardsmen and even parts of the regular army, to do his. When the last skull had been cracked, the last rib kicked in, organized labor in Personville was a used firecracker.
But, said Bill Quint, old Elihu didn’t know his Italian history. He won the strike, but he lost his hold on the city and the state. To beat the miners he had to let his hired thugs run wild. When the fight was over he couldn’t get rid of them. He had given his city to them and he wasn’t strong enough to take it away from them. Personville looked good to them and they took it over. They had won his strike for him and they took the city for their spoils. He couldn’t openly break with them. They had too much on him. He was responsible for all they had done during the strike.
The professor with whom I first studied hardboiled fiction, in grad school, made a point once that we shouldn't be looking to Hemingway, Faulkner, or Fitzgerald to identify "the American voice" in literature. It's Hammett and Chandler. The style is directed at being both literary and of the people, from them. This is a real person talking about real shit, even if the narrator and the town don't exist.
I want to reel this back in to actually talk about ttrpgs soon, but the thing to keep in mind about this specific sub-genre is that it's typically underdogs because it's typically about poor people getting mixed up in rich people's bullshit. The cops don't care, because the rich people run their department, run city hall itself. The papers don't care, because their managers number among the rich. But what they do, like all gothic fiction, is peel back layer after layer, demonstrating that, well, the city is poisonville, after all.
The hardboiled novel I've read the most is, somehow, Chandler's The High Window. It's a Marlowe novel, but not one of the notable ones. The entire mystery is how a member of a rich family died by falling out of a window. And no one in the family wants Marlowe to investigate it -- they hire him, but then realize what it will mean to actually have the situation investigated. At one point they try to pay him to stop. He refuses. The narrator of Red Harvest is the same: he instigates a series of events that leads to multiple deaths, firefights, and the destruction of the city itself -- not in an apocalyptic fashion, I just mean a lot of property damage, death, and restructuring of the powers that be -- because he's too stubborn to stop what he's doing. No one wants him to figure things out. The father of the dead man tries to get him to leave. The wife of the dead man tries to stop him.
So that's where I wanted to get to. The thing about hardboiled fiction that's hardest to gather up in our hands, but most important to import into a ttrpg, is that sense of isolation and purpose. The PCs would, I think, need to be doggedly pursuing something that would, by virtue of their insistence, put them at odds with multiple groups.
Think of The Maltese Falcon. By the end, Spade is fighting with the cops, the criminals, and his own client. Everyone in the city seems to be against him, because everyone in the city seems to want the falcon (the premiere and original macguffin, after all). The internal motivations the PCs have for this doggedness will of course be their own. But no one is going to think they're a hero for this. Most people won't even know they exist. And everyone who does know, is going to want them dead.
Marlowe doesn't make friends with poor Black ushers and women of negotiable affection because he's a detecting genius who relies on information from the seedy side of town to make his cases. He does that because he's a poor alcoholic who's probably got ptsd and who can't make friends with anyone else. He's on the wrong side of the tracks, too.
We all love Columbo, but the comparable series, The Rockford Files, establishes immediately that Rockford is an ex-con who struggles to pay his bills, because it's overtly diving into the hardboiled tradition in ways that Columbo plays with instead.
So, how might you mimic this worldview mechanically and thematically in a ttrpg? Well, if you're designing it, you'd have to just say outright that it's going to be very rare for PC backgrounds to be cheery and full of friends -- at least, in the immediate past. I said I'm not a game designer, so I can't really imagine ways to do it mechanically. But your setting would be poor parts of town. GMs would be encouraged to describe bars, hostels, and the gutter in normal terms, but to describe police stations, the homes of the rich, and official offices in strange terms, making them alien spaces.
A thing to do with npcs is to remember that the PCs move through all the realms of good and bad, rich and poor, because they don't have a place of their own. The narrator of Red Harvest is randomly picked up by union men, union busters, moonshine runners, cops, and so on, both because he doesn't have the cultural cache to resist and also because he's a question mark, a person equally at home everywhere -- because he's at home nowhere.
That's what makes the hardboiled detective effective at detecting. They can go everywhere, because they're equally (un)comfortable everywhere.
In a few sentences in chapter three, the narrator of Red Harvest leaves the newspaper office, goes to the bank, then the police station, then the dead man's home, accompanied by the police chief. He doesn't go in disguise, or lie about anything -- though he can and will -- he just asks his questions, blows up any attempt to circumambulate out of embarrassment, and eventually people figure out he's asking questions, so they start meeting him.
So to revert to Brock's act structure, we might say a typical hardboiled narrative begins with the hook in act 1, and acts 1 through 2 are generally occupied by running around asking questions. Act 3 is where the fucking around stops and the finding out begins, with people converging on the PCs to ask just who the hell they are and just why the hell they're asking all these sensitive questions.
Act 4 would be where Brock's "rug pulls" happen, as everyone and their mother figures out that the PCs are either dangerous or poison. This would also be when one of the resources the PCs have is taken away, often by killing one of the few confidantes they had -- or making them turn on the PCs. And then act 5 is when they get enough information together to simultaneously show what happened and also why they shouldn't be killed.
They never get away with their wrangling. They just put everyone in a position from which it's better to let them go.
If you've been curious about why I have continually said "the narrator of Red Harvest instead of giving their name, you might be interested to know they aren't named. They're the narrator of three novels, in fact, and we never learn their name. People typically refer to them as "the Continental Op," as "Continental" is the name Hammett gave his fictional Pinkerton-likes.
