# Researching the classic 'Hard Boiled PI' character...



## BlackDragon (May 10, 2019)

I recently started writing on a new book featuring, effectively, 'archetypical' versions of a number of classic characters from film and literature. The Mad Scientist, The Rebellious Princess, The Chosen One, The Kung-Fu Monk, etc. Inter-universe travel and stuff. Thing is, one of the characters I want to add is 'The Hard-Boiled PI'. You know the type, right? Humphrey Bogart, cigarettes and bourbon, trench-coat and fedora, has a weakness for dangerous dames with nice gams...

...but belatedly, it's occurred to me that I don't actually KNOW that particular archetype very well, beyond those broad strokes and well-worn cliches. It's just never really been my genre, I guess. But if I am to write a character who is the EPITOME of the classic Hard Boiled PI, I need to be more familiar with them! I've picked up The Maltese Falcon for starters - figure that'll be a good starting-point - but I think I'll need more than that. Can anyone recommend any books or movies featuring truly archetypical specimens for further research?


----------



## midnightpoet (May 10, 2019)

Anything by Dashell Hammett, Raymond Chandler, the "Black Mask" magazine of the early 20's.  Just google "hardboiled" in Google and you'll get a lot.  It started my out my love for detective novels (I've written 3, 3 more on hold).

Try the "thrilling detective" website


----------



## BlackDragon (May 21, 2019)

midnightpoet said:


> Anything by Dashell Hammett, Raymond Chandler, the "Black Mask" magazine of the early 20's.  Just google "hardboiled" in Google and you'll get a lot.



Yes... the 'a lot' bit is the problem. In this age of web-searches,  finding enough information is rarely the problem. Finding the _right_  information in the absolute deluge supplied to you is the hard bit.  Hence, what I'm hoping for is advice to narrow the field - preferably  down to the level of a specific book or movie that you feel encapsulates  the character of the archetypal hard-boiled detective. Perhaps you could name one or two particular favorites, if you are truly such a connoisseur of the genre?


----------



## ironpony (May 29, 2019)

Are you planning on setting the story in the 40s or 50s like those books and movies?


----------



## Ralph Rotten (May 29, 2019)

The thin man.
He's not hard boiled...but his liver is pickled.


----------



## BlackDragon (May 30, 2019)

ironpony said:


> Are you planning on setting the story in the 40s or 50s like those books and movies?



Not exactly! However, one of the main characters is a P.I. literally transposed directly from 1940's L.A. So I need to get his attitude, mode of speech and general character to fit that era.


----------



## Terry D (May 30, 2019)

No way to do it other than to read those types of stories. Another writer to read would be Micky Spillane.


----------



## Bard_Daniel (May 31, 2019)

I'd also recommend Dashell Hammett (Red Harvest specifically) and Raymond Chandler. They had it down to an art.


----------



## Ralph Rotten (Jun 1, 2019)

" literally transposed directly from 1940's L.A. "

Will he be played by Nicholas Cage?


----------



## BlackDragon (Jun 3, 2019)

Bard_Daniel said:


> I'd also recommend Dashell Hammett (Red Harvest specifically) and Raymond Chandler. They had it down to an art.



Red Harvest, you say? I'll look it up and give it a read! Thanks for the recommendation.



Ralph Rotten said:


> " literally transposed directly from 1940's L.A. "
> 
> Will he be played by Nicholas Cage?



Nah, I've got Humphrey Bogart in mind for the role.  Sure he's dead and all, but with the way CG's been developing lately, that just means he won't be able to negotiate his salary quite as sharply as he used to...


----------



## Ralph Rotten (Jun 4, 2019)

So it's Sam Spade to the rescue, eh?


----------



## BlackDragon (Jun 5, 2019)

Ralph Rotten said:


> So it's Sam Spade to the rescue, eh?



Exactly. I'm still trying to nail down a name that INVOKES him - and a few other such characters - without being TOO on-the-nose. What do you think of Jimmy 'Diamonds' Malone?


----------



## seigfried007 (Jul 9, 2019)

BlackDragon said:


> Exactly. I'm still trying to nail down a name that INVOKES him - and a few other such characters - without being TOO on-the-nose. What do you think of Jimmy 'Diamonds' Malone?



Diamonds makes him sound more like a stripper. Jimmy's okay, but I think James might work better. Sam Spade wasn't a "Sammy". Gangsters can get away with kiddie or otherwise ridiculous nicknames, but hard-boiled PIs should have a more serious grain. Two or three syllables seems to be the norm for such characters, between first and last names, from what I've seen so far. The names often have an assonance or consonance to them (makes 'em catchy). Definitely like "Malone" though.


----------



## BlackDragon (Jul 11, 2019)

seigfried007 said:


> Diamonds makes him sound more like a stripper. Jimmy's okay, but I think James might work better. Sam Spade wasn't a "Sammy". Gangsters can get away with kiddie or otherwise ridiculous nicknames, but hard-boiled PIs should have a more serious grain. Two or three syllables seems to be the norm for such characters, between first and last names, from what I've seen so far. The names often have an assonance or consonance to them (makes 'em catchy). Definitely like "Malone" though.



Hm! Now that you mention it, I suppose Diamonds isn't ideal. I was trying to reference Sam SPADE by invoking another playing-card suit, you know? And Diamonds still beat calling him 'The Club' or 'Heart'...  I figured that the in-story explanation for the nickname was that his first big case, which put him on the map and got his name out and about, involved recovering some very valuable stolen diamonds... but yeah, it's not great. As for 'Jimmy', you're actually pretty spot-on when you invoke gangsters - the idea _there_ is that he's half-Italian and grew up in a mob-run neighborhood. Knows a lot of wiseguys, knows how to walk the walk and talk the talk, and largely tries to do his work without disrespectin' the don.

So I think I'll stick with Jimmy as his 'regular' name, though of course it says 'James' on his office door. Not sure about his nickname, though, or even whether I should drop it entirely... >_> maybe I need to read some more detective-stories for inspiration!


----------



## seigfried007 (Jul 11, 2019)

Different people in different positions and relationships will likely have different nicknames for him.

You wanna channel gangster, Antoni "Tony" Malone would work great. Plus, he might go by "The Club" due to weapon of choice or managing a gentleman's club. 

Alternatively, you could always try Clovis Club. Dmitri "Dimmy" Diamond. Helge Hardt.


----------



## tzebley (Jul 13, 2019)

I would like to start off by saying that I like your idea of a "Hard Boiled PI" but there is an underlining issues that hasn't been addressed yet, and that is the training and experiences that a Private Investigator has. Not to mention the way a Private Investigator thinks and processes data and evidence gathered throughout an investigation. I worked for a year with the International Private Investigators Union and through that experience I can tell you that in order to understand what makes a Private Investigator "Hard Boiled" you really have to understand investigations and each of the characters backstory.  A few starting books I recommend for understanding Private Investigation techniques are:

I, Spy - How To Be Your Own Private Investigator by Daniel Ribacoff

and

Introduction To Conducting Private Investigations 2nd Edition by Philip A Becnel IV

The reason I bring this up is that your typical P.I. does not just start out as a P.I. The greater majority of them have a background in Law Enforcement and/or some form of Military experience. What we deem to be "hard boiled" is typically a result of having years of experience in dangerous situations, seeing the horrible aftermath of murders, suicides and other disturbing events. These events, whether gruesome or not, take their toll on any Investigator and also influences the way that the investigator conducts their investigation. These experiences have one of two impacts on the Investigator. It can either harden them and they push through continuing their career causing them to become "hard boiled" or they realize that it is to much and move on to a different area within their chosen career field. The reason I bring up the training of a P.I. is because the process of an investigation through a private source, i.e an independent investigator, and a Law Enforcement Detective is different in several aspects. I am in no way saying that there is not similarities. I am saying that there are a variety of investigators that work in different fields. Such as a Corporate Investigations, Fraud Investigations, and Law Enforcement Detectives. Each may go about their investigation in similar ways, but interact with clients, witnesses and gather evidence in different ways according to the Law, field of investigation, and authority that they have. The hardening, as we see it, is more likely to develop in the Arson Investigator and Law Enforcement Detective than in the Corporate Investigator.  

Sorry for the long winded response, but I believe that understanding investigation techniques, experiences, and the back stories of these characters is essential in understanding what makes an investigator "hard boiled".


----------



## BlackDragon (Jul 22, 2019)

Ah, now, this is very useful stuff! I was, indeed, aware that P.I.'s tended to have a background in law enforcement - if only because they almost inevitably have one or more 'friends on the force' - and I had plans to gradually explore how he wound up _leaving_ the police to become a private detective. But I hadn't really gone into that much detail yet. Thinking along those lines - about not just what a 'hard boiled detective' should ACT like, but what kind of events might serve to MAKE him hard-boiled - is a very good idea indeed... not to mention rather... inspirational.


----------



## JustRob (Jul 22, 2019)

I have no advice to give on this subject; quite the opposite in fact. I wrote my solitary novel as an extension of an earlier short story that centred on a private eye bemused by a very unusual experience. In the novel this character was only a minor one and his experience was just a small episode in a much broader story, but I made the mistake of using an adapted version of the original short story as the opening chapter. When I sent the first hundred pages of the draft to a professional service for assessment the reader there suggested that I drop the main story entirely and focus on writing about the exploits of the private eye because he saw them as having a fascinating potential. I replied that I wasn't capable of writing at length about a private eye and that I had to stick with my chosen story. To avoid other readers getting misled I relegated my private eye to a much later chapter to take him out of the limelight. So, right from the outset I decided that stories about private eyes were outside of the scope of my work.

One fact that I did find interesting was that in literature the private eye character is often used as a metaphor for the reader's own "private eye", which may explain why such stories can often be written in the first person. Developing this motif, the world weary private eye who has seen it all before, anticipates people's behaviour and is phased by nothing any more may actually be representative of the literature weary reader who has read it all before, anticipates story lines and is impressed by very little any more. Maybe that's why I prefer to write about mysteries that a private eye couldn't solve, which brings me right back to the bemused private eye in my original short story. Hard boiled private eyes are the critical readers of the book of life in my view.


----------



## seigfried007 (Jul 22, 2019)

JustRob said:


> I have no advice to give on this subject; quite the opposite in fact. I wrote my solitary novel as an extension of an earlier short story that centred on a private eye bemused by a very unusual experience. In the novel this character was only a minor one and his experience was just a small episode in a much broader story, but I made the mistake of using an adapted version of the original short story as the opening chapter. When I sent the first hundred pages of the draft to a professional service for assessment the reader there suggested that I drop the main story entirely and focus on writing about the exploits of the private eye because he saw them as having a fascinating potential. I replied that I wasn't capable of writing at length about a private eye and that I had to stick with my chosen story. To avoid other readers getting misled I relegated my private eye to a much later chapter to take him out of the limelight. So, right from the outset I decided that stories about private eyes were outside of the scope of my work.
> 
> One fact that I did find interesting was that in literature the private eye character is often used as a metaphor for the reader's own "private eye", which may explain why such stories can often be written in the first person. Developing this motif, the world weary private eye who has seen it all before, anticipates people's behaviour and is phased by nothing any more may actually be representative of the literature weary reader who has read it all before, anticipates story lines and is impressed by very little any more. Maybe that's why I prefer to write about mysteries that a private eye couldn't solve, which brings me right back to the bemused private eye in my original short story. Hard boiled private eyes are the critical readers of the book of life in my view.



I wrote a detective story once but haven't finished it. It's not long fiction though, but it's going to be just as long as it needs to be. Detective was the POV, and what I remember most about his writing style was how he would describe people. Everyone he met got a police description. 



> On 23 March 2043, employees at the downtown sewage treatment facility scooped a baby from the filth. White male, black hair, eyes fused shut, born approx. 25 weeks gestation, 1lb 7oz. From the heels, he measured 16in; from the tail, he measured 20.






> On 14 May 2049, I cruised through something of an artsy district, looking for the Holistic Spa on Light Street so I could buy a gift card for my wife’s birthday. Because parking in front of the spa was full, I turned on East Cross Street and parked in front of a bakery.
> 
> 
> As I was getting out of the car, a white male, 6’2”, 200lbs, with black hair and green eyes came out of the bakery, and I suddenly had a lead on a dead case. He was wearing a burgundy apron stamped in pink paint for Posey’s Bakery. He had the longest, furriest ears I had ever seen. They stuck off the sides of his head and looked like those of a wild African antelope, not a human at all. In his long, knobby fingers, he held a tray of diced pastries as he beamed like a small child. “Hello,” he said. “My name is Ira. Would you like a donut?”
> ...





> Rosey’s house lay nestled in a middleclass district like thousands of others, split ranch, five bedroom, two-and-a-half-bath, two-story, brick bottom, eggshell top with wide siding that went out of style thirty years ago, dark roof, attached two-car garage with living space above. The driveway was heavily cracked when I pulled into it at 8:30. The walkway was flanked by small bushes that remain red through the year; a sugar maple was still spinning whirlybirds in the middle of the front yard.
> 
> 
> When I knocked on the door, it wasn’t Rosie who answered but an adolescent female, 5’7”, 120lbs, long blond hair, blue eyes, bright smile. “Hi, I’m Filly. You must be Detective Black,” she said, extending a hand.



While he's working on this case, every single person he meets, every single place he goes--they all get this treatment. I don't describe characters like this, but in first-person as a detective, apparently, it works really well. Can't get away with it with any other POV, I don't think.


----------



## BlackDragon (Jul 23, 2019)

Ah, now, that - or a more broad version of it - is something I often enjoy playing around with in my own writing. Shifting perspective between different characters, and from first-person to an omniscient third-person narrator, to showcase the different ways people think and view the world - and how it often conflicts with objective reality, to the point where one must ask whether any such thing even really _exists_...

For example, a person may be described markedly different when writing from the perspective of someone who is in love with that person, as opposed to someone who actively dislikes the person - their eyes colored by their emotions. A detail-oriented, logical person will note minutia about their appearance, a fashionista will focus on their dress or accessories, while an empathic individual mostly ignores that in favor of describing their facial expression and body-language. The same character can play many different roles to different people...

...more to the point, it's an intriguing way to characterize a P.I. - certainly makes sense - though I don't think it fits with my particular P.I. I see him as less 'police procedural' and more 'a guy who knows what makes people tick - particularly the very _worst_ kind of people'. Though... hmm. Thinking of it that way, that really just shifts it a bit to the side. Not noting down their personal data, mentally or otherwise, but trying to 'read' everyone he meets to see what they're _really_ up to. Liar or honest? Victim or crook? Looking out for number one or genuinely altruistic? Hrm. Would take a bit of rewriting to make it work, but it might be worth the trouble.


----------



## seigfried007 (Jul 23, 2019)

BlackDragon said:


> Ah, now, that - or a more broad version of it - is something I often enjoy playing around with in my own writing. Shifting perspective between different characters, and from first-person to an omniscient third-person narrator, to showcase the different ways people think and view the world - and how it often conflicts with objective reality, to the point where one must ask whether any such thing even really _exists_...
> 
> For example, a person may be described markedly different when writing from the perspective of someone who is in love with that person, as opposed to someone who actively dislikes the person - their eyes colored by their emotions. A detail-oriented, logical person will note minutia about their appearance, a fashionista will focus on their dress or accessories, while an empathic individual mostly ignores that in favor of describing their facial expression and body-language. The same character can play many different roles to different people...
> 
> ...more to the point, it's an intriguing way to characterize a P.I. - certainly makes sense - though I don't think it fits with my particular P.I. I see him as less 'police procedural' and more 'a guy who knows what makes people tick - particularly the very _worst_ kind of people'. Though... hmm. Thinking of it that way, that really just shifts it a bit to the side. Not noting down their personal data, mentally or otherwise, but trying to 'read' everyone he meets to see what they're _really_ up to. Liar or honest? Victim or crook? Looking out for number one or genuinely altruistic? Hrm. Would take a bit of rewriting to make it work, but it might be worth the trouble.



Oh, he does body language and such too, but lots of people do _that_. You may want to look into how cops read body language. I was pretty fascinated by how my detective characterized people right off--makes setting the characters up really tidy though. I don't have to slip descriptions in like I do with other POVs.

For instance, if someone looks to their right when asked a question, they're more likely lying than if they look to the left. 

POVs were one of my favorite parts to a particular sci-fi novel series I wrote in the early 2000s (which has been mysteriously and sadly lost). There were 21 POV characters--and, _whoo boy_--some of these people saw each other in totally different lights. Most of them weren't human either, and so it got _fun_.


----------



## kilgore (Sep 4, 2019)

Chinatown features the greatest gumshoe I've seen in Jake.


----------

