Cracking wise – the art of the hard-boiled sentence

Humphrey Bogart as Philip Marlowe with Lauren Bacall in The Big Sleep

Writing hard-boiled crime fiction isn’t as easy as it may seem. Although it appears to have a consistent structure, and a heavy emphasis on style, putting the elements together to create truly memorable lines takes skill. The prose of writers such as Dashiell Hammett and, my personal hero, Raymond Chandler, make it seem effortless but that’s because they worked hard to perfect their craft. Their cynical, world-weary private investigators, Sam Spade and Philip Marlowe, set the bar high when it comes to wise-cracking dialogue and vivid descriptions.

Here are a few examples:

Dashiell Hammett, The Maltese Falcon

“I distrust a man that says when. If he’s got to be careful not to drink too much it’s because he’s not to be trusted when he does.”

“Listen, Dundy, it’s been a long time since I burst into tears because a policeman didn’t like me.”

“My way of learning is to heave a wild and unpredictable monkey-wrench into the machinery.”

Dashiell Hammett, The Thin Man

“She grinned at me. ‘You got types?’
‘Only you darling – lanky brunettes with wicked jaws.”

“…I guess I can put two and two together.”
“Sometimes the answer’s four,” I said, “and sometimes it’s twenty-two…”

Raymond Chandler, The Big Sleep

“I don’t mind your showing me your legs. They’re very swell legs and it’s a pleasure to make their acquaintance. I don’t mind if you don’t like my manners. They’re pretty bad. I grieve over them during the long winter nights.”

“She lowered her lashes until they almost cuddled her cheeks and slowly raised them again, like a theatre curtain. I was to get to know that trick. That was supposed to make me roll over on my back with all four paws in the air.”

“Neither of the two people in the room paid any attention to the way I came in, although only one of them was dead.”

Raymond Chandler, Farewell My Lovely

“It was a blonde. A blonde to make a bishop kick a hole in a stained-glass window.”

“I needed a drink, I needed a lot of life insurance, I needed a vacation, I needed a home in the country. What I had was a coat, a hat and a gun. I put them on and went out of the room.”

Not only is it very difficult to write hard-boiled fiction well; it’s just as hard to write it in a deliberately bad way. That takes a certain skill too.

I’ve written before about the International Bulwer-Lytton Fiction Contest for bad opening lines. Every year writers are invited to submit entries for “the opening sentence to the worst of all possible novels” across a number of different genres, including crime/detective fiction.

The overall winner of the 2015 contest was Joel Phillips with this entry:

Seeing how the victim’s body, or what remained of it, was wedged between the grill of the Peterbilt 389 and the bumper of the 2008 Cadillac Escalade EXT, officer “Dirk” Dirksen wondered why reporters always used the phrase “sandwiched” to describe such a scene since there was nothing appetizing about it, but still, he thought, they might have a point because some of this would probably end up on the front of his shirt.

Some of the best entries (in my opinion)in the crime/detective category were given ‘dishonourable mentions’:

I knew that dame was damaged goods when she first sauntered in, and I don’t mean lightly scratched and dented goods that a reputable merchant like Home Depot might offer in a clearly marked end display sale; no, she was more like the kind of flashy trashy plastic knockoff that always carries a child-choking hazard that no self-respecting 11-year-old Chinese sweat shop kids would ever call theirs.  Tom Billings

The janitor’s body lay just inside the door, a small puncture wound below his right ear made with a long thin screwdriver, the kind electricians use and can often be found in the bargain bin at the hardware store and come with a pair of cheap wire cutters that you never use because they won’t cut wire worth a damn and at best will only put a small indent in the wire so you can at least bend it back and forth until it breaks.  E. David Moulton

And my personal favourite, especially with the clever nod to Chandler’s PI:

When private detective Flip Merlot spotted the statuesque brunette seated at the bar of his favorite watering hole, he was drawn to her like a yellow cat to navy blue pants, and when he sidled up next to her he felt fuzzy all over, kind of like dark blue corduroys get when they’re matted with yellow cat hair.  James M. Vanes

But let’s turn from the ridiculous to the sublime… here’s Humphrey Bogart and Lauren Bacall going head to head in The Big Sleep (1946):

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