Summary: A routine blackmail case opens a whole nother can of worms for Marlowe

If Rusty Regan had still been around General Sternwood would never have had to call Marlowe. But Rusty took off weeks ago and Sternwood needs someone discrete to handle this Geiger fellow’s blackmailing grift.

It seems like a straightforward gig to Marlowe. Then Geiger turns up dead. And everyone starts getting real interested in the whereabouts of former IRA commandant Terrance Regan.

Four things you can always count on Chandler for: twisty plots, strong atmosphere, femmes fatales, and prejudice. Just as I was feeling that The Big Sleep was remarkably free of the sort of bigotries that mar his other books, such as The Long Goodbye, Chandler decides The Big Sleep needs a discourse on gay men. Unsurprisingly Chandler’s thoughts on the subject are of the sort that probably render the reader just a little stupider in their reading.

There are bona fide loose ends in The Big Sleep: it’s never quite clear who killed everyone or why. But a thing that has always intrigued me about The Big Sleep is whether Chandler based the character of Regan on Ernie O’Malley.

Regan?

O’Malley, a former IRA commander and writer, spent a chunk of the late Twenties and Thirties in the US hanging out amidst artistic and literary circles. I can’t find any indication that Chandler and O’Malley ever met. But Chandler’s description of Regan does sound very like O’Malley: “a face that is sad rather than merry, more reserved than brash… a forehead broad rather than high, a mat of dark, clustering hair… the face of a man who would move fast and play for keeps.”

Admittedly this question is probably only of minority interest. What is more important is that if you can stomach Chandler’s horrible prejudices for a bit, this is a classic piece of hard-boiled detective fiction, beautifully written with moments of poetry, and gripping from start to finish.