The Big Sleep by Raymond Chandler
Why It's a Masterpiece (Week 67)

Raymond Chandler's The Big Sleep was published in 1939, marking his debut novel and the introduction of his private investigator, Philip Marlowe. Chandler had begun his literary career relatively late in life, writing upon his experience working as an oil executive and as a pulp magazine writer. His transition to fiction was spurred by the Great Depression, which led to his dismissal from the oil industry. A great blow to his income, but gave everyone else something to look forward to.
Before The Big Sleep, Chandler honed his craft by writing short stories for popular pulp magazines such as Black Mask. Many of the novel’s chapters are derived from these earlier works, a process Chandler referred to as "cannibalising." This method enabled Chandler to weave together a complex and compelling narrative that exemplified his style: atmospheric, cynical, and rich with sharp dialogue.
Published by Alfred A. Knopf, the novel was an immediate success and established Chandler as a key figure in crime fiction. The popularity of The Big Sleep was bolstered by its 1946 film adaptation, starring Humphrey Bogart and Lauren Bacall. If you haven't seen the film then you must get there immediately.
Plot

The novel opens with private investigator Philip Marlowe being summoned to the lavish Sternwood mansion. General Sternwood, an elderly and wealthy oil magnate, hires Marlowe to investigate a series of blackmail threats made against his wild younger daughter, Carmen. Sternwood also expresses concern about the disappearance of his former employee, Sean Regan, who had been close to both daughters.
As Marlowe begins his investigation, he quickly discovers that the Sternwood family is entangled in a web of deceit, criminality, and vice. The blackmailer, Arthur Geiger, operates an illicit pornography business. Marlowe tracks Geiger to his shop and later to his home, where he finds Geiger dead and Carmen drugged, seemingly having been photographed in a compromising situation. Marlowe destroys the evidence and escorts Carmen home, but the mystery deepens.
Marlowe investigates further and encounters Joe Brody, a petty criminal who had been attempting to exploit Geiger’s death for his own gain. Brody is subsequently killed by Carol Lundgren, Geiger’s lover, in an act of revenge. Despite this, the case remains unresolved, and Marlowe delves into the underworld of gambling and organised crime to uncover more truths.
Marlowe’s inquiries lead him to Eddie Mars, a shadowy and influential figure who is suspected of knowing the whereabouts of Sean Regan. Mars’s connections reveal layers of corruption and violence, including a staged disappearance and a deadly femme fatale in the form of his wife, Mona. Meanwhile, Carmen attempts to seduce Marlowe, who rebuffs her advances and begins to suspect her involvement in darker deeds.
The climax reveals that Sean Regan was murdered by Carmen after he rejected her. Vivian Sternwood, Carmen's elder sister, had covered up the crime to protect her family. Confronting Vivian, Marlowe insists that Carmen receive psychiatric help to prevent further harm. Though the immediate cases are closed, Marlowe is left with a lingering sense of disillusionment.
Into the Book

One of the central themes in The Big Sleep is the pervasive corruption that defines Los Angeles and the world of the novel. Chandler depicts a society where wealth and power protect the guilty, and morality is a luxury few can afford. The Sternwood family exemplifies this; despite their affluence, they are plagued by scandal, addiction, and criminality. Marlowe comments on this decay early in the novel, describing the Sternwood mansion as "impressive but rotten."
Marlowe himself is not immune to moral ambiguity. While he adheres to a personal code of honour, his methods are often unconventional and legally questionable. He is willing to destroy evidence and manipulate individuals to achieve a semblance of justice. This complexity makes Marlowe a quintessential anti-hero, embodying Chandler’s belief that in a corrupt world, conventional morality is insufficient.
“Dead men are heavier than broken hearts.”
- The Big Sleep by Raymond Chandler
Chandler’s portrayal of women in the novel is both fascinating and controversial. Female characters like Carmen and Vivian Sternwood wield significant power, often using their sexuality as a weapon. Carmen’s flirtation and eventual seduction attempts are key to the plot, but they also reveal her manipulative nature. When Marlowe resists her advances, he exposes the dangers of succumbing to such temptations in a morally compromised environment.
Vivian, in contrast, is more enigmatic. She is fiercely protective of her sister but also duplicitous, willing to cover up murder to maintain the family’s reputation. Her interactions with Marlowe are fraught with tension and mutual respect, showcasing Chandler’s nuanced exploration of gender dynamics. However, critics argue that the novel’s women are often reduced to stereotypes, reflecting the misogynistic attitudes of its time.
“As honest as you can expect a man to be in a world where its going out of style.”
- The Big Sleep by Raymond Chandler
Throughout the novel, Marlowe is depicted as a lone figure, operating on the fringes of society. His isolation is both a strength and a weakness, enabling him to navigate the city’s dark underbelly while remaining emotionally detached. Marlowe reflects on this alienation, noting, "I’m not part of their world, and I don’t want to be."
This theme is mirrored in the broader setting of Los Angeles, a city characterised by anonymity and disconnection. The sprawling metropolis serves as a metaphor for the fractured relationships and moral ambiguity of its inhabitants. Marlowe’s encounters with other characters often reinforce his role as an outsider, emphasising his alienation from the corrupt systems he navigates.
“He sounded like a man who had slept well and didn't owe too much money.”
- The Big Sleep by Raymond Chandler
Why It's a Masterpiece

The Big Sleep is seen as a masterpiece of crime fiction due to its narrative style, complex characters, and profound themes. Raymond Chandler’s prose is celebrated for its literary quality, combining vivid descriptions, sharp dialogue, and poetic metaphors. His ability to evoke atmosphere is unmatched, bringing to life a shadowy Los Angeles that feels both real and mythic.
Philip Marlowe is a revolutionary figure in detective fiction. Unlike earlier detectives, who often embodied moral perfection, Marlowe is deeply flawed and human. His wit, integrity, and vulnerability make him an enduring protagonist, redefining the genre’s expectations.
Chandler’s work transcends its genre, appealing not only to fans of detective fiction but also to literary scholars. His exploration of themes like corruption, gender, and isolation elevates The Big Sleep to a work of enduring significance, bridging the gap between popular and literary fiction.
Conclusion

Chandler’s prose, unforgettable characters, and exploration of themes resonate with modern readers is mind-blowing for the genre it is in. The portrayal of moral ambiguity, human frailty, and societal corruption is still a current topic; whilst Philip Marlowe’s wit and integrity continue to inspire writers today. As a great work of detective fiction, it paved the way for countless successors. In a world where justice often feels elusive, the novel offers both escapism and a sobering reflection of reality, showing us perhaps why we should pay attention to the law but also critique it when necessary.
Next Week: Doctor Zhivago by Boris Pasternak
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Comments (1)
Because of my seizures, I have forgotten big chunks of my most favorite books. And sadly, that's also true with movies. I love old movies. I still own damn near a thousand on DVDs. I love everything Humphrey Bogart. I've not read the book, but I was captivated by the movie. As always, Annie, your critiques are spot on. ⚡💙Bill⚡