It’s a toss-up between The Big Sleep and this book as to which is the best of Chandler’s Philip Marlowe novels. I lean toward The Long Goodbye. It’s the most coherent of the Marlowes and the most personal. Chandler’s trademark similes are a touch more nuanced here, and many of the themes are drawn from Chandler’s life.
Marlowe befriends Terry Lennox, a World War II vet who crawled into a bottle and hasn’t had a compelling reason to leave. He divorces and remarries a woman who seems more interested in bedding as many men as she can than building a life with Lennox. One day, Lennox asks Marlowe to drive him to Mexico, no questions asked. Marlowe knows something bad has happened but makes Lennox keep it to himself. It results in three days in jail for his trouble after Lennox’s wife turns up brutally murdered.
Not long afterward, Marlowe tries (and fails miserably) to turn down a job looking after alcoholic writer Roger Wade. Wade has a habit of blacking out and wandering off, often ending up at the ranch of a quack doctor who is happy to supply a “cure” for enough money. Eventually, the Wade’s domestic situation explodes in Marlowe’s face, and he finds himself disillusioned and disgusted. Normally, Marlowe lets his cases roll off of him. They change him, but in The Lady in the Lake and The Little Sister, he takes it in stride. As The Long Goodbye ends, he’s seriously considering packing it in and running off with an almost-divorcee.
Chandler wrote this during a period of deep depression. His wife was dying, and Chandler attempted suicide at least twice during this time. Lennox, Wade, and even police detective Bernie Ohls become surrogates for Chandler, which makes Marlowe something of a therapist for his creator. The result is a rather complex novel that runs much deeper than the earlier Marlowes. It’s too bad he died before finishing Poodle Springs. We’ll never know if he would have evolved parallel to Ross MacDonald.