The Edgar Awards Revisited: The Long Goodbye by Raymond Chandler (Best Novel; 1955)

We're revisiting every Edgar Award winner for Best Novel. Not every winner is well known, but that can't be said about 1955's winner, The Long Goodbye by Raymond Chandler.

Raymond Chandler. The name carries so much weight in the mystery genre, it’s hard to believe anyone who says they’ve never read any of his works. But I hadn’t. Like much of popular culture, after a certain time, the details are everywhere—reviewed, rebooted, interpreted, and imitated. I knew Philip Marlowe through and through without having read a single word. (Similarly, I hadn’t seen any of the Star Wars films until my 20s but could hold my own in any conversation about the films.)

It’s a shame that things get put on a pedestal like that because the expectations always overreach and cause an expectation for more. And that’s exactly what happened when I read Chandler’s The Long Goodbye (and watched the Star Wars films, for that matter).

Discover the first Edgar winner for Best Novel: Beat Not the Bones by Charlotte Jay!

Now, before you do a little PI work yourself and send some goons to help change my mind, chum, hear me out. The Long Goodbye was good. The dialogue was smart and quippy, the plot featured many excellent twists, and for all its genre trappings, it was quite literary. But because ya gotta read Chandler and Chandler is the best, I came away from it thinking it was just good, not great.

The Long Goodbye is Chandler’s sixth Marlowe novel. Originally published in 1953, it won the Edgar Award for Best Novel in 1955. The story begins outside a fancy club called The Dancers, where a chance encounter with a drunk man named Terry Lennox eventually gets Marlowe mixed up in a world of trouble—a world inhabited by the rich and ritzy of Los Angeles’ elite. Embarrassed by his drunken behavior, Lennox’s wife leaves him at the club, and Marlowe drives the man to his home until he can sober up.

The two strike up a sort of friendship—sharing a few early drinks at a quiet bar every now and then—until Lennox shows up at Marlowe’s house late one night asking him to drive him to Tijuana because he is in a great deal of trouble. Details can be implicating, so Marlowe agrees under the conditions that Lennox withhold all specifics of why he needs to escape.

Upon returning home, Marlowe learns that Lennox’s wife was found murdered in their guest house, and he’s arrested on suspicion of murder after refusing to answer the cops’ questions about Lennox’s whereabouts. He spends three days in jail before being released after it’s learned that Lennox was found in a small Mexican town and had committed suicide and left a full confession. Back at the office, Marlowe receives an odd letter from Lennox about his predicament along with a “portrait of Madison,” aka a rare $5,000 bill.

All’s well that ends well, right? Marlowe’s off the hook, and while it’s a shame his friend is dead, at least his involvement in that world died with him. But something about the details of the case doesn’t sit well with our seasoned detective—especially when he’s practically dragged into a seemingly unrelated job involving a famous alcoholic writer and his drop-dead gorgeous wife. The writer, Roger Wade, is known to get blackout drunk and disappear for a few days, but his wife is worried this time and enlists Marlowe’s help in finding him. Easy job, but once he’s returned the writer, he learns the couple knew Lennox, particularly Lennox’s murdered wife.

It’s here that the book gets a bit bloated. The central mystery involving the details of the Lennox case takes a lengthy backseat to Marlowe’s interactions with the Wades. While it’s ultimately an important relationship, the story drags along and seemingly ignores the Lennox case altogether for large chunks of pages.

However, this section is also where a big portion of the literary elements of the novel comes into play. Despite his contemporary success, Chandler was often hurt by critics’ reluctance to include him in literary discussions. In his introduction to Trouble Is My Business (1950), a collection of four of his short stories, Chandler touched on the dichotomy of critique in the genre:

As I look back on my stories it would be absurd if I did not wish they had been better. But if they had been much better they would not have been published. If the formula had been a little less rigid, more of the writing of that time might have survived. Some of us tried pretty hard to break out of the formula, but we usually got caught and sent back. To exceed the limits of a formula without destroying it is the dream of every magazine writer who is not a hopeless hack.

The Long Goodbye was clearly Chandler’s effort at breaking free of formula. It was his longest Marlowe novel by far, and it featured a good deal of social criticism about alcoholism, the wealthy, writing, and crime in general.

We don’t have mobs and crime syndicates and goon squads because we have crooked politicians and their stooges in the City Hall and the legislatures. Crime isn’t a disease, it’s a symptom. Cops are like a doctor that gives you aspirin for a brain tumor, except that the cop would rather cure it with a blackjack. We’re a big rough rich wild people and crime is the price we pay for it, and organized crime is the price we pay for organization. We’ll have it with us a long time. Organized crime is just the dirty side of the sharp dollar.

Around the time Chandler wrote The Long Goodbye, he seemed to be struggling pretty hard with life’s troubles. His wife, Cissy, was dying a slow death due to severe medical issues. He dealt with long bouts of melancholy where he found it difficult to write. He drank constantly. And it all showed in the book. The alcoholic writer who couldn’t seem to finish his book is most definitely Chandler’s way of inserting himself into the story—and likely working through some of his own issues with the help of Marlowe’s tough point of view.

Unfortunately, it’s during this portion of the book that the plot meanders and things sort of fall off the rails before the final denouement. However, it’s clear that Chandler was a master of dialogue and pioneer of hardboiled detective fiction. Now that I’ve read my first Chandler and my expectations have been tempered, I think I’ll go find out what all the fuss is about with Farewell, My Lovely.

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Some fun extra notes about The Long Goodbye

  • The novel has been adapted for television three separate times: 1954, with Dick Powell playing Marlowe (he also played Marlowe a decade before in Murder, My Sweet); 1978, with Ed Bishop as Marlowe; and 2011, with Toby Stevens playing the detective.
  • Robert Altman adapted The Long Goodbye for the big screen in 1973, with Elliott Gould as Marlowe. The film was quite a departure from the novel—taking several liberties in its retelling—and was not very well received. (You can read Thomas Pluck’s defense of the film here.)
  • Marlowe’s “picture of Madison” actually existed. High-denomination bills were last printed on December 27, 1945, and officially discontinued on July 14, 1969—though the $5,000 bill had largely disappeared long before then.
  • The published version is much different from the first draft. The agency who represented Chandler, Brandt and Brandt, felt Marlowe had grown too soft and would have seen through much of his actions exhibited throughout the novel. While Chandler ultimately agreed and rewrote much of the novel, including the ending—suggesting his mood and despair over his wife’s illness were likely to blame—the sentiment left him sour, and he dropped Brandt and Brandt before publication.

Notes on the 1955 Edgar Awards

  • The TV adaptation of The Long Goodbye was nominated for Best Episode in a TV Series but lost to “Smoke,” an episode from the series Suspense written by Gore Vidal.
  • Hitchcock’s classic Rear Window took home the Best Motion Picture award.
  • Dame Agatha Christie herself was the Grand Master. She also won the award for Best Play for Witness for the Prosecution.
  • Best First Novel was awarded to Jean Potts for Go, Lovely Rose.
  • Stanley Ellin, who you’ll read more about when we discuss the 1959 winner, won the Best Short Story award for “The House Party.”

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Thanks again for joining us as we work our way through this list. It is never easy following Raymond Chandler, but we have a feeling next year’s winner will be up for the challenge: Margaret Millar for Beast in View. Tune in Friday!

A special thanks goes out to The Mysterious Bookshop for donating many of the review copies of the award-winning books. For the latest on all new releases, as well as classic books for your collections, make sure to sign up for their newsletter.


  1. Kevin Burton Smith

    I don’t agree with all of your review, but it’s a fair one, and you present your case well enough, considering you’re judging the book through 2019 eyes. Which is, of course, the only way you can do it. What more could I ask?
    It’s your “fun extra notes” that need sprucing up.Toby Stephens and Ed Bishop both played Marlowe, alright, but on the radio, and the critical reception of Altman’s polarizing THE LONG GOODBYE has always been mixed, rather than totally negative. In fact, it’s become something of a cult favourite.

  2. Jimmy Raynor

    Chandler was well known for confusing and meandering plots, it was said when the “The Big Sleep” was being filmed he was called to help write the ending and he couldn’t explain it himself. But there is still great pleasure in i]his voice.

    • Barry Ergang

      Plotting wasn’t nearly as important to Chandler as character and style were. But unless my recollection is wrong, he wasn’t asked to script the ending of the Bogart/Bacall film. Bogart and Howard Hawks asked him to settle their bet about who killed Owen Taylor, and he told them he didn’t know.

      When I first read that in the collection of letters titled RAYMOND CHANDLER SPEAKING, it came as a great relief because, when I first read THE BIG SLEEP in my early teens, I went nuts repeatedly looking over the final chapters for the answer.

  3. Helen Martin

    After I read your article I re-read “The Long Goodbye”. Chandler does seem a bit down. I think he’s trying to work things that are bothering him. I also watched the movie again. It’s a startling departure from the novel. I’m a big Altman fans so I can’t be impartial. I hope you do read “Farewell My Lovely” I remember laughing at his comment on statue he comes across.

  4. Barry Ergang

    I first read THE LONG GOODBYE when I was in ninth grade, and found it rather disappointing because at the time I was into detective novels that were either traditional whodunits a la Christie and Gardner with lots of cerebration, or hardboiled fare a la Prather and Spillane with loads of action. But there was something about it I found appealing–Chandler’s style and Marlowe’s wry outlook–because eventually, after reading earlier Chandlers, which were more conventionally hardboiled, I read THE LONG GOODBYE again. I decided it was my favorite of his novels precisely because it departed from the genre’s conventions. I read it four more times over many years, and may yet read it again because it’s my all-time-favorite novel independent of genre. In case you’re interested, you can find my take on it here:

    I once read an article in which Robert Altman said he wanted to satirize the hardboiled private eye story and thus filmed “The Long Goodbye,” the script of which was written by Leigh Brackett who should have known better because the novel was NOT representative of the P.I. novels that had been written to that point. If he had to pick on Chandler, Altman should have used one of the earlier novels. “The Long Goodbye” is to Chandler as “Gosford Park” is to Christie–NOT!!

  5. Henry Kujawa

    Thanks to the Ed Bishop radio shows, I’ve finally experienced all of the Marlowe novels more-or-less in their original forms. Of them, “THE BIG SLEEP” is the most COHERENT. I suspect his short stories hang together better, judging by the Powers Booth TV adaptations. I can see why “FAREWELL MY LOVELY” inspired 3 very-different films, there’s too much junk in that single story and it needed stream-lining. Michael Winner’s film of “THE BIG SLEEP” remains my favorite because it’s NOT confusing if you just pay attention. And he very simply DID fix the one glaring plot hole. I saw it in a theatre and didn’t get lost once. Then I read the novel, and was amazed they were so close. Then I saw Bogart… and it took me 6 viewings for his film to make any sense at all. (heehee) I do love it, but for completely-different reasons, and tend to watch both films back-to-back.

    Dick Powell’s “THE LONG GOODBYE” was the pilot episode of “CLIMAX!”, and is sadly lost. “CLIMAX!” also adapted “CASINO ROYALE”, and believe it or not, by removing the 2nd half of the novel and allowing Bond to free himself and kill the baddie himself, I thought it IMPROVED on Fleming’s novel.

  6. 바카라사이트

    Another image, taken at a 1983 state dinner at the MH de Young Museum in San Francisco, shows Reagan laughing heartily at a joke told by the Queen.

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