The story's period was moved from 1949–50 to 1970s Hollywood. The Long Goodbye has been described as "a study of a moral and decent man cast adrift in a selfish, self-obsessed society where lives can be thrown away without a backward glance ... and any notions of friendship and loyalty are meaningless."
Late one night, with nothing better to do than feed his fussy cat, private investigator Philip Marlowe is visited by his close friend Terry Lennox, who asks for a lift from Los Angeles to the California–Mexico border at Tijuana. Marlowe obliges. On returning home, Marlowe is met by two police detectives, who accuse Lennox of having murdered his rich wife, Sylvia. Marlowe refuses to give them any information, so they arrest him. After three days in jail, the police release him, because Lennox committed suicide in Mexico. It is an open-and-shut case to the police and the press, but the official facts do not sit right with Marlowe.
Marlowe is hired by Eileen Wade, the platinum-blonde trophy wife of Roger Wade, an alcoholic novelist with writer's block, whose macho, Hemingway-like persona is proving self-destructive. She asks that Marlowe find her husband, who, despite regular alcoholic binges and days-long disappearances from their Malibu home, now seems to be missing. In the course of investigating Mrs. Wade's missing husband, Marlowe visits the subculture of private detoxification clinics for rich alcoholics and drug addicts. He locates and recovers Roger Wade and learns that the Wades knew the Lennoxes socially. He suspects that there is more to Terry's suicide and the murder of Sylvia. Marlowe incurs the wrath of gangster Marty Augustine, who wants money returned that Lennox owed him. Augustine maims his mistress just to demonstrate what could happen to Marlowe, saying, "That's someone I love. You, I don't even like."
After a side-trip to Mexico, where officials corroborate the details of Lennox's death, Marlowe returns to the Wades' house, where a party is broken up after an argument over Roger's unpaid bill from the detoxification clinic. Later that night, Eileen and Marlowe are interrupted when she sees a drunken Roger wandering into the sea; before they can stop him, he drowns. Eileen confesses that Roger had been having an affair with Sylvia and might have killed her. Marlowe tells this to the police, who remain satisfied that Roger's time at the clinic provides an alibi.
Marlowe visits Augustine, whose missing money has been returned. Marlowe then sees Eileen driving away. He returns to Mexico, where he bribes local officials into revealing the truth. They confess to having set up Terry's apparent suicide and admit he is alive and well in a Mexican villa. Marlowe finds Terry, who admits to killing Sylvia, reveals that he is having an affair with Eileen and gloats that Marlowe fell for his manipulations because Marlowe is "a born loser." Marlowe responds with "Yeah, I even lost my cat," shoots and kills Terry, then walks away, passing Eileen, who is on her way to meeting Terry. Marlowe pulls out his harmonica and strolls jauntily down the road, playing it.
The 1973 cinematic adaptation deviates drastically from the 1953 novel; screenwriter Leigh Brackett took many literary liberties with the story, plot and characters of The Long Goodbye in her adaptation. In a big plot and character departure from the end of the novel, Marlowe kills his best friend, Terry Lennox. The father of millionairess Sylvia Lennox is not in the film, Roger Wade's murder is a suicide in the film, and gangster Marty Augustine and his subplots are cinematic fabrications.
The Long Goodbye satirizes the changes in society between the 1950s, when the private-detective genre was popular, and the 1970s, when the film was released; a making-of featurette on the DVD is entitled "Rip van Marlowe" to emphasize the contrast between Marlowe's anachronistic 1950s behavior and the film's 1970s setting. One cliché of the genre invoked in the film is taken directly from the novel: when Marlowe, under police interrogation, asks, "Is this where I'm supposed to say, 'What's all this about?' and he says, 'Shut up! I ask the questions'?" Marlowe's chain smoking, contrasted with a health-conscious California, in which no one else smokes, is another example of his incongruity.
The American iconography that Chandler laid down in his novels is maintained in the film. In addition to the 1948 Lincoln Continental Convertible Cabriolet that Marlowe drives, Gould also wears a tie with American flags on it (the tie looks plain red in the movie due to cinematographer Vilmos Zsigmond's post-flashing).
Producers Jerry Bick and Elliott Kastner bought the cinematic rights to The Long Goodbye novel and made a production deal with the United Artists distribution company. They commissioned the screenplay from Leigh Brackett, who had been Kastner's client when he was an agent and had written the script for the Humphrey Bogart version of The Big Sleep. Brackett:
...set the deal with United Artists, and they had a commitment for a film with Elliott Gould, so either you take Elliott Gould or you don't make the film. Elliott Gould was not exactly my idea of Philip Marlowe, but anyway there we were. Also, as far as the story was concerned, time had gone by—it was twenty-odd years since the novel was written, and the private eye had become a cliché. It had become funny. You had to watch out what you were doing. If you had Humphrey Bogart at the same age that he was when he did The Big Sleep, he wouldn't do it the same way. Also, we were faced with a technical problem of this enormous book, which was the longest one Chandler ever wrote. It's tremendously involuted and convoluted. If you did it the way he wrote it, you would have a five-hour film.
Brackett says that Brian G. Hutton was originally attached as director and wanted the script structured so that "the heavy had planned the whole thing from the start" but when writing it she found the idea contrived.
The producers offered the script to both Howard Hawks and Peter Bogdanovich to direct it. Both refused the offer, but Bogdanovich recommended Robert Altman.
United Artists president David Picker may have picked Gould to play Marlowe as a ploy to get Altman to direct. At the time, Gould was in professional disfavor because of his rumored troubles on the set of A Glimpse of Tiger, in which he bickered with costar Kim Darby, fought with director Anthony Harvey, and acted erratically. Consequently, he had not worked in nearly two years; nevertheless, Altman convinced Bick that Gould suited the role. United Artists had Elliott Gould undergo the usual employment medical examination and a psychological examination attesting to his mental stability.
Jim Bouton, cast as Marlowe's friend Terry Lennox, was not an actor. He was a former Major League Baseball pitcher and the author of the bestselling book Ball Four.
In adapting Chandler's book, Leigh Brackett had problems with its plot, which she felt was "riddled with cliches", and faced the choice of making it a period piece or updating it. Altman received a copy of the script while shooting Images in Ireland. He liked the ending because it was so out of character for Marlowe. He agreed to direct but only if the ending was not changed.
Brackett recalled meeting Altman while doing Images. "We conferred about ten o'clock in the morning and yakked all day, and I went back to the hotel and typed all the notes and went back the next day. In a week we had it all worked out. He was a joy to work with. He had a very keen story mind."
Altman and Brackett spent a lot of time talking over the plot. Altman wanted Marlowe to be a loser. He even nicknamed Gould's character Rip Van Marlowe, as if he had been asleep for 20 years, had woken up, and was wandering around Los Angeles in the early 1970s but "trying to invoke the morals of a previous era". Her first draft was too long, and she shortened it, but the ending was inconclusive. She had Marlowe shooting Terry Lennox. Altman conceived of the film as a satire and made several changes to the script, like having Roger Wade commit suicide and having Marty Augustine smash a Coke bottle across his girlfriend's face. Altman said, "it was supposed to get the attention of the audience and remind them that, in spite of Marlowe, there is a real world out there, and it is a violent world".
Altman did not read all of Chandler's book and instead utilized Raymond Chandler Speaking, a collection of letters and essays. He gave copies of this book to the cast and crew, advising them to study the author's literary essays. The opening scene with Philip Marlowe and his cat came from a story a friend of Altman's told him about his cat only eating one type of cat food. Altman saw it as a comment on friendship. The director decided that the camera should never stop moving, and put it on a dolly. However, the camera movements would counter the actions of the characters so that the audience would feel like a voyeur. To compensate for the harsh light of Southern California, Altman gave the film a soft pastel look reminiscent of old postcards from the 1940s. When it came to the scenes between Philip Marlowe and Roger Wade, Altman had Elliott Gould and Sterling Hayden ad lib most of their dialogue because, according to the director, Hayden was drunk and stoned on marijuana most of the time. Altman had originally wanted Dan Blocker for the role of Wade but he died just before principal photography began. He was reportedly thrilled by Hayden's performance, despite him being second choice to Blocker. Altman's home in Malibu Colony was used as the location for the scenes that took place in Wade's house.
The soundtrack of The Long Goodbye features two songs, "Hooray for Hollywood" and the eponymous "The Long Goodbye", composed by John Williams and Johnny Mercer. It was Altman's idea to have every occurrence of the latter song arranged differently, from hippie chant to supermarket muzak to radio music, setting the mood for the hero's encounters with eccentric Californians, while pursuing his case.
Varese Sarabande released selections from Williams' score on a CD in 2004 paired with the album re-recording of Williams' music from Fitzwilly; in 2015 Quartet Records issued a CD entirely devoted to The Long Goodbye.
The Long Goodbye was previewed at the Tarrytown Conference Center in Tarrytown, New York. The gala was hosted by Judith Crist, then the film critic for New York magazine. The film was not well received by the audience, except for Nina van Pallandt's performance. Altman attended a question-and-answer session afterwards, where the mood was "vaguely hostile", reportedly leaving the director "depressed".
The Long Goodbye was not well received by critics during its limited release in Los Angeles, Chicago, Philadelphia and Miami. Time magazine's Jay Cocks wrote, "Altman's lazy, haphazard putdown is without affection or understanding, a nose-thumb not only at the idea of Philip Marlowe but at the genre that his tough-guy-soft-heart character epitomized. It is a curious spectacle to see Altman mocking a level of achievement to which, at his best, he could only aspire". The New York opening was canceled at the last minute after several advance screenings had already been held for the press. The film was abruptly withdrawn from release with rumors that it would be re-edited. Studio executives analyzed the reviews for six months, concluding that the reason for the film's failure was the misleading advertising campaign in which it had been promoted as a "detective story" and spent $40,000 on a new release campaign, which included a poster by Mad magazine artist Jack Davis.
The Long Goodbye was re-released and in his review for The New York Times, Vincent Canby wrote, "it's an original work, complex without being obscure, visually breathtaking without seeming to be inappropriately fancy". Roger Ebert gave the film three out of four stars and praised Elliott Gould's "good performance, particularly the virtuoso ten-minute stretch at the beginning of the movie when he goes out to buy food for his cat. Gould has enough of the paranoid in his acting style to really put over Altman's revised view of the private eye". Pauline Kael's lengthy review in the New Yorker ("Movieland–The Bums' Paradise", October 22, 1973) called the film "a high-flying rap on Chandler and the movies", hailed Gould's performance as "his best yet" and praised Altman for achieving "a self-mocking fairy-tale poetry".
Despite Kael's effusive endorsement and its influence among younger critics, The Long Goodbye remained unpopular and earned poorly in the rest of the United States. The New York Times listed it in its Ten Best List for film for that year, while Vilmos Zsigmond was awarded the National Society of Film Critics' prize for Best Cinematographer. Ebert later ranked it among his Great Movies collection and wrote, "Most of its effect comes from the way it pushes against the genre, and the way Altman undermines the premise of all private eye movies, which is that the hero can walk down mean streets, see clearly, and tell right from wrong".
In 2008, Empire magazine listed the film as one of the 500 greatest movies.