The film had three weeks of rehearsals and was shot over 39 days. Most scenes were shot in single takes and then cut up in editing to try to replicate the theatrical flow and cadence of the dialogue. The film was also shot almost entirely in sequence.
David Mamet's screenplay considerably expanded his script for the play, providing more context for the pressure placed on the salesmen. Notably, Alec Baldwin's introductory speech was added as well as Jack Lemmon's phone calls to clients and the hospital, plus his sales call to the man with the fishing rod. Many consider the screenplay to be superior to the text for his Pultizer-winning stage play.
When approached about the movie, David Mamet asked for $500,000 for the movie rights and another $500,000 to write the screenplay, which Zupnik agreed to pay, planning to cut a deal with a cable company to bankroll the movie. However, because of the uncompromising subject matter and abrasive language, no major company was interested in financing the project. Ultimately, financing came from multiple small cable and video companies, a German television station, an Australian movie theater chain, several banks, and New Line Cinema.
David Mamet based his original play on his own time working in a real estate office in the 1970s when he was a struggling playwright. His job was the same as that of John Williamson (Kevin Spacey), the office manager who gave out the sales leads and handled the paperwork.
Alan Arkin turned down the film twice because he didn't like the character he was being offered; he thought Aaronow was an inherently unlikable and stupid character. However, upon reconsideration, Arkin created a backstory for Aaronow - he hadn't been a sales man very long, he was a teacher by trade, but the school in which he worked had got shut down, and he needed a job to support his family. Arkin says that he played Aaronow as an innocent rather that the usual stage depiction of him as a weak willed bumbler.
Alec Baldwin, was initially hired to play Blake (a role which wasn't in the original play), but with the agreement that if Al Pacino was unable to play Roma, Baldwin would play him. Early in preproduction it looked as if Pacino was going to be unavailable, so Baldwin began working on Roma, only for Pacino to join the project and Baldwin went back to Blake.
In the scene when Roma sits down at his desk to begin lying to James Lingk with Levine's help, he quickly takes his gum out of his mouth and tries to mash it under his desk. Al Pacino does this so quickly that the gum jumps from under the desk, across Pacino's/Roma's lap. In an example of great professionalism, Pacino keeps going with only a minor hesitation.
David Mamet's original play opened at the National Theatre of London in 1983 and then moved to Chicago before going on to Broadway, opening at the John Golden Theater in New York on 25 March, 1984 and running for 378 performances. The play won the 1984 Pulitzer Prize for Drama and was nominated for the 1984 Tony for Best Play, losing the latter award to Tom Stoppard's "The Real Thing."
A few little known facts about the filming location, at 1515 Sheepshead Bay Road NY, the building is owned by Premiere Properties (an existing, real estate company based in New York), who had its main office on the second story there, but had been moved to another location in 1991. Its vacant main office was then used for filming in 1992 without removing the lettering on the building and on the office door as an agreement to lower the rent of that office for filming purposes, in exchange for visibility of the company name. Also, the China Bowl Restaurant (which really existed back in 1992), on the opposite side of the street, is now a Chinese food store.
Originally, director Irvin Kershner wanted to turn the play into a film in 1985, and he persuaded his friend, producer Jerry Tokofsky, to read it. Tokofsky loved it, and contacted his associate Stanley R. Zupnik with a view to making a movie of the play with Kershner directing and Tokofsky and Zupnik producing. Kershner ultimately left the project in 1989 after becoming disillusioned with the lack of progress, but Tokofsky and Zupnik remained on-board.
The movie gained a newfound popularity in the punk community when Fat Mike of the band NOFX included the famous "the leads are weak" line at the beginning of the song "We Called it America", first track of the 2009 album "Coaster".
During the production, producers Jerry Tokofsky and Stanley R. Zupnik had a falling out over money and credit for the film. Tokofsky sued to strip Zupnik of his producer's credit and share of the producer's fee, but Zupnik filed a countersuit, claiming that he personally had put up $2 million of the film's budget, and accused Tokofsky of embezzlement. The cases were ultimately settled out of court with both men credited as producers.
The trivia items below may give away important plot points.
When one of the main characters is in a position of power, they chew gum (ex. Ricky (Al Pacino) when he's mocking Moss's (Ed Harris) attitude, Levene (Jack Lemmon) when he's insulting Williamson (Kevin Spacey) after Ricky is taken to the office, and Williamson when he's revealing to Levene that the Nyborg deal is no good).
During rehearsals, director James Foley would have the actors act out scenes that would happen off-camera; for example, he had Jack Lemmon and Ed Harris act a scene where Moss recruits Levene to rob the office, and Al Pacino and Jonathan Pryce act out the scene where Roma gets Lingk to invest in the land.
Although he's credited, Alec Baldwin only appears in one scene; where he's giving the speech where he breaks down A-B-C (which stands for Always Be Closing) and A-I-D-A (which stands for Attention, Interest, Decision, Action).