Director Adrian Lyne was originally dismissive of casting Woody Harrelson as David, but changed his mind after watching White Men Can't Jump (1992). Harrelson said in one interview that doing love scenes with Demi Moore was uncomfortable because he was good friends with Moore's then-husband, Bruce Willis.

Director Adrian Lyne and Demi Moore often fought on-set over her character, with Woody Harrelson trying to be mediator between the two. Lyne had argued that he wanted Moore to show vulnerability, while the actress defended herself. It was later while Lyne was editing this movie that he realized she was portraying what he wanted all along, and he soon apologized to Moore.

Originally designed as a starring vehicle for Tom Cruise and Nicole Kidman, with Warren Beatty taking the part of the billionaire.

Demi Moore's black cut-out Thierry Mugler-designed dress generated such immense interest after the movie's release, it was often copied by other designers.

The tears shed by Demi Moore in the touching "girl that got away scene" in which Gage describes a past chance meeting with a beautiful girl are genuine. This scene was filmed without co-star Moore knowing any of Redfords dialogue, instead just being told to listen.

During the auction scene, John Gage (Robert Redford) is to leave the room. Redford kept missing his cue because he was listening to the jokes that auction emcee Sir Billy Connolly was saying.

John Gage's (Robert Redford's) tale of his encounter with an attractive woman on a New York City subway was taken nearly verbatim from a similar speech in Citizen Kane (1941).

The role of Diana was first offered to Julia Roberts, who turned it down.

On the DVD commentary, director Adrian Lyne says Robert Redford walks better than anybody on Earth and couldn't quite get over the fact he was working with him.

Halle Berry was interested in this movie, but was refused an opportunity to audition because the studio was afraid of adding an unnecessary racial undertone to the plot.

Diana is reading "The Firm" by John Grisham, which Paramount Pictures filmed soon after. The secretary at the real-estate office where she works is reading "Backlash", a book which criticized director Adrian Lyne for his portrayal of women in previous movies. Interestingly The Firm (1993) starred Tom Cruise, who had previously appeared with Demi Moore in A Few Good Men (1992).

Andie MacDowell was considered for the role of Diana Murphy.

Screenwriter Amy Holden Jones wanted Jason Alexander to be cast in the role of David and Diana's lawyer, but couldn't get Adrian Lyne to support the idea. Oliver Platt was cast in the role instead.

Woody Harrelson walked from Benny & Joon (1993), for which he had signed a contract, to do this movie. MGM sued, and Paramount Pictures settled for $500,000. Coincidentally, Benny & Joon's Johnny Depp had been approached to play David Murphy, which went to none other than Woody Harrelson.

John Cusack and Charlie Sheen turned down the role of David Murphy.

Porn star Randy West was Robert Redford's body double.

The movie was very loosely based on Jack Engelhard's novel. While it does contain the story idea of "a million dollars for one night with a man's wife", most of the book focused on Arab-Israeli intrigue.

Johnny Depp and Tim Robbins were approached to play the role of David Murphy. Had Robbins been cast in the role, he would have reunited with Adrian Lyne, his director of Jacob's Ladder (1990).

When this movie was first released on VHS in 1993, the first pressing cassettes were colored green. Paramount Home Video did this five times (five movies, five colors). The other four were The Hunt for Red October (1990) (red); Ghost (1990) (white); The Godfather: Part III (1990) (gold) and The Firm (1993) (blue).

The role of David was originally intended for Val Kilmer.

William Baldwin was considered for the role of David Murphy.

DIRECTOR TRADEMARK (Adrian Lyne): (lighting): Characters are often photographed with source light coming in from the side at eye level, which often causes them to be silhouetted.

In a 2020 interview, Demi Moore said when she read the script she was apprehensive about the amount of sex and nudity in the film even though she had posed nude for porn magazines before becoming an actress. So she cut a deal with the director saying he was free to shoot the scenes however he wanted, but she could review the footage and if there was anything she felt was too invasive or gratuitous, she would ask him to delete the clipping. But in the end she didn't find anything inappropriate about her scenes. She considered them to be more erotic than sleazy, which fit the tone of the film.

DIRECTOR TRADEMARK (Adrian Lyne): (water): When David (Woody Harrelson) finally confronts Diana (Demi Moore) about having sex with John (Robert Redford), Diana is washing dishes. Lyne often incorporates water with dramatic moments in his movies.

Michael Bay filmed the fast-tracking close-ups of the dice in the gambling scenes. He would then "remake" the same shots in "Armageddon".

This marks the second time that director Adrian Lyne and cinematographer Howard Atherton collaborated on a movie. The first being Fatal Attraction (1987).

Demi Moore finally got to work with Adrian Lyne on this movie after unsuccessful auditions for lead roles in Foxes (1980) and Flashdance (1983), which he also directed.

Sophie Marceau and Irene Jacob were auditioned for the role of Diana Murphy.

In the scene where David tries to reach for Diana at the roof top of the hotel, when the helicopter takes off, a big sign can be seen with the legend "LADY LUCK", which might be allusive to the situation taking place.

The car owned by David and Diana is a Citroen 2CV.

The film cast includes three Oscar winners: Robert Redford, Herbie Hancock and Billy Bob Thornton (coincidentally, all three won for work behind the cameras rather than for acting); and two Oscar nominees: Woody Harrelson and Seymour Cassel.

The last three letters on the license plate to David & Diane's car are "LYN". An obvious reference to director Adrian Lyne.

Woody Harrelson and Demi Moore appeared in Bunraku (2010).

Composer John Barry also worked with Robert Redford on Out of Africa (1985). Barry also worked with Demi Moore on The Scarlet Letter (1995).

Pamela Holt's debut.

Woody Harrelson dropped out of playing the brother in Benny and June when offered this film and was subsequently sued by MGM.