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The working titles of this film were Thomas Crown, Esquire, The Crown Caper and Thomas Crown and Company. The film's opening credits show brightly colored photographs of the actors in shots from the picture, sometimes in small frames within the larger screen, and sometimes with only parts of their faces shown, with the facial features being mixed with others as they appear. The names of Steve McQueen, Faye Dunaway, Paul Burke and Jack Weston appear with their photographs. Although the picture's copyright claimant was Mirisch-Simkoe-Solar Productions, the actual production companies were The Mirisch Corporation, Simkoe and Solar Productions, Inc., the latter of which was formed by McQueen in 1961.
The Thomas Crown Affair marked the first feature film written by Alan R. Trustman, a Boston lawyer and former banker. According to contemporary sources, Trustman first thought of the film's story while working at a bank, and later wrote the treatment after becoming a lawyer. He sold the treatment to the William Morris Agency, which then interested director Norman Jewison. In modern sources, Jewison has noted that he worked extensively with Trustman on the screenplay.
In his autobiography, Jewison stated that both he and Trustman originally wanted Sean Connery for the part of "Thomas Crown," but Connery, tired after completing You Only Live Twice (see below), declined. Modern sources assert that Jewison also considered Rock Hudson for the role. McQueen, whom Jewison had directed in 1965's The Cincinnati Kid, lobbied hard for the part, which Jewison was reluctant to give him, as he felt it was too divergent from McQueen's onscreen and offscreen personas. Jewison also noted that among the many actresses considered to play "Vicki Anderson" were Brigitte Bardot, Julie Christie, Leslie Caron, Vanessa Redgrave, Sharon Tate, Raquel Welch, Candice Bergen and Anouk Aime. On the suggestion of McQueen, Jewison tested Camilla Sparv, but ultimately the part went to Dunaway on the strength of footage Jewison saw from 1967's Bonnie and Clyde before its release. Modern sources include Bruce Glover in the cast. The picture marked the screen debut of fashion model Astrid Heeren, although she went on to make only two more films.
As noted by contemporary sources, The Thomas Crown Affair was shot mostly on location in Boston, MA, with interiors filmed at the Samuel Goldwyn Studios in Hollywood. Studio publicity related that the production shot for ten weeks in ninety locations around Boston. In press releases, Jewison asserted that the initial bank robbery was filmed at the downtown branch of the National Shawmut Bank, and that although the guards and bank officials knew what was going on, the customers did not because the filmmakers were using a concealed camera. Although they apparently thought that a real robbery was occurring, none of the customers or pedestrians interfered in any way. In an October 1968 American Cinematographer article, director of photography Haskell Wexler clarified that it was mostly the exterior sequences that were shot at the Boston bank, with many of the interiors shot at the Goldwyn Studios. Hidden cameras were used frequently to photograph various street scenes in Boston as well. Other Boston locations listed by studio press releases include Beacon Hill, Copp's Hill Cemetery, the Commons and Crane's Beach, as well as Provincetown on Cape Cod. The glider scenes were shot in Salem, NH, according to contemporary sources. In November 2003, WSJ reported that the house used for Crown's mansion was a property on Beacon Hill that was one of three built by merchant Harrison Gray Otis.
According to modern sources, the producers applied to the FBI for cooperation in shooting the picture and sought to film the FBI headquarters in Boston, but the agency refused, claiming that the script made it look incompetent. Studio press releases noted that the dune buggy in the film was designed and customized by McQueen and Pete Condos, "an off-road vehicle builder." McQueen, a sports enthusiast, learned to play polo for the film and was taught by Gary Wooten and Neil R. Ayer, real-life polo players, as well as by first assistant director Jack N. Reddish, who was a nationally ranked player at the time. In February 1968, Box Office reported that United Artists had alerted distributors that the company would be seeking blind bids for exhibition rights to the picture, as prints of it would not be finished in time to be viewed before its release. Blind bidding was no longer a common practice by the late 1960s, and UA had to make special efforts to notify the National Association of Theatre Owners of its intentions.
According to the audio commentary recorded by Jewison for the film's 2005 DVD release, he first became fascinated by the use of multiple screens during the 1967 Expo in Montreal, at which Christopher Chapman's short film A Place to Stand was exhibited. The short consisted entirely of images on multiple screens, and Jewison realized that the technique could be an optimal way to convey several story points without having to focus on them individually at length or employ a complicated montage. The director frequently used the multiple screen technique for The Thomas Crown Affair, most notably during the first bank robbery, when the criminals arrive separately in Boston, contact Crown and then rob the bank. Different actors and actions are seen in small frames within the larger screen, which is sometimes black or filled with other action, and occasionally the smaller frames move in and out of focus to draw attention to other action. Sometimes the same action is seen in multiple small frames that fill the entire screen in a checkerboard effect, as during some shots of the polo match played by Crown and photographed by Vicki. The polo match was partially filmed by mounting a camera onto a chest harness on one of the players, according to the American Cinematographer article.
In his autobiography, Jewison wrote that he hired Pablo Ferro to do the multiple screen work after Ferro designed the credits for his hit 1966 film The Russians Are Coming The Russians Are Coming. Jewison stated that for the work on The Thomas Crown Affair, which had a budget of $4 million, Ferro "came up with a complex process that involved mattes, an animation camera, [and] an optical printer," and that the action was not storyboarded ahead of filming, as was usual. In an information sheet about the special effects, submitted by Jewison to AMPAS so that the picture could be considered for a visual effects Oscar, he estimated that during the robbery sequences, because so much story information was conveyed "in the 3 to 4 minutes of multiple image time, audiences had really been exposed to close to 15 minutes of straight-cut film." Jewison also asserted that The Thomas Crown Affair "was the first feature film to utilize the multiple image effect within a dramatic form."
One of the film's most famous sequences is the chess match between Crown and Vicki, played in the study of Crown's mansion. The scene is played with very little dialogue, rapid cuts and a mixture of extreme close-ups and regular shots. After Vicki defeats Crown, he suggests that they play something else, then kisses her. In his DVD commentary and autobiography, Jewison stated that the chess and kissing scenes took three days to shoot. During the kiss, the camera begins to revolve 360 degrees around the characters, with increasing speed until the action goes out of focus and dissolves into various colors. Jewison related that in order to achieve the effect, Wexler, who used a handheld camera, stood on a skateboard while grips pushed him around the kissing actors. According to studio press materials, the game played by Vicki and Crown, designed by technical advisor Alfred Sheinwald, was based on a real, Grand Masters' match played in 1899. Several reviews of the film compared the chess sequence to the sexually charged eating scenes in the 1963 picture Tom Jones (see below). A clip of the chess sequence was included in the 1979 picture Being There, in which Peter Sellers watches the clip on television and imitates it while romancing Shirley MacLaine. Being There was directed by Hal Ashby, who had served as the supervising editor and associate producer of The Thomas Crown Affair.
The elegant, chic costumes worn by McQueen and Dunaway are another frequently discussed aspect of the film. In contrast to the often hippiesh clothes of the late 1960s, the costumes were designed to enhance the picture's glamor and high style, according to contemporary comments made by Jewison and costume designer Thea Van Runkle, who designed Dunaway's costumes for Bonnie and Clyde. In studio press releases, Van Runkle emphasized what she called the "Method accessorizing" she used in The Thomas Crown Affair to highlight Vicki's emotions, such as a linen suit set off with carnelians and garnets to show that Vicki "was out for blood." Many reviews commented on the lavish outfits, with the Hollywood Citizen-News critic calling Dunaway "a dazzling vision."
The picture received mixed reviews at the time of its release, although it was in the top twenty at the box office for the year, was very popular in Europe and has since become regarded as a classic of 1960s cinema. While some critics applauded the picture's emphasis on style over content, the Time reviewer complained that Jewison has "turned out a glimmering, empty film reminiscent of an haute couture model: stunning on the surface, concave and undernourished beneath." The Variety critic, however, hailed the film as "[w]ell-tooled, professionally crafted and fashioned with obvious meticulous care," and asserted: "A major asset in the story is its essential simplicity, and its lack of plot pretension." Several modern sources claim that McQueen considered The Thomas Crown Affair his favorite of all his movies.
The film received an Academy Award nomination for Best Original Score and won an Oscar for Best Original Song for "The Windmills of Your Mind." The song became very popular, although in his autobiography, Jewison noted that he first asked Andy Williams to sing the song for the film, but Williams demurred and the assignment went to Noel Harrison. Another hit song from the film was set to the love theme heard during the chess game. Alan and Marilyn Bergman later wrote lyrics for the theme, and under the title "His Eyes, Her Eyes," the song has been recorded by numerous singers.
In 1999, M-G-M released a remake of the film, also titled The Thomas Crown Affair. Directed by John McTiernan, the remake starred Pierce Brosnan as a millionaire art thief who is pursued by an insurance investigator played by Rene Russo. Faye Dunaway appeared in the 1999 film in a small role as Crown's analyst, and the song "The Windmills of Your Mind" was recorded in a new version by Sting.