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Millionaire Thomas Crown (Steve McQueen), who doesn't need the money but who loves the challenge of stealing it, pulls off a heist by hiring five thugs, none of whom have ever seen him, to steal over $2,600,000 from The Boston Mercantile Bank and deposit it in a garbage can in a cemetery. The perfect crime. However, insurance investigator Vicki Anderson (Faye Dunaway) is certain that the thief is Thomas Crown and intends to prove it. Things get complicated when Vicki and Thomas fall in love with each other.

The Thomas Crown Affair is based on an original screenplay written by American screenwriter Alan Trustman. A remake, The Thomas Crown Affair (1999), was released in 1999. An interesting tidbit about Trustman says that, when he was 15 years old, he had a low-level job at a bank. He used to sit and wonder how someone could go about robbing it. He later used this knowledge to craft the heist scene in this movie. The scene was evidently so accurate that the bank where Trustman once worked refused to let the production film there for fear of a copycat crime. Read more here.

Thomas Crown is a 36-year-old millionaire who made his money in investment securities and real estate but occasionally pulls off bank robberies. His hobbies include playing polo and gliding. He lives in the Beacon Hill section of Boston, Massachusetts. Some have likened him to James Bond, which is interesting because Sean Connery was actually one of the actors considered for the role of Thomas Crown. (Peirce Brosnan wound up playing Crown in the remake, after playing Bond in Golden Eye and some of its sequels.)

Vicki and Detective Eddie Malone (Paul Burke) came upon Crown's name by cross-checking airline records to see who had traveled to Switzerland multiple times since the robbery. Thomas was one of eight suspects, and Vicki's instincts told her that he was the one.

The song being played during the opening credits is The Windmills of Your Mind, music by French composer Michel Legrand, lyrics by American songwriters Alan and Marilyn Bergman, performed by British actor and musician Noel Harrison. Legrand won an Academy Award for Best Song with Windmills of Your Mind.

The sailplane (N9860E) that Crown is flying is a Schweizer SGS 1-23H-15.

A 1967 Ferrari 275 GTB/4 NART Spyder. On page four of the Motor Trend article, it states, "It's no wonder the producers determined there wasn't a better car for Ms. Vicki Anderson to catch the attention of one Mr. Thomas Crown."

10% of everything recovered. If she recovered the entire amount, $2,660,527.62, she would receive $266,052.76. However, Thomas had to pay off his accomplices, so Vicki's take would probably be less than that.

Thomas came to realize that he was going to have to liquidate his assets and move to some other country, because Vicki and the cops were getting too close. He's enumerating the pros and cons of going to Brazil. The samba is a traditional Brazilian dance, and Sugarloaf is a mountain in Rio de Janeiro. Those would be the pros. Cons would be the jungle and the fact that piranha are found in the rivers of the Amazon basin.

Thomas decides to carry out a second heist in much the same fashion as the first one. As a test of Vicki's faithfulness, he tells her that the pickup point will be in the cemetery. Vicki passes on the information to Det. Malone, and they sit in a car watching. The heist goes off without incident, and the money bags are dropped in the trashcan. Two agonizing hours later, Thomas' Rolls Royce shows up to retrieve the money. The police box in the car but find that it's being driven by a messenger bringing a telegram for Vicki. "Left early," it says. "Please come with the money or you keep the car. All my love. Tommy." Meanwhile, Thomas can be seen seated in a jet plane on his way to who-knows-where. Half-laughing and half-crying, Vicki rips the telegram to shreds and tosses it to the wind. Thomas smiles slightly to hold back his tears.

The split screen technique was a popular trend in the 1960s. Split screens were used previously in such movies as Pillow Talk (1959), Grand Prix (1966), and A Place to Stand (1967), a documentary produced for the Ontario pavilion at Expo67, the Montreal World's Fair. Split screen was used the same year in The Boston Strangler (1968), and again in Goodbye, Columbus (1969), Airport (1970), and More American Graffiti (1979).

Viewers who have seen The Thomas Crown Affair have mentioned several movies that show good bank heists, including: Bonnie and Clyde (1967), Kelly's Heroes (1970), The Getaway (1972), Charley Varrick (1973), The Outfit (1973), Dog Day Afternoon (1975), Point Break (1991), Killing Zoe (1993), Heat (1995), Entrapment (1999), Sexy Beast (2000), Inside Man (2006), and The Bank Job (2008). Some other good heist movies, although set in places other than banks (e.g., jewelry stores, museums, casinos, trains, etc.) include: The Asphalt Jungle (1950), Ocean's Eleven (1960) or the remake Ocean's Eleven (2001), Band of Outsiders (1964), The Hot Rock (1972), The Great Train Robbery (1978), Die Hard (1988), Reservoir Dogs (1992), and The Usual Suspects (1995).

The hit United Artists film, The Thomas Crown Affair, opened on New York's Broadway at the Astor (a Walter reade theatre), and two other theatres in New York, on Wednesday, June 26, 1968; it ran several weeks.