When is a caper movie not a caper movie? Norman Jewison's 1968 classic "The Thomas Crown Affair" opens with a thrilling bank robbery that wisely races by you so quickly (thanks to Pablo Ferro's title design that frames the film.) Ordinary action is made to feel foreign, dare we say "New Wave." Haskell Wexler's artistic cinematography makes taking phone calls in a public booth into lightning transactions along high-tension wires. Seeing Steve McQueen's mouth pause and then utter the word "Go!" could cause palpitations. However, as beautifully orchestrated as this broad daylight/downtown Boston/nothing-but-small-bills-please heist is, when the action pauses - you have so much time to wonder why.
So, as millionaire Thomas Crown moves all of his employees, help at home, and hired guns around like chess pieces (matching the film's most memorable and steamy scene later with Faye Dunaway,) after all is said and done - he merely sits alone with his martini and cigar laughing. Outside of the upcoming foil of investigator Faye Dunaway, even the Boston Police evaluation of the crime is well-organized. We all know that a successful robbery must be well-timed (go back to 1903's "The Great Train Robbery" and see for yourself.) Furthermore, that timing extends in modern cinema to skillful editing and direction that keeps you on your toes. However, there is a purpose in McQueen's solitary explosion of laughter.
Screenwriter Alan Trustman once worked at a downtown bank in Boston in 1954. After becoming a lawyer, his office was directly across the street. This slight change in location and a move up the corporate ladder lead to his daydreaming about a "thrill-seeking" heist. The mechanics captured are almost too easy. Catch the end-of-week transfer to the basement at just the right time - and disappear in the fumes of the smoke bombs you use to cover your trail.
Still, there is no "Why?" Crown hires random skillful petty thieves who do not know each other - and never will. Furthermore, Crown, cloaked in darkness and using an altered voice, even tells the getaway car driver (Jack Weston,) that if at any time he does not want to follow through anymore - he can walk. Is this Crown's skillful manipulation of people to do his bidding as if it were their own or is it proving to himself that his level of due diligence is unmatched? (Similar to when a math/techie wiz reports that their numbers are up, so Crown cavalierly throws him the files in his hand to give a whirl.)
Knowing Trustman rewrote the entire screenplay to fit McQueen, and Jewison had already worked with him before, one cannot help but think the anti-hero they are building in Thomas Crown portrays far more than a white-collar criminal who wants to get as close to being caught as possible. Trustman could be the mild-mannered man in the grey flannel suit who needs to free himself from the rigors of daily life. Jewison goes even further into either separating himself from previous social (1967's "In The Heat of The Night") and political (1966's "The Russians Are Coming, The Russians Are Coming") filmmaking.
As always in the Sixties, film may not quite be able to provide complete escape velocity from the larger events of the day. Watching it fifty years removed from its original summer run, "The Thomas Crown Affair" may be read as a statement regarding the futility of the world unfolding. Crown, has everything and everyone at his disposal. Obviously, he could quit his "job" and live off the interest his vast wealth earned for the rest of his life. Alas, where is the thrill in that? Racing dune buggies is not necessarily death-defying, but putting yourself on the line as a thief is. As Dunaway gets closer to what she knows to be the truth, her possible addition to the scheme is an added layer of deception and/or excitement.
With everything provided at his beck and call, with every whim immediately met, Crown's only true rush would be knowing that he could lose it all. All his efforts, calculations, and painstaking detail would prove to be wrong for one iteration of this cycle. In addition, Crown would possibly lose everything he has. Certainly, the government case against him would leave him with some money in his coffers - possibly enough to savor the faintest taste of his previous life after a few in a cell. However, trading his three-piece suits for the itchy blue denim of a prison uniform would be no comparison to all the time behind bars. All those hours, dreaming up another seemingly impossible scheme whose non-application would diminish the rush to the point of failing to block out the hostile reality of time served.
So, he is laughing all right. Not laughing at how easy it was to conduct this symphony of larceny, manipulation, and deceit. Crown is laughing because he avoided tumbling off of the high-wire act of his secret life, while knowing that waiting below him - is no conceivable net.