The Thomas Crown Affair [1968, United Artists/MGM, color], which is traditionally referred to as a "heist" movie, was in actuality a kind of romantic comedy with black comic undertones. The remake, not unsurprisingly, was a pathetic rehashing of the crudest, and least interesting aspects of the original story, not least (I suspect) because that first cast was uniquely suited to its purposes, and couldn't simply be transmuted, or re-adapted with new bodies in fixed roles.
The Director, Norman Jewison, was already a seasoned movie mogul by the time he did this film--he'd been directing and producing work since the early 1950's--and he'd directed McQueen in The Cincinnati Kid  just three years earlier. Jewison, it should be noted, wasn't a one-trick pony, having also done The Russians Are Coming , In the Heat of the Night , Fiddler On the Roof , and Moonstruck .
McQueen, whose career had not kicked into high gear until The Magnificent Seven , had built an impressive screen presence and career with The War Lover , The Great Escape , and The Sand Pebbles , but he'd begun to be typecast as a macho action figure, a bankable profile, still dangerously limiting for a serious actor. Straying outside what was becoming his usual type carried risks. As originally conceived, Thomas Crown was a polite, refined playboy. Could McQueen bring it off?
Faye Dunaway, McQueen's rival and love interest in the film, was just beginning as an actress, having only completed Bonnie and Clyde  the year before, and whose career would not really blossom until the 1970's. Once again, improbable casting put two unlikely actors into a situation that few would have predicted could work.
Outwardly, the plot is filled with fantasy. Thomas Crown, a spoiled, bored rich kid (banker) living alone (divorced) in a Beacon Hill mansion, decides to pull off a bank robbery, just for kicks, and to prove that he's smart enough to beat "the system." Traveling to Europe, he deposits the cool 2.6 million in cash in a numbered account in Geneva. Vicki Anderson [Dunaway] is brought in by the insurance company to investigate. Vicki immediately spots McQueen from among the suspects, and sets out to pursue him, instigating a romantic affair, which is complicated by the fact that she's convinced he's the guilty one. In due course, the "affair" becomes a complex fencing game in which both test each other's commitment to each other. Crown decides to pull off another heist ("I can do it again"), preparatory to disappearing into Europe, and as a gambit to force Vicki to choose whether or not to be his companion or turn him in for the reward.
The filming, which was done on location in and around Boston, and in other areas in Massachusetts, has an authenticity which belies the hip cinematography--quite innovative for its time--which involved split screen projection, multiple frames, and a jazzy, flowery score by Michel Legrand that gave the whole production a brisk, up-to-date flair.
The seduction scenes between Dunaway and McQueen were stylishly conceived. A game of chess, a romp in a dune buggy on the beach, a walk in the old Boston Cemetery. The sexual chemistry between these two, derived from their respective characters' mutual frisky approach to life, is the fulcrum which balances the film, between fluffy sexual dalliance, and the pursuit of crime/and criminals, which is the ostensible engine of the narrative. They're playing with each other, but the game is deadly serious. We know, on the one hand, that Crown is much too selfish and wayward to capitulate and go to prison--for love; but Vicki Anderson may wobble: Tommy's offer of a future of naughty escape into elegant decadence and devil-may-care tests her limits. Will she be a good girl, or join him in picturesque, existential rebellion?
Coming, as it did, towards the end of the 1960's, the counter-cultural undertones may seem odd today. Did anyone believe that a Boston banker could harbor anti-social tendencies of this magnitude? Was Tommy's antsy-ness, his feeling "trapped" by a circumscribed social and economic strait-jacket a believable portrayal? Almost certainly not. What McQueen brought to the role was his fine sense of mischief, an elf-like mercurial spirit which lent the part gusto. Against his shrewd, suave assurance, Dunaway's stylish, fashionable feminine mettle and polite coyness and strategic persistence may have seemed pale. Dunaway was at the height of her beauty and polish at this point--she seemed almost like a platinum Scheherazade.
In the 1930's, at the height of the Depression, American audiences were treated by Hollywood to visions of sugar-plums, as upper-classmen in tuxedos sipped cocktails and wisecracked to smart, felicitous ladies in furs, as New World royalty hobnobbed through penthouses and were whisked about town in saloon cars. In The Thomas Crown Affair, Vicki represents cheap, tawdry "new money's" envy of Tommy's olde world, settled, traditional accoutrements--his 200 year old mansion on Beacon, his beach house on the Ipswich Dunes, the Copp's Hill Cemetery in North End (where his forbears are undoubtedly buried), the staid, wood-paneled auction house, the polo match at Myopia Hunt Club in South Hamilton, his personal glider, his Rolls, his giant corner office, etc. Audiences could see and appreciate all this splendour and insolent gratification, without the least sense of guilty pleasure, since Crown had come into his money the old-fashioned way (he inherited it), and he was now renouncing a way of life that inheritance had made incumbent. Tommy wasn't the typical rebel--the Marlon Brando of The Wild Ones , or James Dean of Rebel Without a Cause  and East of Eden --his rebellion consisted of a rejection of privilege, of the responsibility of wealth, of a duty implied in the capitalist social contract--politics, finance, charity, the courtesies of ceremony--all the things he finds tedious and passe. In this respect, The Thomas Crown Affair is decades ahead of its time, in positing a renunciation of wealth and advantage; and this was made particularly evident by the stilted remake of 1999 with Pierce Brosnan and Rene Russo. By then, there was no longer any novelty about breaking the law: After all, crooked Wall Street Traders and investment bankers, drug lords and Mafiosi and Black gangstas had already become de rigeur in American cinema. Crime had long ago ceased to be a road to respectability. Who wanted to be respectable, for God's sake, when being naughty was so much more fun?
In Thomas Crown, Steve McQueen made contempt for affluence hip, and trendy. Underneath his trim, molded exterior there lived a stealthy panther of a creature, attracted not to authorized pleasures, but to guilty indulgence.
Tommy's personal crusade was against "the system"--not against injustice, innocent suffering, or rivals--but against the boredom of predictable, secure existence. McQueen's signature rascality, his Outsider's brash confidence, and ruthless pursuit of selfish fulfillment, was brilliantly elaborated in Thomas Crown. No longer merely the intrepid action hero bumping off devils and throwing over swooning maidens, not just the audacious stunt man risking life and limb to prove his upstart manhood.
Typically, audiences may have wished that this cock-eyed love affair could end up in heaven, but logic dictated otherwise. In one scene, Tommy and Vicki are lying in bed while he smokes a cigar, contemplating his next bank job. "I can do it again," he boasts. Vicki, frustrated and looking for a compromise that will allow them to stay together, asks "why?" "The system," he replies, "me, and the system." "But why?" she insists. "It's my funeral. You're just along for the ride." This declared sense of fatalistic power, expressed with an infernal resignation, transcends the moral universe beyond which even someone as pragmatic and courageous as Vicki can't follow. Tommy has crossed a line, not just in the society he inhabits, but in the movie universe of allowable outcomes and choices.
When Tommy betrays her confidence, in the end, leaving a note that allows her--if she chooses--to join him in Switzerland, or to keep his Rolls and the loot from the 2nd bank job, as he snoozes on his trans-oceanic flight back to the Old World culture, we realize they have, in effect, now both relinquished not only the possibility of love, but of the fruits of the American Dream.
America was founded upon (or later expanded to include) the principles of economic opportunity, of the equality inherent in an ideal classless society in which race, gender, creed, color, religion, and national origin would not be a basis for prejudicial exclusion. Our laws are designed to enforce (sort of) these principles, to insure a level playing field in the pursuit of happiness (and wealth and fame and power). The Thomas Crown Affair deigns to suggest that this paradigm is flawed; that, beyond success and ultimate means, there lies a further boundary of contention, in which the experience of life's potentiality is played out on another field of mastery, where you make the rules up as you go along, where the limits are determined by one's imagination and guile.
For such individuals, love, the natural affection which men and women feel for each other, may become a casualty, may, in the end, signify nothing more than the camaraderie of team spirit, of mutually interested parties, willing to betray each other in the final gambit. The chess game which the two play symbolizes the rules of the dirty little game, the inevitable romantic interlude, and eventual dissolution. As an avatar of selfishness which Thomas Crown stands for--McQueen's lone wolf profile--who lives by his own code of honor and dignity and physical exhilaration, whose playthings are women and toys and other people's money--there's no better example in the history of cinema (except, perhaps, Cary Grant's Mr. Lucky). "Money isn't funny," he says at one point in the film. He's right.