The original movie was about a man who was, perhaps, a bit too sold on his own mind.. for better and worse. He seemed to be completely bored with life, but could pull off amazing feats using the intellect alone, and he did -- just for kicks. For example, stealing several bags of cash from a bank without ever getting caught and without having to set foot inside a bank, and when he didn't even really need the money.
Thomas Crown and Vicki Anderson (somebody sent by the bank's insurers to help convict Tommy) have a jeopardous affair, a strange embrace between two twisted psyches that gives the term "sleeping with the enemy" new meaning. It is a "psychological" movie in the fullest sense. Much of the movie hangs on the subtlest nuances.
The characters in the first movie were in some way deeply human and conflicted despite their almost sociopathic extremities, so it wasn't entirely impossible to garner some level of affection for them. The ramped-up characters in the remake were more self-confident, more comfortable, smoother, more decisive in their absurdities -- a bit too self-confident, maybe: they were cold as ice and smooth as stone, almost invariably, and I found it impossible to find any kind of affection for either character, except in particular sparse moments in the film. They had no human vulnerability or warmth to them; there was no meaning to their interactions.
..But no, they weren't graceful enough to be boring. Their antics pulled at the resource of their own mental abstractions over their once-human egos, a language mutually understood by both of them even if, most of the time, they were merely both alone together. There are some sensually passionate scenes in the movie, but I wonder if that in itself is one of the lies that we're sold by the media: that such cold-hearted psycho-mavens can ever actually enjoy passion, that their connection lies just a kiss away..
Basically, for most of the movie its makers merely used the Thomas Crown affair story as a framework in which to proffer more of the same sensationalistic bone-chilling psycho-social foolery that, apparently, Americans are idolizing these days.
The original film was criticized for having a thin plot-line, but I didn't personally see it that way. The film is all about psychological nuance, so whenever there is dialog there is content. The glider scene with the debut of The Windmills of Your Mind was also so fulcral to the whole movie that I'm tempted to consider everything else in that movie, past and future, to be merely context-setting for that one consummate moment (now that's what separates a box-office hit from a cult classic..).
By contrast, the 1999 version didn't quite have the same charm, being just another Hollywood ego-sater (they didn't even have The Windmills of Your Mind sung for any scene, because they knew they couldn't live up to that), but I'll hand it to them: their story of the heist was much more enthralling and intricate and demonstrative of Thomas Crown's genius. However, the heist wasn't the only aspect of the story they changed.. they diametrically changed the ending from a sad one to a happy one, which was 90% of the movie's message in the original film, so it's basically not even The Thomas Crown Affair anymore. It's another lucrative Hollywood endeavor.
The first story was bittersweet and highlighted the weakness of the mind to immediately change its course, however much one might want it want to. The 1999 story included some of that, but it wasn't poignant in the same way, not being in the denouement of the film. The first film also showed Tommy Crown's amazing guile and altruism in allowing his potential companion to decline; the second film allowed him to use his skill to break her down and cajole her into trusting again -- with no possible sacrifice for him, and they both assumably lived happily ever after.. though on rather tenuous bases, if you ask me. Or if you ask his therapist -- who, interestingly enough, was played by the same woman who played his lover in the previous film, now 31 years the wiser. (Quote: "If you've found a female mirror image, and think you're going to form a rewarding relationship..")
Overall, I think the first incarnation of the film is a "cult classic" for a reason. The second film was just too cold, for the most part, to empathize with the characters, though the whole process where he established trust between them, once and for all, was very touching. Also, the original film was fraught with all the tensions and perils of being human; in the second, they were both übermenschen to everyone else and to its audience, knowing only secretly, somewhere deep down (or maybe only occasionally, for the script), that they had truly only lost their way home. Actually though, to be honest, only she knew this in the 1999 version. In the 1968 version, perhaps, in his own way, only he knew.
BTW, here's a Radiohead music video that these two movies reminded me of.