Uneasy lies the head which wears the Crown: 1968 vs 1998...
Okay, one point I think most people would agree on: despite its historical value, the 1968 version has aged badly. That is about the only bad side I can see and even that doesn't detract much from the movie for me.
The 1998 remake seemed almost pointless to me. Although perhaps someone thought it worth updating, the end result was worth less than the effort expended. To make it worthwhile, it is necessary to understand what makes Thomas Crown tick.
In the 1998 version, Pierce Brosnan is this happy-go-lucky, loveable guy with the Midas touch. We like him because he's rich and successful and above all, self-made. He's even got his name on the building. If there's a dark side to him, it is hidden too deeply in the mush of opulence and self-indulgence which headlines this version. His hobbies reveal him to be very active and motivated but when he trashes his toys, it smacks of conspicuous consumption. He does all these things because he can.
In the 1968 version, Steve McQueen's character is bored. Some have even suggested he's depressed. The scene at the gliding field reveals a lot about him. He's taking unnecessary risks - like the low approach to the field - because he doesn't care. He intimates to Gwen he's having a hard time deciding who to be tomorrow.
I'm no psychologist but this seems a much more powerful and believable reason for instigating a robbery. He's good at everything he does. He's done everything he can do in his life and there are few significant challenges. Vicky is one challenge but even then, he's still got Gwen when he wants her.
McQueen's Thomas Crown despises the big shots he works with ("You're over paid"), which would be in line with the attitudes of a lot of self-made people. And he's hard, not just in the stereotypical Hollywood version of a businessman way either. He's bored. His marriage went belly-up. What does he really have to live for?
Ultimately though, Vicky is good for Thomas and vice versa, which is why he tests her. In the '98 version that test is just a standard plot point. It's so clumsy that the only thing it tested was my patience...
In the end, I don't blame Pierce Brosnan for the 1998 version. They just made him inane, which wasn't his fault. Seducing the audience with self-indulgence and conspicuous consumption didn't allow me the luxury of deciding what goes on inside Thomas Crown's head - not the way it did in the '68 version, anyway. In comparison, the '98 version just doesn't cut it. It was a puff piece made for lazy, unimaginative audiences who don't like to be challenged into thinking or be disappointed at the end. Lots of style; not much substance.
McQueen said it was his best performance. I agree.