The Thomas Crown Affairs 1968 vs 1999

vs.

One might ask the question: "Why watch both versions of The Thomas Crown Affair back to back?" My answer to that question would be: My wife has a thing for Pierce Brosnan and I like Faye Dunaway.
But it is not that simple. Beneath the surface glitz and wish-fulfillment of the premise of both films lurks a darker side of trust and competitiveness of the power-players in Western Culture. This hasn't really changed in 30 years, other than perhaps the way mainstream entertainment presents them.
In the Original 1968 version, both the characters (Steve McQueen and Faye Dunaway) are given a cruel edge to their characters who ultimately double-cross each other out of any meaningful relationship because they can't trust one another. In the 1999 version, the same thing happens, but somehow it's OK with the girl (Renee Russo) who finds it charming and just another way continue the game. It gives the edge to the 1968 version.
Undoubtedly the 1999 version is much glossier, including both heists in the film are far more fluid and watchable. But the core of The Thomas Crown Affair is the relationship and foreplay of the leads. The 1999 version is just to obvious. The chess match in the original (I mean what is less sexy than Chess? -- That is why this scene works.) is replaced with some hot Tango dancing, eliminating the irony and reducing the effect of the sequence. The 1999 version also cheaps out with the 'other woman' making her asexual (Crown is her legal guardian -- and doesn't behave like Woody Allen). In the first one, McQueen's Crown does it just to spite and shake up Dunaway's character.
It is no surprise that the original is directed by a 'drama' director, Norman Jewison and the update/remake is directed by an action director, John McTiernan. The nature of the director underscores the strenghts and weakness of each version. I guess the Auteur theory is good for something.

You could do worse for a mainstream old-style star-vehicle, Like say, both versions of I Love Trouble, or both versions of Oceans Eleven (ok, ok, the Soderberg version is watchable in the same way the 1999 The Thomas Crown Affair is).