Steve McQueen, the epitome of cool in that era to me, was the star, along with Faye Dunaway. As a movie, it was not great, but it was the Boston of 1968 that was great to see. You'd have to watch it several times to catch all the scenes, but they include Beacon Hill, the Mass Pike, the Cape, Myopia Hunt Club ... actually I didn't really hang out at Myopia much.
The movie is also a "screen capture" :-) of the fashion of the era, in clothes, cars, interior design, etc. There have been a flurry of movies set in Boston recently -- The Departed, Gone Baby Gone among them -- but The Thomas Crown Affair is fun to see. Here's some more info about it.
Any other movies you recall set in Boston in the 1960s?
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