Sydney Pollack and Robert Redford collaborated on seven commendable films over a 24-year period — This Property Is Condemned (’66), Jeremiah Johnson (’72), The Way We Were (’73), Three Days of the Condor (’75), The Electric Horseman (’79), Out of Africa (’85), Havana (’90).
There’s no question that the top three and the hottest streak happened between ’71 and ’75 — a four-year period that gave birth to Jeremiah Johnson, The Way We Were and Three Days of the Condor. Which of these are the best? It’s a close tie between Condor and TWWW. I’ve always leaned towards Condor because I can’t stand Bradford Dillman‘s WASPy character…literally chalk on a blackboard whenever he appears.

In these seven films Redford is “always the same character,” Pollack told Charlie Rose in ’93. “To me he’s a throwback to the actors I was nuts about when I was growing up and going to movies. A real classical, traditional, old-fashioned movie star who was very, very redolent of some kind of American essence, if you will. Very much a part of the American landscape. Heroic in a kind of understated way.
“And I was really fascinated with [the realization[ that all of the characters he played in these films are the same character. He’s gotten older and older and older and gone to different places…sometimes he’s out west, sometimes he’s in Africa, sometimes in New York, sometimes in Cuba…but he’s the same character.
“Number one, he’s a man who doesn’t want to give up any of himself in order to have a relationship…which costs him severely [as] he’s always alone, ultimately. And number two, he doesn’t want to live in a society in which he has to subjugate his own individual needs for the purposes of some collective authority. So he’s usually on the edge of an uncivilized airier territory. It’s why he’s a mountain man…it’s why he’s in Africa. A guy who believes it’s possibly to have relationships but doesn’t really understand what he has to personally give up…an individualist in the sort of real, generic, basic sense of the word.”