Tootsie was a milestone for Sydney Pollack for a variety of reasons, some of which were trumpeted by adoring critics in 1982 and some of which took the ensuing decades to gestate. Today, with the benefit of Pollack’s entire career in retrospect, Tootsie holds strong as one of the director’s finest achievements. It is arguably his masterpiece, sure, but perhaps more significantly it is arguably his first masterpiece. That’s important for a film about a struggling actor finally doing what is necessary to create his first unadulterated success, finally testing himself to a limit he’d never considered before, being rewarded for it, and unexpectedly touching other lives along the way.
Of course “masterpiece” is relative. Three Days of the Condor might be a masterpiece, as might Jeremiah Johnson to a somewhat lesser extent. One of Pollack’s unsung achievements is The Electric Horseman, not a masterpiece in and of itself but masterful at times nonetheless. Saying one is better or worse than the other is uninteresting. What’s truly fascinating — and what makes Pollack one of the greatest American directors of his time — is the clear way in which elements of those earlier films come together in collaboration on Tootsie. Consider the most basic triumphs of each of those three films: Condor was unrelenting from start to finish, Jeremiah hung itself on the power of a single actor, and Horseman was simultaneously a comedy and a tragedy.