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.

Tootsie is all of those: an unrelenting tragi-comedy dependent on a single actor. Pollack hadn’t done straight comedy until this, and he swung for the fences with the gender-swapping romp. Electric Horseman and his later Sabrina are undoubtedly funny, but Tootsie is a comedy first and a drama second. And it’s somehow still a “serious” comedy, despite the fact that the premise is inherently goofy. The spectrum of films in that specific genre (sidebar: is “gender-swapping” a genre? If “superhero” is a genre then can’t “male-to-female-hero” or “female-to-male-hero” be genres?) aren’t exactly wide-ranging. On one end you’ve got the absurd nonwatchability of White Chicks and Big Momma’s House and on the other you’ve got the super-seriousness of Yentl and Sylvia Scarlett and Albert Nobbs. A very small handful of films manage to make compelling cinema out of the cross-dressing premise, and though special nostalgic consideration may be given for Mrs. Doubtfire it’s really only Tootsie and Some Like It Hot that could be considered for that aforementioned “masterpiece” label.

So one thing that worked in the favor of Tootsie is the maturity of Pollack the director, taking lessons from his earlier selves and besting himself in nearly every case. His comedic timing is incredible, building off the manic unpredictable nature of Dustin Hoffman’s Michael Dorsey. The sheer amount of one-liners in the film is somewhat ridiculous, and it’s possible that can be attributed to Pollack’s precision in the editing room. In comedy film, knowing when to cut can be the difference between a simple quip and a truly memorable line. It combines the actual joke with a visual beat, and in Tootsie that happens at almost every single scene shift. When Sandy panics about not being enraged enough to get into character, Michael’s zippy response — “Alright, I’ll pick you up at ten o’clock and enrage you” — is followed by one of the most jarring cuts of the film. Jarring in a good way, though, in a really good way, in such a way that the whole scene shift is disguised by the fact that you’re processing what Michael just said and laughing about it as the next sequence beings. There are so many of these. Bill Murray’s Jeff upon walking in on Michael with John Van Horn: “You slut.” And later, when Michael reveals himself as Dorothy on live television: “That… is one nutty hospital.”

This leads to another milestone, that of the revelation of Pollack the actor. It’s also fitting: Tootsie, after all, is very much about the trials and tribulations of the actor, the role of acting, the meaning of acting. It wasn’t Pollack’s first time acting, but it is his finest role on the front end of the camera. And that’s no small feat, either, considering the tour-de-force acting opposite him in Dustin Hoffman. His first appearance helps us delve into Michael’s character quite a bit and has the hilariously blunt line about therapy:

And the Russian Tea Room scene serves a similar function, only this time with Michael as Dorothy, and also reiterates the therapy gag:

Pollack’s no-nonsense agent might be coming around to Michael’s absurdly low threshold for incompetence, but only because he’s met with something so convincing — so competent, actually — in Michael’s disguise that he simply has to begin to concede the point. The story goes that on the day of filming the latter scene Jon Voight, with whom Hoffman had starred in Midnight Cowboy a decade or so earlier, was seated elsewhere in the Tea Room. Hoffman approached as Dorothy and acted the part of an adoring fan, gushing and requesting autographs and pictures. Voight had absolutely no idea it was Hoffman.

Tootsie is likewise utterly convincing, which is impressive considering the lighthearted approach to relatively serious themes of gender inequality. Hoffman himself states that he doesn’t consider the film a comedy at all, due to his realization that Dorothy is an interesting woman but not an attractive one, not one he would speak to at a party. Again, this is a dangerous tightrope to walk, often resulting in a clear veer into over-the-top comedy or into deadly self-seriousness. Tootsie manages both and neither at the same time, and in Sydney Pollack’s storied filmography it may yet be his true masterpiece.