My wife had never seen it. I feel like Tootsie is a technical triumph in many ways and I wonder how many movies do so many things this well. Most obvious is Hoffman's masterful performance here, which is confusingly good. When he's Dorsey playing Dorothy, you totally believe Dorothy is real and you forget the role is really Dorsey. When he's Dorsey, he's also typically believable. Sometimes, often, he pulls this incredible trick of showing you Dorsey in Dorothy. Then, not only is he somehow two different people in one, he's also the great actor being played by the invisible great actor underneath it all.
Now, name me any other actors who could have done this? I've never seen Mrs. Doubtfire so I've no idea if Williams was this good, or meant to be this good in this way.
Then there's the script (written by a crack team including the great Larry Gelbart, the great Elaine May, the great Barry Levinson) to this which is, again, a technical masterpiece of Hollywood. I'm sure this used to be in textbooks as, well, a textbook example of a nearly-flawless conventional 3 act script. It manages to juggle all these balls in the air, setting up these great scenes of suspenseful comedy whith almost too-many-to-believe character connections and points of drama. Everything comes together effortlessly in this script. It really is mesmerizing.
Finally, there's the directing by Sydney Pollack, who also plays Dorsey's agent. Pollack is in complete control of this material and he really is a whiz at making all these pieces work together. It's not an easy feat to depict a show within a show, as well as the behind-the-scenes workings of a show, that seems convincing. Pollack does it. How does he manage to bring it to life with verisimilitude AND gut-aching laughter? He gets all the timing right.
Having said all this about Tootsie, one can't fail to notice upon watching this movie that there is little chance it could be made today and that this movie probably falls into the "cancelled" category that takes up so much space in today's cultural landscape. Tootsie likely goes into the town dump of political correctness and social media.
Should it? Should I even have been laughing along with this? I think the twitterverse would likely say "no." It's worth it to ponder the question of why and what's so wrong with this movie in today's context. Leaving aside Hoffman's own #metoo canceling, maybe today's zoomers would just find the whole premise of Tootsie offensive as well as several of the plot lines?
