This is one of those films I've heard about all my life, but never seen before. It came out when I was very young and was very highly regarded, so I was looking forward to have the chance to see it and see if it lived up to those standards. I was a little worried a cross dressing comedy might not hold up too well in today's modern world, but I have to say my worries were unfounded.
This film is really more drama than comedy. While there are some funny moments, this is not the outright silliness of something like Mrs. Doubtfire though it's also obvious that that film took a lot of influence from this one. This is primarily the story of struggling actor Michael Dorsey, who dresses like a woman to get a job because his reputation prevents him from getting a job as a man. While he originally does it as an excuse to make some quick money, he ends up learning a lot about himself as well as about women in general.
Bill Murray appears in the film as Dorsey's roommate Jeff, and this is probably the most serious role he's played up to this point. He is still there for laughs, but they're far more subtle laughs than the goofy groundskeeper in Caddyshack or the devil may care wiseguy from Stripes. He's a playwright of the most pretentious caliber, explaining to friends in one scene that he doesn't want people to come up to him and say "I dug your play" but rather to have them ask "What was that?" It's a good spoof on these type of artists. He also often becomes the voice of the audience when talking to Michael, questioning him if maybe he's taking his pretending to be Dorothy Michaels just a little too far.
The story also works pretty well as an examination of feminism and gender roles, as Michael shakes up the soap opera status quo by being a more independent woman on the show without falling into the role of ice queen, thereby inspiring women who watch the show everywhere. He also tries to inspire his coworker Julie to get out of the relationship she's in with their womanizing boss. It creates an interesting duality as Michael is not only lying to his coworkers and most of America watching the show, but he's also doing his own lying and womanizing to an old female friend of his at the same time. Add to that the layer of his coworker's widowed father trying to court him, and the film ends up with a lot of layers but handles them all really well.
Another problem that can happen with a film like this is how it ends. With this level of deception, can relationships truly be repaired once the lie is revealed? I think it manages to handle that pretty well, giving Michael a little bit of hope to have a relationship with Julie (who he of course fell in love with, what else would you expect?) but also not having her forgive him 100% either. I also like that he at least tries to apologize to her father, though I can't help but think a traditional man like that would realistically not want to associate with him at all after everything that happened.
Overall, I was pleased with Tootsie, finding it a good drama with some nice touches of humor here and there. If you've never seen it before, I recommend giving it a watch.