* OneSceneWonder: Well, technically a ''Two''-Scene Wonder; Creator/GeenaDavis (in her film debut) as the sexy, underwear-clad costar sharing Dorothy's dressing room.
** One of Creator/GeenaDavis' earliest roles as "Dorothy"'s castmate.
** A pre-''[[Series/TheGoldenGirls Golden Girls]]'' Estelle Getty has a bit part as one of the couples seen dancing late in the film, and is pretty recognizable.
* TrueArtIsIncomprehensible: In-universe, this is very much Jeff's philosophy towards his playwriting.
-->'''Jeff''': I don't like it when people come up to me after my plays and say, "I really dug your message, man." Or, "I really dug your play, man, I cried." You know. I like it when people come up to me the next day, or a week later, and they say, "I saw your play. What happened?"
* ValuesDissonance: Granted, it's nowhere near as bad as other comedies in which the plot hinges on a cishetero man pretending to be a woman (we're looking at you, ''[[Film/AceVenturaPetDetective Ace Ventura]]''). Still, with the rise of visibility for transgender people, many of whom are frequently dogged with accusations of "pretending" to be a different gender, it's a little harder to find humor in this premise. It doesn't help that it's near impossible for trans actors to get roles reflective of their genders, up to and including ''as'' trans characters.
* ValuesResonance: And on the flip-side of things, Hoffman gave an interview with AFI [[https://www.today.com/popculture/dustin-hoffmans-tearful-tootsie-interview-about-women-goes-viral-6C10578440 in which he broke down crying]] when he had a HeelRealization.
-->'''Hoffman''': When we got to that point and looked at it on screen, I was shocked that I wasn't more attractive. I said, 'Now you have me looking like a woman, now make me a beautiful woman.' Because I thought I should be beautiful. ... And they said to me, 'That's as good as it gets.' It was at that moment [[EurekaMoment I had an epiphany]], and I went home and started crying, talking to my wife. And I said I have to make this picture, and she said, 'Why?' And I said, 'Because I think I am an interesting woman when I look at myself on screen. And I know that if I met myself at a party, I would never talk to that character because she doesn't fulfill physically the demands that we're brought up to think women have to have in order for us to ask them out. She says, 'What are you saying?' I said, 'There's too many interesting women I have not had the experience to know in this life because I have been brainwashed. That movie was never a comedy for me.'
** Unfortunately, all of this is much HarsherInHindsight after a wave of [[http://variety.com/2017/biz/news/dustin-hoffman-2-1202641525/ sexual harassment and assault allegations]] directed towards Hoffman surfaced in 2017.