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@gol_d_berg @Twoinchdestroya Hmm, maybe? In Naruto, the "pervy sage" trains Naruto under the condition that he promises to transform into a naked female version of himself. It was obviously a joke (not for approval), done for laughs to show us how this otherwise incredible man can succumb to his own crippling and human vices. I think we all get what was going on here, it's not flying over kids heads. We don't really see characters like this today, whereas the "pervy old man who is also an expert you have to work with" was a pretty common character before.
I don't think something like this could get made today, especially in a show targeted at pre-teens, and if they tried it would probably be forced to heavily imply that Naruto was actually trans.