The distinction between "hopping" and "blurring" that line is a bit hard to reckon because male and female are still very concrete categories over there (remnants of Taoism, yin/yang and all that). I'll leave that tangent aside and try to directly answer your question:
From antiquity there's been several Shinto deities that are variously depicted as male, female or androgynous.
Traditionally, women were barred from acting in Kabuki theater, so all the female roles have been men in makeup for a few hundred years. (I'd have to check if there's been any slackening of this rule in the last decade or so) Side note: women are historically very involved in all sectors of entertainment by playing instruments, singing, dancing, reciting poetry, etc...
There was plenty of homoerotic business being conducted in the Yoshiwara red-light district of pre-modern Tokyo (Edo), much of it involving cross-dressing.
As for anime, I'm sure there's many more, but here are some examples I know of:
As far as I can trace back, the original trap is Hibari-kun (1983)
That same year saw the introduction of Ryūnosuke from Urusei Yatsura.
I won't spoil anything about Gall Force: Eternal Story (85) except to say that it's germane to the discussion. Really great film, been watching it for 25 years. The song for the credits reel includes the line "You probably think I'm a crazy feminist." I've got the soundtrack CD.
Dirty Pair: Project Eden (86) makes a passing reference to sex-change surgery in a distant future where the technology for something better than an axe wound is hypothetically feasible. Also a really great example of peak '80s anime.
Zoisite from Sailor Moon (92) is a very interesting case. You can easily search up clips of his original Japanese voice, then a female English dub from the '90s (which had me completely fooled back in the Toonami days), then once again male for an updated English dub in 2014. Don't miss the irony that the West was censoring homoerotic romance from globally popular anime at one point in time.
By far the most famous instance of that was in S3(94) when the first English dub portrayed thesetwo as "cousins" rather than...y'know.
Then in S5(96) the Japanese showrunners actually made a slight adjustment from the source material. In the manga these three are girls pretending to be boys, but in the anime they're depicted with bare masculine chests at the beach, implying that they transform into girls when assuming their "sailor warrior" forms. The manga author has gone on record as being a bit annoyed about this because her intention was for it to be a "girls only" thing.
Eps. 12&13 of Cowboy Bebop (98) feature the kind of dramatic character you were discussing with u/altmehere (seasoned with a bit of comedy from other background Ts). But do go in for the whole show or none of it at all - it's essential Weeb 101 material. I'll even endorse the dub. Oh and also, the Netflix remake sucks and everyone who truly appreciates the original hates it.
I think I've made my point, even if I stop a decade earlier than you requested. I do recommend this rap battle for some tongue-in-cheek modern "trap" culture (as opposed to WT culture)
You weren't exactly wrong about the T propaganda thing. As you well know the net is infested with them. A huge portion of them have anime avatars, and just like everything else they think anime should be all about them, source culture be damned. But hopefully I've demonstrated that you can tell an honest weeb from an ego-tripping troon by looking for subtlety, nuance, humor, open-mindedness, simple fun, etc...
The distinction between "hopping" and "blurring" that line is a bit hard to reckon because male and female are still very concrete categories over there (remnants of Taoism, yin/yang and all that). I'll leave that tangent aside and try to directly answer your question:
From antiquity there's been several Shinto deities that are variously depicted as male, female or androgynous.
Traditionally, women were barred from acting in Kabuki theater, so all the female roles have been men in makeup for a few hundred years. (I'd have to check if there's been any slackening of this rule in the last decade or so) Side note: women are historically very involved in all sectors of entertainment by playing instruments, singing, dancing, reciting poetry, etc...
There was plenty of homoerotic business being conducted in the Yoshiwara red-light district of pre-modern Tokyo (Edo), much of it involving cross-dressing.
As for anime, I'm sure there's many more, but here are some examples I know of:
As far as I can trace back, the original trap is Hibari-kun (1983)
That same year saw the introduction of Ryūnosuke from Urusei Yatsura.
I won't spoil anything about Gall Force: Eternal Story (85) except to say that it's germane to the discussion. Really great film, been watching it for 25 years. The song for the credits reel includes the line "You probably think I'm a crazy feminist." I've got the soundtrack CD.
Dirty Pair: Project Eden (86) makes a passing reference to sex-change surgery in a distant future where the technology for something better than an axe wound is hypothetically feasible. Also a really great example of peak '80s anime.
Zoisite from Sailor Moon (92) is a very interesting case. You can easily search up clips of his original Japanese voice, then a female English dub from the '90s (which had me completely fooled back in the Toonami days), then once again male for an updated English dub in 2014. Don't miss the irony that the West was censoring homoerotic romance from globally popular anime at one point in time.
By far the most famous instance of that was in S3(94) when the first English dub portrayed these two as "cousins" rather than...y'know.
Then in S5(96) the Japanese showrunners actually made a slight adjustment from the source material. In the manga these three are girls pretending to be boys, but in the anime they're depicted with bare masculine chests at the beach, implying that they transform into girls when assuming their "sailor warrior" forms. The manga author has gone on record as being a bit annoyed about this because her intention was for it to be a "girls only" thing.
Eps. 12&13 of Cowboy Bebop (98) feature the kind of dramatic character you were discussing with u/altmehere (seasoned with a bit of comedy from other background Ts). But do go in for the whole show or none of it at all - it's essential Weeb 101 material. I'll even endorse the dub. Oh and also, the Netflix remake sucks and everyone who truly appreciates the original hates it.
I think I've made my point, even if I stop a decade earlier than you requested. I do recommend this rap battle for some tongue-in-cheek modern "trap" culture (as opposed to WT culture)
You weren't exactly wrong about the T propaganda thing. As you well know the net is infested with them. A huge portion of them have anime avatars, and just like everything else they think anime should be all about them, source culture be damned. But hopefully I've demonstrated that you can tell an honest weeb from an ego-tripping troon by looking for subtlety, nuance, humor, open-mindedness, simple fun, etc...