Yeah, I think that they’re probably all still problematic (Boys Don’t Cry is the oldest, I think in the late 90s, Breakfast on Pluto early 2000s, TransAmerica, slightly later). But if that can be a data point in film making that makes people realize that casting trans actors in these roles means that they roles are more resonant with audiences, that’s a great thing. I’ll have to cast around and see if I can find some commentary on these films and how trans audiences received them, if at the time they embraced them for telling trans stories or if they rejected the representations as inauthentic.
OH! I almost forget The Crying Game, with Stephen Rea, with Jaye Davidson (a gay, cis man) playing a trans woman, who was an untried actor in the role:

Another critical acclaimed film, but one that people sort of made fun of, too, if I remember, because of the “big reveal” towards the end. I think it was considered a ground breaking representation at the time, but I don’t know how it would hold up today.