Basically, Jared Leto won an Oscar for his role playing a transgendered character in Dallas Buyers Club. I haven't seen the movie or read the book myself. I'm not sure I've seen anything with Jared Leto in it, certainly nothing I could place as his work. I really have no stake in whether this particular movie is praised or criticized, and I certainly don't want to defend it against something I suspect, at some level at least, is a valid point. I mean, actors do play characters with roles very different from their RL selves. Irene Bedard, one of my favorite Native American actresses (she's Inuit, if I recall) has played characters from not only a wide variety of Native American peoples but also quite a few Hispanic roles. More personally, I've played a variety of roles in school productions - men, women, tree nymphs, whatever was needed. Being transgendered seems a little different, though. I mean, it's a fairly unique experience I'm not sure people who haven't transitioned can fully relate to.
Still, the blackface connection really bothers me because it seems to skim over why blackface is so objectionable. It's not just that you had a white person playing a black character. Blackface was about a white person playing a farce of a black character, building on some really racist ideas that black people were always happy, always singing and dancing around and generally not having the emotional maturity of white characters.
If you want a parallel, one example that springs to mind is John Travolta's character, Edna Turnblad, in the 2007 remake of Hairspray. You had a cis-male wearing a fat suit and fake breasts, parading around as a woman but as a really bad parody of a transgendered woman. She's not actually described as transgendered (she's just a really masculine woman character), and when I saw the movie I found myself thinking a lot of people might make that connection. Not all of them in a good way. And you may can think of other examples where a certain character is put out there as a walking stereotype of some particular group. The Jack character on "Will & Grace" comes to mind for homosexuality, to give another example. Rocky in Rocky Horror Picture Show is probably an even better example for what we might call trans-face. But you get the point. Blackface wasn't just a problem because it was a white man playing the parrt.
Maybe I'm more bothered by this than a lot of people because I'm Southern. I don't know. I do seem a bit sensitive to these subtle points. And I'm not blind to why people would be bothered by the Jared Leto thing, really. But if the Dallas Buyer's Club is a problem, it's not because it's doing what blackface did back in the day (and, sadly, today). That doesn't make the Jared Leto thing okay; I guess I'm just upset over forgetting there were other things going into why blackface is so wrong.
And yes, I really am a big enough of a geek that that bothered me enough to write out 600 words on this on a Friday night. Don't pretend like that's a surprise. :-)