Ok so first I wish to say, a lot if Broadway has become more accepting of LGBT and Drag/Crossdressing recently. And now for the highlights

First we have Bertie Carvel playing Miss Trunchbull in Matilda

Billy Porter as the Drag Queen Lola in Kinky Boots (a personal favorite musical!)

And lastly, Gregory Haney as La Cienega in Bring It On

So there is the Drag/Crossdresser and Trans roles in Broadway and the Actors Playing them
(Or in Carvel's case the Cisgender role that he is Crossdressing for)

As for Haney, he has stated when asked about how he felt going to the audition for the part that he "in that moment understood the challenges my character would face, and how she would react to those challenges, how she would overcome those challenges, she doesn't know the meaning of failure."