I really admire Ramona Xavier AKA Vektroid/Macintosh Plus. She pioneered vaporwave and just does great music. I also think its cool how wide-reaching an influence she's had. Usually the audience for a trans artist is limited, but by the nature of her style a lot of people probably don't even know her gender let alone that she's trans.
I also think Jayne County is really cool. She did early punk music, a lot of it about gender and sexuality, and was a huge influence on glam rock.
um and Breakfast On Pluto is actually pretty decent even though it is yet another film where a cis man plays a trans girl. I really enjoyed Cillian Murphy's performance.
and I like that Against Me! album too. I saw them last year actually. My friends and I had sort of followed them for a while, but I became a lot more interested when Laura Jane came out.
oh and also "Candy Says" is a beautiful song about gender dysphoria by my favorite band, The Velvet Underground. if anyone doesn't already know of them, I think they're really worth checking out in general (one of the first punk bands, super psychedelic), but they might be of particular interest to people on here because Lou Reed was one of the first songwriters to write about transsexuals with any humanity. I personally think he did a great job too for the most part.