james charles - drag

Although he does tons of makeup tutorials (some with wig and female attire), this is the first video I was truly impressed at what a dramatic transformation he went through (he even comments at the end about how he feels like a woman)
https://www.youtube.com/watch?v=LuAatHCEqUU

ANNA CLENDENING - BEND & BREAK

I stumbled on this artist by searching for "girl music" playlists on youtube.  It has a very positive and uplifting message, saying it's ok if you bend or break.  It also just happens to have a bunch of LGBT people in the video.  I searched through her youtube feed and apparently she came out as lesbian.  Anway, it's a great catchy song and a great music video to match:
https://www.youtube.com/watch?v=Q7IUuMJ5qYU