I have to give (S)heplacements for posting this video:
https://www.youtube.com/watch?v=VbeovM4RCh4
Ted talks in general are wonderful to listen to. A nice short 10-20 minute speech that's very well written, and can be a topic about almost anything (but is always inciteful). It's mostly about how we all dress up as people we aren't really (but are trying to impress others). Also talks about how those of us in the closet are really living a lie. To some degree I agree with that, but the desires vary greatly. There is always a risk / reward to all choices in life. She's really brave at the end, taking off her dress, wig, and makeup on stage.
I also found this gem:
https://www.youtube.com/watch?v=bzj1BTdfoeI
It's similar thinking, but focusing on making drag more fluent and more normal. Specifically, it talks about an event in the UK called "sink in the pink" which is a party for the LGBT group, but it also tries to mix in non LGBT people to get those that are on the fence to cross over (even helping some of them to dress up in drag if they desire).