Probably Going Clear, which was an excellent documentary but incredibly hard to watch due to the content. Man I fucking hate Scientology.
Emotionally difficult doesn't make it a bad documentary, in fact when truthful the best ones are really distressing, because they cover things that no one wants to talk about. I wouldn't say "Going Clear" is the worst on that. Some trans issues ones are just freaking heart breaking.
Damnit Kyuubi I was trying to stealth plug Going Clear! I feel like a lot of people treat Scientology as some sort of weird cult instead of the malicious force that it is, breaking up families, physically and mentally abusing it's members, putting young men and women in extremely coercive situations.
And yeah there are some really heartbreaking and infuriating ones out there on trans issues. I remember one I saw about trans women in men's prison that was pretty hard to watch, I can't imagine what it'd be like if I had a more intimate connection to the issues. I'm a survivor of sexual assault so I could empathize with that aspect of it but there was just so much more you know? Things I wouldn't have even considered, I guess I don't really have to tell you though huh?