5. Bruce Jenner
This may be cheating a bit, because Jenner has completed the gender transition process and now identifies as a woman. But back in the day when Caitlyn was still ‘Bruce,’ things were rough. It was clear that Bruce Jenner was completely befuddled by his family, especially his wife Kris, who over the years has become less a human being and more an instrument of material will, able to bend everyone to her desires. Bruce Jenner likely kept his need to be a woman secret for so long because Kris knew it would affect the Kardashian brand. So Bruce toiled at the family business, smiling and going along with the silliness, but dying more each day until he finally declared independence…and then said, ‘Call me Caitlyn.’ And showing that her ruin and corruption were permanent, Caitlyn Jenner made sure she charged Vanity Fair millions to tell her coming out story, then wrangled a reality show out of E!