Harsher in Hindsight: Trevor speaks of Fishbait as a sleeper agent due to his 9/11 views that the West didn't put the Saudis in lawsuits since most of the hijackers were Saudi and he doesn't believe that other religions have extremists. Cue reports of radical Buddhists targeting Muslim minorities in Burma and Sri Lanka in 2017 and 2018.
Michael Nasry, after seeing his brother Omar killed despite being unarmed.
Rip, especially after his divorce.
Bear. At the beginning of season one he is about to become a father. Flash forward a few years and we learn that his daughter Sarah died when she was only a few months old, and he and his wife are having difficulty conceiving another child. And to make things even worse for him, Bear's wife leaves him at the end of season one. Then she gets shot by Chloe and dies at the end of season 2 right when he has decided to try and make up with her.
All of "Six," if you think about it. The women describe what their lives would've been like if they'd never married Henry, and all of them would've been so much happier. (Well, except for maybe Anne of Cleves, who got a pretty sweet deal in the end in reality as well.) In particular, Katherine Howard imagines a world where she told Henry Mannox to piss off, and decided she didn't need him. It's hard not to tear up a little at the realization of how abused this girl was. And throughout the song, the women sing that this concert, in which they've retaken the narrative and spoken for themselves for once, is only going to last "five more minutes." After those five minutes are up, the show is over and we're back in the real world, where most of these women we've gotten to know and care about met tragic ends, and most people simply remember them for how their marriages ended. Ouch.
The final verse of "No Way," in which Catherine of Aragon sincerely tells Henry that if he truly has a good reason for divorcing her, if she's really caused him any pain, she'll accept the annulment and leave with no further hassle. She just wants him to explain a single thing she's done wrong. But, of course, Henry doesn't have a good reason, which just pisses Catherine off even further.
"Heart of Stone," in which Jane Seymour, "the only one he truly loved," makes it clear she is well aware that Henry's love for her would likely evaporate if anything happened to their son. And, tragically, it did, though Jane as well as Henry were long dead by the time Edward passed away at the age of fifteen.
The Woobie: While all of the wives apply to some extent for various reasons, Katherine Howard stands out for having been used by (much) older men for sex since she was thirteen. When she sings about finally finding a friend who doesn't expect sex from her in Thomas Culpeper only to have those hopes dashed away with the realization that he also only sees her as a sex object rather than a person, you just wanna give her a hug.