Re: Fun Home, I lost my father to suicide at around the same age as Alison. I cried through the last 20 minutes of the show, but overall I found Fun Home to be more cathartic than anything. The concept of an adult woman finding whatever peace she could with her father's memory was incredibly powerful.
As for saddest, I'll go with West Side Story. Cabaret is terrifying, but less "sad" IMO since Sally and Cliff are such flawed characters to begin with.
Not a stage musical, but movie. Dancer in the Dark with Bjork. It's simply stunning. One of the best movie musicals I've ever seen. I've only been able to sit through it once, a few years ago. Extremely sad. I keep wanting to watch it again, but have to prepare myself. Lol. I recommend it to everyone who loves musicals, but always with the disclaimer that it will depress the F*** out of you.
SisterGeorge said: ""Carousel." I spend most of the show with a lump in my throat. Part of that, of course, is because the music is impossibly gorgeous."
Except I wouldn't really call it sad. It's an optimistic notion--Billy's redeemed--but, yeah, from the reprise of "If I Loved You" on, how do I know how good the staging is with all those tears in my eyes. Even before that.
Ordinary Days is pretty darn heartbreaking, even though there are certainly light-hearted points. If anyone doesn't know the show, just listen to I'll Be Here right now.