It is a truth universally acknowledged that in most musicals, everyone dies. Theatre evokes human empathy as much if not more than media such as movies or TV shows. Being in the same room as the people performing and their characters living through the extremes of the human condition makes it practically impossible not to experience their pain along with them. Maybe that's why theatre people tend to be so emotionally unbalanced. If you're interested in becoming one of us, these songs are a good place to start.
An entire musical of two enemies turning into friends turning into enemies turning back into friends comes to fruition in this one song. Literally years of emotions are expressed in five minutes. If you know anything about the Wizard of Oz, you know what comes next, and you know it's not a happy ending. Anyone who has ever had a friend will have some feelings during this number.
2. Stay Alive (reprise) - Hamilton
It's one thing listening to this on the soundtrack. The most innocent, naive character in the musical dies, as if by this point, the audience (and of course the main characters) hasn't already been through enough. It's Eliza's reaction at the end of this song when (if) you see it live that absolutely destroys you. In this moment, she's so far from the "Helpless" Eliza we met in Act I; her life has fallen apart. Really, the entire second act is an emotional roller coaster that only goes down.
3. I Am the One (reprise) - Next to Normal
Sad reprises are a big thing in musicals. Much like Eliza in the previous one, this is the moment where Dan's life has fallen apart. After experiencing this song, the words "Hi dad" will carry a whole new meaning for you.
4. A Little Fall of Rain - Les Miserables
There are so many opportunities for tears in Les Mis. Heck, "miserable" is in the title. But this one might take the cake. It is simultaneously an unrequited love song and a death of a favorite character song. Truly the perfect storm, no?
5. I'll Cover You (reprise) - Rent
This one follows the motif of being a sad reprise and a favorite character death song. Besides the death, everything is going wrong for the characters anyway, but this is a moment where they come together as a community to mourn the death of the best character in the whole musical. It's gorgeously tragic.
This is truly the emotional catharsis song of the musical. With all three Alisons in one number, this simultaneously conveys Alison coming to terms with her father's death as well as a feeling of nostalgia. This is the moment where she finally makes peace with her past. And it's so freaking beautiful.
7. The I Love You Song - 25th Annual Putnam County Spelling Bee
You wouldn't expect a musical about a spelling bee to be so emotionally riveting, and at it's core, it is a funny show. That makes this song all the more effective. You're not expecting to cry, but then Olive comes along with her parental neglect and sad, lonely existence. You're lulled into a false sense of security, then BAM! Truly evil, truly masterful.
8. Left Behind - Spring Awakening
This song is interesting because it is about a death, but it's very removed. It's as though he's watching the funeral from afar and speculating upon what the parents of the deceased must be feeling. It's not your usual death of a loved one song, but it's devastating in its own way.