- Lucy's song "A New Life" is pretty depressing enough as it is, much more so when you know what's about to happen afterwards. In one production the Spider took the letter from Lucy and called her a whore directly before the song (which began with her sobbing).
- Pre-Broadway, Simon Stride stole Jekyll's letter to Lucy and planted it for Lisa to find after the wedding.
- Later productions have "Lost in the Darkness", where Jekyll is visiting his catatonic father in a madhouse and promises to find a cure, wishing him goodnight in a tender voice at the end.
- "Once Upon a Dream," where Lisa/Emma feels she's losing Jekyll and doesn't understand why, but still loves him despite her fading hope.
- "This Is the Moment," while uplifting, becomes crushingly sad in-context since it takes place just before Jekyll first drinks the potion to turn into Hyde.
- "His Work and Nothing More" is an ensemble song as Utterson and Sir Danvers are gravely worried for Jekyll's livelihood, Emma forgives his behavior, and Jekyll himself is terrified of Hyde but wonders if his work is all that matters to him.
- "In His Eyes," sung just after "Reflections" in some versions, details Emma and Lucy both singing about their love for Jekyll and how everything they need in his eyes... when neither of them knows about Hyde, the murders he committed, or that Jekyll and Hyde are the same person.
- "No One Must Ever Know/The Way Back" has Jekyll vow to gain control of Hyde lest his work and name be ruined, culminating in a hopeful creed to rekindle the passion that originally drove him. While sad enough on its own, it's worse with the ending in mind, as nothing stops Hyde except Jekyll's death.
- "The Girls of the Night" details Nellie showing Lucy the reality of their lives, while Lucy is still hopeful for a way out. Some productions move it near the start of Lucy's introduction, making her arc even sadder.Lucy: I have my hopes...
Nellie: I have a child, and children must be fed. Forget your hopes, or you will be misled. With the dawn they disappear...
Lucy: Then why am I still here?
- Nellie's fate. She has no dreams and no hope for a future, but she sells her body for the good of her child.
- One song usually cut from the show is a reprise of "Once Upon a Dream," sung by Jekyll after Hyde kills Lucy.
- The very beginning of "Confrontation," which either reprises "Lost in the Darkness" or "No One Must Ever Know." The former has Jekyll agonize over Lucy's death and his own dire fate, while the latter has Jekyll muse on how the crimes Hyde committed will forever shadow him, whether he's a good man or a madman, and how there's a fine line between good and bad.
- The finale, which takes place either as Emma and Jekyll are about to be married or as they dance at the reception. It ends when Jekyll is either shot by his best friend or impales himself on said friend's sword-cane to stop himself from killing Emma at their wedding.
- Emma's entire situation is depressing, as she feels she can only be herself and free when with Jekyll, who has a double life she doesn't know about at all. It's even worse in versions where Simon tries to dissuade her against marrying Jekyll, but she refuses—her father and everyone else treats her like a girl, Henry makes her happy, and choosing who to marry is the one freedom she insisted upon.
Tear Jerker / Jekyll & Hyde