All spoilers are unmarked.
- "Something Just Broke", the one truly honest and heartbreaking song in the show, about the everyday aftermath of an assassination.
- Booth's solo in "The Ballad of Booth" qualifies as well, showing off how desperate he is to not be remembered as a madman. At least until he calls the President a "nigger lover," at which point he loses all sympathy.
- Czolgosz's portion of "The Gun Song," where he meditates on all the men who labored in factories or mines and were injured or killed just to make a simple object which in turn will be used to kill more people, all so the bosses in charge of the whole operation can make money off selling it.
- Some lyrics of the "Ballad of Czolgosz" are pretty damn sad, and arguably made more so by the cheery melody.
- Zangara's parts of "How I Saved Roosevelt" emphasize that he doesn't care who he kills because he has nothing in his life to lose.
- "Unworthy of Your Love", which shows how desperate and sad people in Mad Love are.
- The "I'm going to the Lordy" parts of "The Ballad of Guiteau" are quite plaintive, which is jarring compared to the almost-constant sunny optimism of the rest of the song.
- Byck's final "Have It Your Way" monologue, which starts off being about cold hamburgers and ends up being about his Abusive Parents and his feelings of helplessness in the face of government corruption and dishonesty.
- "Another National Anthem" has the assassins go through a group-Villainous Breakdown and (depending on the production) the Balladeer getting cornered and chased off or getting transformed into Lee Harvey Oswald.
- While most of the assassins' Motive Rants have some concrete goal or political ideation, Sara Jane Moore just sadly says, "I did it so my friends would know where I was coming from... I did it so I would know where I was coming from..."
- The Balladeer desperately pleading with the assassins that while killing people won't solve anything, the world isn't as bad as they've made it out to be, and good things happen every day to completely normal people. It doesn't go through.
- When Guiteau runs up to President Garfield and asks to be made ambassador to France. It's the first time the eternally-cheerful and optimistic Guiteau wavers, and he sounds like he's about to cry as he has a moment of clarity - his dream is silly and unattainable, and everyone thinks he's crazy.
- At the end of "November 22, 1963" in the 2004 revival, Lee Harvey Oswald shoots, then turns back to the audience - where his white shirt becomes a projection screen of actual footage of the JFK assassination.
