- Ollie Bulb is shown to cry uncontrollably while fighting Cuphead and Mugman, which means he is either really scared or just really upset. He might not even be trying to hurt the brothers at all, considering that he only cries, but doesn't try to attack them. As of the Switch version's release, it's entirely possible to skip him outright by refusing to attack him.
- The sad, depressing credits music that plays as a Lonely Piano Piece accompanied by a snare drum in the bad ending in which you chose to hand over the Soul Contracts to the Devil and rule over the entire Inkwell Isles that are literally going to hell? It's called, appropriately, "The End".
- One theory suggests that Dr. Kahl's absence from the party in the Good Ending has a rather depressing reason behind it he's lost his finest creation, one that was advanced enough to not only gain sentience, but effectively become a living creature thanks to the soul it held.
- Introduced following the Switch version's release, battle Sally Stageplay and stand on both cherubs on the sides until they stop moving during the first phase. Her fiancé will be crushed to death with the chandelier, and she will cut the first phase short to rush to his side and cry. In the next phase, instead of standing in front of a happy home full of babies, she's in front of a convent, where irate nuns throw their rulers at you.
- YMMV on this one, but the devil breaking down in tears at the end of his boss fight. He looks so depressed afterwards, and surrenders without complaint...
Tear Jerker / Cuphead