- Captain Brineybeard made his terrible deal with the Devil. His ship, enraged that you've come this far to claim his contract, fights on his behalf - Sure, the Captain's launched into the distance, but he survives while his ship continues the battle for him. This happens as well with Dr. Kahl, except he's not the one who made the deal, his giant robot was. So the mad scientist is fighting for his mechanical creation's sake.
- What do the two boys do once the Devil is beaten? Why, burn all the bosses' contracts, of course, therefore freeing them all from their debts. And all the bosses don't hold any grudges against them and praise them as heroes.
- In just two weeks after release, the game already sold over one million copies. As a thank you gesture, the game devs made a drawing with Cuphead, Mugman, Elder Kettle, King Dice, and even The Devil thanking the players.
- Another meta-example is that when Cuphead was announced as the winner for Best Art Direction at The Game Awards 2017, the Moldenhauer brothers arrived to shake hands with Guillermo del Toro and Hideo Kojima before delivering a speech that is both Funny and Heartwarming.
- The same happened when the game was announced as the winner for the Best Debut Indie Game award, but this time, the Moldenhauer brothers brought along their entire family for the award. Once again, Chad delivered a heartfelt speech thanking the staff at Microsoft and everyone for their help into making the game, after which Jared added a hint about buying indie games, which is a bit of a Funny Moment in itself.
- The fact that the majority of Cuphead was the Moldenhauer brothers paying homage to the style of cartoons and video games they grew up loving, because they genuinely had fond memories for them, is simply beautiful, especially when viewed from their perspective - surely you have at least one specific thing you love that inspires you?
- According to an interview with Studio MDHR, Microsoft approached them about bringing the game to the Nintendo Switch. Usually, it's the other way around.
- Ollie Bulb is the one member of the Root Pack who will not directly attack you even as you pepper him with bullets; almost makes you want to spare him, huh? Turns out that if you hold your fire in the latest update, he blushes and smiles at you as he sinks into the ground without a fight. The radish that follows, however, is far less friendly.
- Sally Stageplay really shows how much she cares about her husband, crying for him after you crush him to death with the chandelier in the first phase of her fight, she even stops the fight to do so. Fortunately, in the third phase, he's back as Bacchus, nodding and smiling as she does her best to smite you.
Heartwarming / Cuphead