"Hey little guy, it's O.K. if you have to cry!"
—Weepy, Death screen
Personality: Weepy is shown to cry uncontrollably while fighting Cuphead and Mugman, which means he is either really scared, or just really upset. He might not be even trying to hurt the brothers at all, considering that he only cries, but doesn't intentionally hurt them.
Weepy spawns in the middle of the area. Unlike Psycarrot, players can inadvertently be damaged if they touch him.
Weepy's only attack is to cry out water streams on both sides, which rain down tears randomly across the area. Some of those tears can be parried.
- Weepy's name and appearance is reference to the fact that onions cause people to cry uncontrollably.
- He's the only boss that is a pacifist, and also one of the only two bosses that does not outright mock the protagonists or talk about their own strengths or egos in a game over. The other boss being Grim Matchstick.
- He doesn't appear on the Simple difficulty.
- Weepy seems to have similarities to Jerome "Curly" Howard of the Three Stooges mostly because of how childlike Weepy is.