saringold:

Cuphead Headcanon

Cuphead gets into trouble so much because he’s an adreneline junkie. He loves the thrill of being on the edge, of living dangerously. Gambling scratches that itch, as does danger, pranks, etc. There’s the rush that comes with barely getting away with things that he loves. The alcohol that he fills his head with just makes the buzz burn brighter, and while it is self destructive, he just… doesn’t care. He pursues his next high because it’s fun. It gives him purpose. It’s skirting that line, and he can’t get enough of it. Even if it’ll get him killed someday, at least he’ll go out doing something interesting. The creator himself said in an interview that Cuphead has a deep-seated inability to stay out of trouble, and perhaps that stems from the rush he feels by being in the thick of seemingly impossible situations.

Mugman is genuinely concerned about his brother, though. He sticks close to his brother to save him from himself, because he can’t just… LEAVE his brother to his vices. However, with their debt to the devil, Cuphead actually feels guilty because it compounds the guilt he feels for dragging his brother into his antics in the first place. He never wanted to involve Mugman, but his bro just won’t leave him alone (Not that Cuphead really wants him to, either).

But when this lapse in judgement almost doomed them both, it makes him feel unusually guilty because it involved his most important person, and even getting the greatest adrenaline high in the world isn’t worth the cost of his brother’s life and soul.

(Also, I do think that he is greedy, but his greed is motivated more by the thrill of the possibility of winning/losing than a desire for money. After all, more money = more gambling = more highs)