Cuphead

' Note: This is for information pertaining to Cuphead in the Bad Ending. Therefore information pertaining to Cuphead in the Bad Ending should be implemented onto here and not the Good Ending. '

Cuphead is one of the main two protagonists turned main overarching secondary antagonists (alongside MugMan).

He was once a gambler who bet on the Devil subsequently causing him and his brother's soul due to his greedy actions. In a huge plea-deal who got a chance to get through a series of gathering contract from others who The Devil warrants souls out of making a deal to get those Soul Contracts to pay up the debt Cuphead and Mugman owes to The Devil. Cuphead gives the Soul Contracts and has the option to work with The Devil and give his Soul to the Devil.

Debated Validations

 * Cuphead and MugMan had worked his way towards getting the Soul Contracts to the Devil. However, those were Soul Contracts of their other enemies lives they were in fact putting in jeapordy which doesn't make what they did as heroic considering they would be apprentices of the villain [i.e. King Dice and The Devil] and add the Bad Ending in the game.
 * It can be argued that Cuphead (alongside his brother) were or even are brainwashed/posessed and may have not wanted to fall down into villainy on their own. Thus lacking a moral agency at this point. Including the lack of directly done crimes that most villains need like what The Devil does. However, it remains unlikely considering how Cuphead chose "YES" in working with The Devil to do the same types of crimes together, and given how Cuphead and his brother are seen visably laughing seems to make it less arguable.
 * Considering Cuphead and his brother's crimes range from just vigilantism all the way to conspiracy. Their crimes wouldn't be severe enough to consider them a villain. Although, then choosing to work with The Devil's bidding and then seen visably laughing remains debatable if their crimes later on will remain petty or minor or be thanks become much more heinous. Proving that their once heroical aspects would fall down into villainy as the Bad Ending would therefore prove. Yet, the cliffhanger of them laughing and seeming to be posessed remains somewhat debatable.

What made him heroic?

 * He had tried to get the soul contracts from those who owed their soul to the Devil in order to pay the debt he and MugMan owed to The Devil.

What made him villainous?

 * One thing is for certain is the Bad Ending (in contrast to the Good Ending where Cuphead fights The Devil and saves everyone and choose to be good) he chooses to work with The Devil and becomes evil as he and his brother laughs as the Devil laughs. Presumably (at least in this Ending and alternate universe/continuity) choosing villainy and subverting away from heroism losing away their honorable traits they once had.

Trivia

 * He is one of the few characters who qualifies as Inconsistently Admirable for his Good Ending alongside MugMan. However, he wouldn't be admirable for the Bad Ending.
 * His Netflix Counterpart in the show of the same name is of the making. And it could remain under debate whether or not he falls down into villainy like his mainstream video game counterpart on the Bad Ending or not. Considering how the Netflix Cartoon Spin-Off may be an alternate continuity loosely based upon the game and franchise overall may either be possible or unlikely depending on what the spin-off presents.