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I suppoye that Stalin vs Martian would make Stalin sympathic, even if just through parody.

Pirate ganes usually make abject murderers look cool.

War games occasionally raise such issues. And political campaigns sometimes use little games glorifying the candidate (who may or may not be a real life villain).

And history-based games often offer dubious, reductive interpretations of history, which historians may argue misrepresents the protagonists (the Assassin' Creed series, for instance).

And then you have strategy games with historical figures, like the Civ series. Or even Total War, often glorifying (already popular) mass murderers ("conquerors").

I meant, they often use historical characters (Teach, Morgan, etc), who easily end up quite glamourized.

Speaking of which, it wouldn't surprise me if it also happened with dubious Old West figures aswell (Earp, Bonney, etc), but I don't really have exemples in mind. Well, there's Custer, but I'm not sure how cool he's supposed to look in 's revenge.

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Lionheart : Legacy of the Crusader, which is a little-known Blackisle RPG with a SPECIAL system that's set in the (altered) times of the Spanish Inqusition does this when describing any figure it depicts that existed in reality. But its an alt-timeline game and that's what they do.

Also, not that he doesn't have any villainous characteristics, but I'm sure that game where you save Trump garners at least a bit of sympathy him despite being satire.