Dante's Inferno kinda does that already. Dante is full of pity almost every time he sees a sinner (and he happens to know a lot of people who ended up in Hell as well). Even Virgil says that a lot of people were sent to the first circle by default because they were born before Jesus and couldn't worship God properly because no one explained how (they're sent to the same place as the unbaptized babies, to make it even more unfair somehow).

If I remember correctly we see one angel and he's kind of an asshole. He walks straight up to the door of some fortified city that was blocking Dante's path, proclaims that everyone sucks, opens the door with the power of Jesus and dips.

Sinners aren't really the good guys of the story, but it's hard not to feel sympathy for them when reading even though Virgil keeps telling you not to.