It’s hard to really gauge who is the Oldest Oldest because Jesse’s been around for over a decade technically but is unrecognizable in his current form compared to his oldest. It’s sort of a ship of Theseus situation, you feel me? How much can it change before it’s not the original thing

If I had to answer, I’d say Donnie. He’s probably the one who is most consistent with his oldest iteration from 2014, and I’d consider his whole arc in that regard to be one singular character.

His character concept was initially that he was a burned-out former children’s hospital volunteer magician, who accidentally gained ACTUAL magic powers and found himself traveling through dimensions. He was mentally ill and could use his mental state to manifest different magic powers that’d assist him in his travels/in goofy cartoony battles. I was a literal child when I made him so forgive that the concept is Like That

Nowadays he’s an anxious med school dropout who dropped out because of chronic health issues, so he could focus on his musical passions and reach stardom before his health prevented him from it.

His personality is pretty overall similar to his earliest form, just a bit less edgy compared to my teenage sensibilities