Mortimer from Splitting Image changed SO MUCH. The story is 7-10 years old though, so that's a bit expected. Unfortunately I threw away my oldest painting of him because I didn't have plans to reboot the story at the time.
Mortimer circa 2011 was a pretty boy, white hair, gray Gandalf robes, straight, and basically had a 'oh I'm CURSED WITH THESE AMAZING POWERS no one understands' kind of personality. He was pretty much a carbon copy of anothe OC of mine from another story, which explains why I lost interest with the original draft, but also in general just an undercooked character because I was more enamored with the idea of an ex-villain than what would actually happen inside their mind.
Then when I wanted to make a new art project, I looked into why I liked the characters he was based on - Megamind, Jack Spicer, Presto, Count Bleck. And I noticed that as a teenager I REALLY missed on what made them work.
Mortimer NOW is slightly middle aged(just lacking in facial hair), jet black hair after much palette experimentation, a much more elaborate outfit to show a more prideful but reserved attitude, bi and with actual preferences other than characters the plot demanded, and with a far more developed personality - from his self-loathing, his educated past but bad tendency for self sacrifice, to wanting to depend on other people because he thinks he's no longer allowed to be treated well, the ego that shows when he thinks he can get away with having fun, and big ol' spoiler mental issues.
Design wise, I had a really inspired class where I just captured Mort's new personality perfectly, but it still needed a lot of adjustments because he'd be horrible to redraw and he isn't one to draw attention to himself. I also started human anatomy art classes and the improvement was obvious, to say the least. One detail that's hard to notice is that his eye scar actually is at a 45° angle now rather than going straight down; I have way too many non-comic OCs with samey looking scars.
Sometime last year:
Final comic design: