Inktober! I'm doing it differently. Expect a drawing every few days.
Prompt 1: Oldest OC
Here I've drawn (most) every rendition and major design change for Leon since I created him.
Only missing a few wolf designs that wouldn't fit.

Leon Noir is my oldest OC. He started out as "Lion" (Lee-own) 10 years ago in my pitiful playthrough of A Link to the Past. He was then transferred into my Pokemon White game as my playable character to which his current design has evolved from since. The "wolf" aspect of his I'm 100% convinced derived from Twilight Princess. I have no other way of explaining it. It started in the Pokemon edition, and he was called a "Wolfeon". "Wolfeon" became a normal wolf (not pictured) sometime down the line. It was like this for years. UNTIL Pokemon Sun and Moon came out. And Lycanroc was announced. Immediately I went from "Wolfeon" to having a canon Pokemon to base his wolf design off of. Also the design looked very reminiscent to "Beta Leon" as I call him. t wasn't until last year that I abandoned the Pokemon version entirely and made him his own thing apart from Pokemon. He's was and now continues to be the mentor figure in @sapphydragon's novel series Voices of Legend. And I frickin love him still.
I love seeing characters grow. I hate seeing when people abandon their old characters or sell them off. Looking back and seeing how far Leon has grown and come has been an amazing experience. He's changed so much over the years for the better, and that's what I love about being a story teller.