I've been chronicling the adventures of Destructor and The Mob since I was in third grade. I've done this in a variety of different ways: Prose stories and histories, long lists of characters, playing "Mob" with my siblings and the neighborhood kids or just by myself, or even simply mentally advancing the storyline by increments as I drift off to sleep. Nowadays of course there are also the comics I've done with the great Matt Wiegle. But the main record of Destructor's world that I've kept over the years is in the form of hundreds and hundreds of drawings of the characters, from the waist up, mugshot-style. I drew these all through elementary school, middle school, and high school, mostly in giant three-tiered sheets of computer paper, the kind that had little holes on the edges. I've got a blue binder full of these things--if you're ever at my house, I'll show 'em to you.
So here are the three drawings I have of Destructor from that period.
This is the earliest extant drawing of Destructor, but it's not the first one I did. I first drew Destructor and a lot of other characters in third grade, but lost all the drawings on a class trip. I redrew him...I'm not sure when, exactly. Several months later, maybe the next school year? So that would date this drawing to around 1987, most likely. Note the spikes and horns, always a very prominent part of how I saw the character. You'll probably be seeing them down the line.
As I got older and "better" at drawing, I started redoing some of the most important characters so that they'd look as cool as I was capable of making them look at the time. I'd imagine this drawing was done in middle school, so around '90-'91, something like that. More spikes, bigger horns.
In high school, I finally bit the bullet and broke the mugshot format, and started drawing legs and feet. I did this in a series of full-body pin-ups on loose leaf, no doubt inspired by the pin-ups in the comics I'd finally started reading by this time. This probably was done in 1995. None more spiky!