I thought about this for a while and then came to the conclusion that really, honestly, it had to be this guy.
Art shamelessly sampled from Askgarysmith.
Here’s why in as few words as possible.
Great antagonist to Jimmy – he’s subversive where Jimmy is direct, he’s cunning where Jimmy’s blunt, and he’s totally chaotic; he messes things up just to prove that he can.
But here’s where it gets into it, because aside from being nasty, bullying, manipulative, power-mad and generally messed up all across the board, Gary is just a 15yr old teenage boy acting out. If you get underneath his actions there’s really just a screwed-up teenager who is probably more insecure than he wants to give out, and who feels like he can’t trust anyone (that no matter what Jimmy says he’d have betrayed him in the end).
I love that you don’t see enough of him in the game to satisfy the player, and I love how we never really get close enough to him to reveal anything honest – it’s all talk, because he’s all talk. Gary as we see him in the game is really just the tip of the iceberg, and that’s what makes him so fascinating to write and explore as a character. There is somuch we don’t see.
I love my antagonists with scales of grey, and the thing about Gary is that he’s a villain, but he’s an incredibly human one, and he can be very easily misunderstood by the people around him. This isn’t to say he’s actually a nice boy and he’s misunderstood – he’s a nasty boy, but that doesn’t make him any less misunderstood. Villains have their reasons for behaving the way they do as much as heroes do, and they’re rarely born from a classically ‘evil’ origins.
I just think there’s so much depth to him, and he is often treated as a 'black box’ of a character where he just acts without showing his process. But once you get into his head, it’s suddenly very hard to get back out. As I’ve found out
I’d marry Eunice, because once her very limited vocabulary ran out, I’d never have to speak to her again. I’d sleep with Beatrice because she has the most tolerable hygiene levels out of all of them. I’d go on a cruise with Edna so that I didn’t have to touch her, and maybe she’d cook and poison all the guests. That’d at least be entertaining.
((So last week, when I was gone for an impromptu vacation, I asked people to submit some suggestions for art so that I could make up the lost time. The suggestion I got most often was Gary/Jimmy, so here that is - be sure to look at the hi-res version; it’s big: