The Chronological Rory - Part 1: 2008 - 2014

2008

Here’s the world's first Rory! Honestly at this point he has absolutely nothing going for him - his whole concept begins and ends at ‘I think huskies are cool’. His default outfit feels kind of bland, which is funny because it’s not too far off from Syrus’ and clearly I’m fine with his outfit. Additionally, he’s one of my tallest characters (definitely has the longest legs) but routinely wears his jeans rolled up a bit - there’s no real logic there besides that it looks good on him, haha.

While not as bad as some of the others (Eli) I’m still at the point where drawing animal heads looks somewhat awkward - though to be fair I could probably say that about my human drawings at the time as well…

Something I only just now noticed is that he’s wearing the world’s smallest dog tag here.

Version one of this pic! Early on Rory was going to take a slightly more active roll with Syrus, but that ended up changing a bit - especially when Tanner happened. Syrus looks fine here, but Rory’s head came out somehow weirder than last time…

Incidentally, probably the first and last time Syrus looked happy - I’m not sure, I’m not really keeping track...

2009 - 2010

Nothing much to say for the first couple of pics - still just getting used to drawing him a bit. He kept that small dog tag for years though - was it actually even a dog tag? The one noteworthy thing here is I made the top of his hands black (though its hard to notice in the scans) but that’s something I ended up dropping. I feel like the way I drew the fluff on his face in the second pic was the best so far, so naturally I dropped it entirely for full-on anime spikes.

Do you know what else happened in 2010? Summer Wars was released! This pic was loosely based on that movie + Digimon: Our War Game’s aesthetic. But clearly that can’t be the real Sy - he’s far too outgoing and doesn’t use social media much. Be on your guard, Rory!

(And look - he has a proper dog tag!)

2010 is also when Rory and Eli’s friendship was officially established, catapulting Rory into relevance!

2011

Thought this picture had more potential so I tried out a redraw - definitely not perfect but I’m still fond of this version. I lied earlier - this was the last time Syrus was happy. Also the last time Rory ever wore that sweater.

For the most part these two are in their own separate groups now. Do you think they can still be buds in the future?

2012

I’ll be honest, some of my pics of Rory ages particularly unwell,  his face can be kind of off-putting. This is a good example. Is it the eyes? The somewhat human-shaped head? A bit of both, really. I’m trying really hard to figure him out, and I’ll come back to this pose several times to do it.

Apparently the first pic of Eli and Rory I drew (not including their comic, of course)! I thought the idea of Eli standing on Rory’s feet in this kind of impossible way was a fun visual. I start to streamline the fur on Rory’s cheeks, something I’ll continue to refine going forward.

2013

Stock art version 2! This one is much better, more proportionate, and his cheek fur starts to look better here. There’s still just something about those eyes though… where are you even looking, Rory?

Did I ever mention that Rory had a silver fox girlfriend for a while? I ended up cutting her along with a decent chunk of other characters so I could focus on my main six and not spread myself too thin, but I’d like to bring her back someday one way or another. She was my most fashionable character by far. These two were used for this joke since because they were the only ones dating at the time, but looking back this seems way more like a Tanner gag doesn’t it?

2014

This one was based off a meme of two dogs in this exact situation (I’d originally found it with the same caption on the pic as well). The fur on Rory’s cheeks looks dangerously close to hedgehog spines or something, what kind of gel do you use, Rory? 

I stopped drawing the silver fox shortly after this, which is hilarious in the context of the last couple of pictures because it looks like she bailed because Rory was a crappy boyfriend. Don’t let these pics fool you, he’d be a very good boyfriend, I promise you!!

This is one I’d like to revisit in some manner - it’s a fun little character moment with Rory clearly not particularly comfortable as his friends sleep, but he’s putting up with it for their sake. I put a lot of work into this one but ended up not being too happy with the result. I do love Eli’s face though, so it wasn’t a total loss.

His eyes are getting better, at least.

Another pic of these two boyos hanging out! I ended up redrawing and finishing this one, but I’m still really fond of this version and how loose it is.

Part 2 coming soon!