Well. After my computer blue-screened because I was drawing too many gay men, I had to redraw this all again with worse quality in an old sketchbook of mine from high school. But hey, at least it's something to show for all that work gone.
I give to you, my head canons for some of the listener characters in the videos by @clutzclown
COWBOY - AKA: Evan Reese Mann
Yes he's a kinda generic guy but that's the point. He is the quintessential blank slate. The Everyman. Just like his name is supposed to be a riff on.
DOLLFACE - AKA: Alex Hartford
I needed to give this guy a better outfit than Evan, at least while he's at work he does. When he's at home I imagine Alex only exists in the bare minimum clothing just to try and relax in the rare instances he can. Of course I had to include the maid dress Gideon gave him too. I gave him the name of Hartford specifically so the ship name between him and Gideon would be called "Glass-Hart" because I like how it sounds.
And finally for this go around, we have
CHECKERS - AKA: Kurt Kingley
I'm going to be so real, out of all the characters, Checkers or Kurt as I want to call him, is by far the coolest listener of the group. While nothing he does is insanely impressive, he's just got the most exciting and... Well with his habits I wouldn't call it the healthiest lifestyle but definitely has healthier relationships than a certain Doll-Faced assistant.
Oh yeah, and my other head canon names are these. I'd draw the rest out but I kinda want to wait to get my computer up and running before I draw up any more designs.
Arthur's New Hire - Leonidas "Nidas" Laven
Given the idea of taking this line at face value: "that's not a name I've heard before" I wanted to give Nidas here a slightly more unique name. Also yeah when I draw him he will be a femboy.
I didn't give him a last name because I cannot imagine that he would want to admit he's at all related to his father. I'm imagining he's thin as a rail, nervous all the time, but he is definitely a golden retriever boyfriend.
Wendigo victim - Chris Winters
This name is just a reference to Resident Evil. It felt fitting for some reason.