Finally found a picrew that has a decent variety of options for masculine characters! So I made some 1926 OCs mostly to figure out what these guys look like. (Sometimes it takes me a lot of writing to figure out how I think someone looks. Len and Danny look very different from how I imagined them at first.) First up, here's Danny Kilpatrick, WWI veteran and gangster, looking for a career change that maybe involves not having to do any of the things you have to do as a gangster (except maybe cheating on taxes, he could do that), and poor Nicky the bartender, who is tired of angels and demons in his bar at all hours of the day and night.
And then there's Leonard! Leonard is a demon and I don't think I have captured either his eyes or his terrible fashion sense, but this is the best I could do. For maximum Len-ness, please add a fedora. I think in the first scene maybe he had a handlebar mustache but he'd have shaved that off pretty fast once he got to Earth and realized no one else was wearing one.
Next to Len (and wholly unimpressed) is Raphael, who is a. very much not Crowley; b. tired. Very tired. Let him try out sleeping, he probably invented the concept and he's never been allowed to go and see what it's like.
Then I also made two characters from Heaven (who I accidentally ended up shipping), Kaveh, a deceased nephil who got into Heaven and is grumpy about it (although I see him as having oranger eyes), and childcare angel Manakel, who is Doing His Best With What He Has Been Given and doesn't get paid enough for this. (Maybe he doesn't get paid at all? It's not great, Heaven. tbh I'm not sure this is my definite Manakel mental image but it's a start.)