Here are my initial concept sketches for Duff Chudley in my Point and Click Collab world. Duff was actually one of my sister's characters way back in our days of all-but-the-kitchen-sink roleplaying, a teenage helicopter pilot and skateboard enthusiast with a lust for life and not that much going on upstairs. He was known as "The Dude King," the leader of a group of morons that included my characters Ted and Will. They were all very cheerful and enthusiastic, and very athletic, but also SO very dim. Except that over time, it came out that none of them were quite as stupid and "whatever man" chill in isolation as they were together. They just liked to have a good time when they were in a group, and somehow that meant checking their brains at the door.
In the P&C collab, Duff is the very first person Ssam meets upon entering my land/world/whatever. Due to the recent assault by the Unpeople, traffic between the other lands and my particular island has all but evaporated; somehow, the risk of having one's memories and identity stolen away is not so great for tourism. Since Duff's job is to pilot the dirigible that takes people from the mainland to the island, business has been lacking lately. Even worse, the situation being what it is, nobody has come to relieve him from his shift in weeks. As such, when Ssam encounters Duff, he's sprawled out in his little outpost, snoring up a storm. Once Ssam manages to wake him up, Duff is so thrilled to have a customer that he offers to ferry Ssam across to the island free of charge and to wait for him at the loading docks, so long as he's not attacked, in which case Ssam is just out of luck. He does extend the request that Ssam keep an eye out for his fellow dudes (and overdue shift reliefs) Wil and Tedd, because their absence has him a bit concerned, all things considered. In fact, when he says he'll take you back whenever you want, he's only being half-honest. If you come back without news of Wil and Tedd, he begs and pleads you to try asking around again, please, as a favor, since he was so nice to fly you over for free and all? Of course, you can always lie to him, and he'll take you back, but he's surprisingly savvy to dishonesty, and will then force you to pay him every time he flies you anywhere. Honesty is the best policy, folks.
These have absolutely nothing to do with the P&C Collab, I just decided that I don't have enough characters with glasses, so I sketched the ones I have. From left to right, top row first: Ghost Story's Matthew, Tabula Rasa's Fara Meloy, and a currently unnamed character from TR. Bottom row: Another unnamed character (I'm thinking of Andy or Jeremiah right now, but I'm still pondering) from TR who Fara knew as a teenager and young adult, Teenage!Fara herself, and Brian from Renerra. I have a thing for spectacles, so I have no idea why so few of my characters wear them.
As a side note, I'm really fond of Fara and Matthew as characters at the moment, and slightly sad that the wonderfully and blithely sarcastic Andy/Jeremiah/Whatever has such a small role in TR. Actually, I'm not sure he's in TR at all, and only in the theoretical follow up story to a minimal degree. He exists primarily in backstory.