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(I had not tried to do Inktober before, because I spent most nights in October out doing saw-whet owl banding, so it doesn't usually give me a lot of time for art. In Oct 2017 I decided to try to do it, by setting myself a limited challenge: just simple portraits, mostly in greyscale, each done on a 3x3 post-it note. For many of the days, I managed to do 2 pieces.)

If you are not familiar with Gravity Falls, then you won't know that Shermie Pines is one of the Great Enduring Mysteries even now, after the show has ended. In short: Shermie is the grandfather of Mabel and Dipper Pines, and the brother of Stan and Ford (which is what makes both of them great-uncles.) However, nothing at all is known about Shermie from canon other than that he exists. Is he older or younger than Stan and Ford? Unknown! There is a baby shown in Ma Pines' arms in ATOTS, when Stan and Ford are 17/18; and while the easiest explanation is that that is Shermie, and thus he's a much-younger brother, the timeline actually does not work that well. Therefore, some in the fandom headcanon that he's a much-older brother who was gone from the house during the ATOTS flashbacks (and that the baby in ATOTS is Shermie's son, and Mabel and Dipper's father). Wow, I can't believe I've gotten that good at summarizing that entire controversy, lol!

I’m not fully sure this is where I want to end up, for the older version especially, but it was a start. Headcanons ahoy! So I tend to lean towards the idea that Shermie was a much-older brother who was absent from the Pines household by the time the Stans were about 5 or so. That would make him enough older that he wouldn’t have felt a part of their lives during those formative years, and they would effectively have grown up without an older brother in the house. I considered having him go into the Navy, but decided on the Coast Guard (either branch is tied, for me, to his seacoast-town upbringing) because a friend’s son happens to be in it. It would still have resulted in his going to Vietnam, and is probably also a good reason why he wound up settling on the west coast. (He might have done a tour of duty in Hawaii before ending up in San Diego, and eventually the Bay area. That is, if he lives locally to his son’s family.)
For young Shermie I looked at a bunch of portraits of Coasties from the Vietnam era, to make sure of the uniform. I softened his jaw a bit (though not as much as I meant to), so that he wouldn’t look exactly like the Stans. (Pretty close though, huh.) His glasses are based on Vietnam-era GI issue (they did come in a sort of clear grey color).
Older Shermie owes a LOT to the version by @icefeels , here and here (and from her One Sword series ). I made his hair long enough to accommodate the man-bun, but thought it would be fun to see it down (the famous Pines hair curls!). Still a tough old sailor, but looking a lot more like an old hippie these days.
(Tumblr link .)

Description
(I had not tried to do Inktober before, because I spent most nights in October out doing saw-whet owl banding, so it doesn't usually give me a lot of time for art. In Oct 2017 I decided to try to do it, by setting myself a limited challenge: just simple portraits, mostly in greyscale, each done on a 3x3 post-it note. For many of the days, I managed to do 2 pieces.)

If you are not familiar with Gravity Falls, then you won't know that Shermie Pines is one of the Great Enduring Mysteries even now, after the show has ended. In short: Shermie is the grandfather of Mabel and Dipper Pines, and the brother of Stan and Ford (which is what makes both of them great-uncles.) However, nothing at all is known about Shermie from canon other than that he exists. Is he older or younger than Stan and Ford? Unknown! There is a baby shown in Ma Pines' arms in ATOTS, when Stan and Ford are 17/18; and while the easiest explanation is that that is Shermie, and thus he's a much-younger brother, the timeline actually does not work that well. Therefore, some in the fandom headcanon that he's a much-older brother who was gone from the house during the ATOTS flashbacks (and that the baby in ATOTS is Shermie's son, and Mabel and Dipper's father). Wow, I can't believe I've gotten that good at summarizing that entire controversy, lol!

I’m not fully sure this is where I want to end up, for the older version especially, but it was a start. Headcanons ahoy! So I tend to lean towards the idea that Shermie was a much-older brother who was absent from the Pines household by the time the Stans were about 5 or so. That would make him enough older that he wouldn’t have felt a part of their lives during those formative years, and they would effectively have grown up without an older brother in the house. I considered having him go into the Navy, but decided on the Coast Guard (either branch is tied, for me, to his seacoast-town upbringing) because a friend’s son happens to be in it. It would still have resulted in his going to Vietnam, and is probably also a good reason why he wound up settling on the west coast. (He might have done a tour of duty in Hawaii before ending up in San Diego, and eventually the Bay area. That is, if he lives locally to his son’s family.)
For young Shermie I looked at a bunch of portraits of Coasties from the Vietnam era, to make sure of the uniform. I softened his jaw a bit (though not as much as I meant to), so that he wouldn’t look exactly like the Stans. (Pretty close though, huh.) His glasses are based on Vietnam-era GI issue (they did come in a sort of clear grey color).
Older Shermie owes a LOT to the version by @icefeels , here and here (and from her One Sword series ). I made his hair long enough to accommodate the man-bun, but thought it would be fun to see it down (the famous Pines hair curls!). Still a tough old sailor, but looking a lot more like an old hippie these days.
(Tumblr link .)