Sherman "Shermie" Pines, It Took Me Far Too Long To Make You A Proper Full Body Pic. I First Had Doodled

Sherman "Shermie" Pines, it took me far too long to make you a proper full body pic. I first had doodled him up in late.. 2016? I believe and he's been a favorite of mine for awhile. Who would have thought I would like a character that's never been seen mentioned like.. Five? Times. And take me nearly a decade to give him a mustache.
Anyway this is my Sherman, the eldest of the Pines boys. War Vet, divorced, and loving Grandpa regardless.
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More Posts from Kassiaactuallydraws
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It just occured to me that Stan technically canonically liked to draw, so here's my take of what Stanley's sketchbook would have looked like had he never gave up on art :]

Stanley first found this sketchbook left behind in a dumpster next to a library. The rings that once held the pages together were broken and warped, so he instead fashioned himself a jury rigged binder by weaveing one of his shoelaces through the holes in the side. In the end, it was essentially just a stack of barely held together paper, but he was still satisfied with it.
Pencils were easy enough to snag from the store since they fit so easily inside his pockets; but he had to settle for the shitty stubby pink erasers that barely did its job on the end of the pencils if he made any mistakes.
Stanley wasn't much of a poetic guy, and he didn't do the kind of art that had deep symbolism or meaning behind them. He was more the kind of artist that just drew what was in front of him, plain and simple. Had he been younger, he might have been able to fill in this cobbled together sketchbook in a matter of days, page after page filled to the brim with creatures and adventures of the wildest dreams.
Well, Stanley wasn't exactly a sprightly young child anymore with a boundless imagination to take inspiration from, but 10 years was a long time to be on the road and moving around, so there was plenty for him to draw.
![[Summer of 1971, Kentucky- Natasha Jones. Stanley met her at a small farmers market located in a somehow even smaller backwater town. His fingers were itching for something to distract themselves with from the dull inactivity of the town, and he found his eyes drawn to Natasha lounging behind her fruit stand just across from him. Her body language was languid and loose, like a cat. She hadn't appreciated it when she caught him staring, but was apologetic when she realized she gave Stanley a black eye not for being a pervert, but for simply drawing her. She and him still keeps in contact to this day.]](https://64.media.tumblr.com/69134ecf59bfb42d270ef38873aac07d/7cd7adcd505f3026-aa/s500x750/b81c441970be6612abc1f55496bb1585da9b8330.png)
![[1972- Carla McCorkle. Stanley crossed paths with her completely out of the blue at the Juke Joint. During a brief pause in their dancing escapade, Stanley managed to roughly capture Carla's dancing in his sketchbook. He was enraptured by her boundless energy, and wanted to challenge himself to try and imitate her lively movements and poses on paper.]](https://64.media.tumblr.com/b4f60aabc5c4efb4e745675e9bc6534f/7cd7adcd505f3026-a6/s500x750/f1e8b7b74103735b3b09b3b67d68ac99c287d7f4.png)
(My primary goal was just to make these pages look as realistic as possible, but I did add in mini backstories in each of the pages' image description, if you feel like reading that :])
![[1973- Jack Andersen. Jack was a travelling business man who was staying in room #26 at the same motel Stanley was temporarily residing. Stan doesn't remember what it had been about Jack that intrigued him so much at the time. It might have been his voice, or his height, or his face. In any case, Jack noticed him hunched over the counter and scribbling a portrait of him onto a scrap piece of cardboard from across the lobby. He offered to meet up later to give Stanley a better view of what he was drawing. Stan still has his phone number.]](https://64.media.tumblr.com/348ff999e6f56b3b54fed6e16d14b0ce/7cd7adcd505f3026-1b/s500x750/05d525bfa97ca81403feb0320aa9c48515777468.png)
![[1973- Maddison. She was the waitress attending to Stanley at the diner he had taken a pit-stop at to evade the pouring autumn rain. She had the bluest eyes he'd ever seen, and she seemed delighted when he showed her the small portrait he had done of her in cheap blue ink on the receipt.]](https://64.media.tumblr.com/2bd36e7e2c26f55bcb0db2e0ccde8865/7cd7adcd505f3026-3d/s500x750/3f751d8a01f8e5d2da713eed82f000444d00072a.png)
![[1974- Jimmy Snakes. For such a laid-back man, Stanley never seemed to be able to catch him staying still long enough to draw him. He didn't get the chance to draw him a whole lot.]](https://64.media.tumblr.com/a0995f71a145946a9cb78d42671565ed/7cd7adcd505f3026-e8/s500x750/57b0cfb38606b1724bb06a6d14b56ecc52213010.png)
![[Winter of 1974- Sarah Campbell. Stanley met her out on the streets begging for money with an empty coffee cup. It was cold enough to see your breath fog, and she looked far too young to be homeless already, but she had one of the sunniest smiles that Stan had ever seen on another person. He was dragged into keeping her company when she noticed his sketchbook in his pocket and practically demanded that he draw her. He indulged her, and let her hijack the sketchbook to doodle her own drawings onto the page. She left to beg in a different area after about an hour, and Stan never saw her again. He still thinks about her sometimes. She reminds him so much of Mabel.]](https://64.media.tumblr.com/55c17e78fe05d25643f92fc966891f2e/7cd7adcd505f3026-09/s500x750/48c71dbc2c1aa72e8a98c1327581da153e4d2f47.png)
![[June 1975- Morrison. They met at a seedy bar in a random town that Stan doesn't care to remember the name of. In the afterglow of their one night stand, Morrison asked for Stanley to draw him after learning of the latter's hobby. He remembers Morrison walking out on him with a huff when he saw that Stanley never once drew his face.]](https://64.media.tumblr.com/c523ad68e3bef47801d93e9cc5036c67/7cd7adcd505f3026-06/s500x750/94565141d6bee440bb709097c73fe11cdeb73602.png)
![[He doesn't remember drawing this one.]](https://64.media.tumblr.com/d6ebed0f18d8bbe25c8eca10597433e7/7cd7adcd505f3026-ef/s500x750/55c6c35f4fb3138c99cce763c54b8a28faf75672.png)
![[1976, Colombia- Ana María. She was one of the muscles involved in a cartel mission that Stanley was participating in. His boss didn't notice him sitting in the corner with his sketchbook balanced on his knees during the meeting, and Ana María certainly didn't seem to care, although she definitely noticed him.]](https://64.media.tumblr.com/2847c52820543455c6345facc1ecc1df/7cd7adcd505f3026-c8/s500x750/b8cc0f766f35afa5d930e748c8c8d4f98dce4f07.png)
![[1980, Colombia- Stanley only barely managed to hide his sketchbook from the guards during the initial body search, and he never dared to pull it out in front of his inmates, lest they damage it. Besides, pencils that weren't being used as a stabbing weapon was a rarity in prison, and paper was bound to get ruined with blood at some point or another]](https://64.media.tumblr.com/a3b0b854e8ada0ab970528ac185f449f/7cd7adcd505f3026-50/s500x750/4daccad164f0f85e41bfbfd17e7c4666720a17d9.png)
![[Summer of 2012- Mabel and Dipper Pines. Stan remembered the day he first met the twins; not in Gravity Falls, but at Piedmont, California, almost a decade ago. They had been so small at the time, and Stan had been having such a hard time stifling his tears that he was barely able to hold his pencil properly to draw the slumbering pair, cocooned in their tiny blankets. The extra sixth finger on his gloves hadn't helped with his shakiness, but he was desperate to busy his hands so Shermie didn't notice him crying. He did anyways, and Shermie himself had looked like he was about to burst out laughing at the sight of Stan, the traitor.]](https://64.media.tumblr.com/265cd813e2847aa0c8af43425d9eece1/7cd7adcd505f3026-4b/s500x750/14ee598b9c18d0857e8e03e49919507186955a3b.png)