some doodles of the Pie kids, mooooostly focused on Jam Sandwich
1.) HMMM BITCH BETTER HAVE MY MONEY
Cheese Sandwich and his fav lil stinker
2.) "Oh..........um, okay, sweetie. Ciao......"
The older Jam gets, the better she gets at business and scamming, which means she spends less and less time at home, to the detriment of Mama Pinkie Pie. One of her many "associates" is the charming Gladmane, who despite his kindly, paternalistic demeanor, is absolutely ruthless in his business dealings, and involved with no small amount of seedy underground crime. He's a
dangerous pony to have as an enemy, which is why Jam's taken him on as a friend. They first bonded in their shared disgust of Filthy Rich.
Jam cannot stand Filthy Rich. The dude touts himself as some self-made millionaire, but in actuality, he inherited both a sizable fortune AND Barnyard Bargains from his father. She can't stand his hokey, good ol' country boy act, she KNOWS he's ruthless behind the scenes, and that he's your typical robber baron capitalist. He underpays his workers to mass produce cheap goods, all so he and his stupid chain of stores can pop up and choke out local small businesses. Pinkie Pie and Cheese took a small loan from the Cakes to set up their own party supply/joke shop, and they nearly went under several times because Filthy kept undercutting their prices. He says there's nothing wrong with a little friendly competition, Jam disagrees. She called on Gladmane, and together they strong-armed Rich into staying OUT of Pie territory. Gladmane may be of similar fake-nice cloth as Filthy, but he's more transparent in a lot of ways, and Jam appreciates that. Gladmane, comparatively, is pretty fond of his apprentice, and considers her something like a daughter........uh, nevermind his actual daughter.
Unlike Gladmane, however, Jam does have some standards in which ponies she targets for her con jobs (typically wealthy aristocrats) and very much considers herself a modern day Robin Hoof. No clue why Pinkie's always so gloomy to see her go....
3.) So PB and Jam are fraternal twins and also best friends. Many people, upon entering their teen years, start distancing themselves away from their parents and siblings......it's just part of growing up. These two though? Nah. Never. They're still as close as they were back when they still shared a one-bedroom apartment in Mama Ponka's stomach. They finish each others' sentences and swap outfits on the regular. Jam (much like Cupcake, and also Pinkie), loves PB, and will destroy anybody that so much as makes her baby brother sniffle (yes, baby brother, she's a whole two minutes older than him, so there!) For this reason, she keeps him out of her shadier business dealings, pretending to be a traveling vacuum cleaner salesmare, or something like that. PB is the more dependent of the pair and much prefers to let his sister take charge of situations. When they were younger, PB suffered from persistent shyness and selective mutism, so Jam grew to do most of the talking for him. This isn't always a good thing, PB really wishes him family wouldn't coddle him so much
Since PB's middle name is James (Jam's is Jessie, naturally), she calls him "Jim".
4.) "I'm here to bake scones, or break bones. Your choice, baby brother."
"You don't scare me, sis. Face it. Your cupcakes are dry, and you're gonna die."
Competitiveness comes naturally to all three Pie children, including Cupcake. Especially Cupcake. They all get it from their mom and dad, whose first instinct upon meeting was to try to destroy each other in a Goof-Off. Cupcake normally adores PB, she's adored him from the moment she held him in her little arms and gazed into his baby blue eyes. She'd die for him, she'd (almost certainly) kill for him......but all that goes out the window for the annual Great Canterlot Bake-Off. The greatest baking competition in all of Equestria. PB is her darling baby brother, but he's also a fellow competitor, and sadly that means Cupcake has to destroy him. She will also destroy Missus Cake. And possibly her own mother. Blood and bonds mean nothing in the quest for total baking supremacy. Cupcake. Will not. Be. Stopped.
PB is a little intimidated, but also kinda amused that his big sis is finally taking him seriously as a rival, apparently enough to unwittingly trigger her hyper-manic and volatile Party Mode. Not scared of lil ol' Peebles, are ya Cuppy? His Triple Tier Strawberry Sponge won a blue ribbon in Ponyville just two months ago. Golly, can't imagine why that'd be threatening.....
(I like to imagine the Bake-Off is mostly populated by sweet old grandmas and doddering gentleman, all looking on in confusion and terror as Cupcake and PB try to kill each other)
more Pie family stuff:

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https://www.deviantart.com/lopoddity/art/Sandwiches-Pies-and-Cake-848649552