I’m not even going to get into “Why is it called chess pies?” Some things must be accepted as-is, which, for better or worse, strikes me as a particularly Southern attitude. (Personally I subscribe to the corruption of “cheese pie.”)
In my mind, this is one of the quintessential Southern pies. It’s up there with sweet potato and pecan pie. This is the definition of a desperation or a pantry pie (first google hit for "pantry pie")—eggs, sugar, butter, milk—everything a farm kitchen would have. Vanilla is the only fancy part. Like a lot of Southern food, it’s deceptively simple. You mix it like a cookie—cream the butter and dries, incorporate the eggs, then the milk and vanilla. These basic ingredients combine for a salted, caramel-butterscotch filling greater than the parts.
The recipe is nothing special to read. It’s a like any other in a thousand cookbooks, but it’s my Grandma Shorty's. My grandmother, her step-daughter, would bring them back from visits to Cooleemee, North Carolina, and I’d try not to make myself sick on them.
Now, looking at Grandma Shorty’s recipe, there’s no salt. I’m guessing she used salted butter. I’ve taken the liberty to add a pinch. She also used a Crisco crust, but I’ve opted for the butter and lard I typically use. She would pour the filling into unbaked shells and bake them whole, I’m par-baking the shells to avoid unbaked bottoms and for extra crispness. But I’m baking them like Shorty did, in individual pot pie tins. Individual tins will have a higher crust to filling ratio, which, considering how sweet and rich the filling it, is a good balance.
Like the buttermilk pie, the basic chess can be a base for multiple variations. A splash of apple cider vinegar to cut the fat, some spirits for the adult palate. Toss chocolate chips on the bottom, fold-in some cocoa powder. Swap out the brown sugar for white and add citrus zest and Cointreau. Half-and-half instead of milk for a richer filling. Coconut. Buttermilk. On and on.
- Enough pastry dough to line 18 or so individual pie molds.
- 2c Brown Sugar
- 2 Eggs (3.5oz)
- ½c Butter, softened
- ½c Milk (skim, pet, or whole)
- 2Tbls Flour
- 1tsp Vanilla
- ¼tsp Salt
- Line, parbake, and cool the miniature pie shells. Cupcake liners weighted with sugar works well.
- Turn oven down to 325˚.
- Lightly cream butter, sugar, salt, and flour.
- Slowly incorporate eggs.
- Whisk in milk and vanilla.
- Fill baked shells.
- Bake at 325˚ till center is almost set. 20-30 minutes.
- Cool and eat!