Gather all ingredients.
Heat 2 inches oil in a large, heavy-bottomed pot over medium heat to 350 degrees F (175 degrees C). Line a plate with paper towels and set aside.
Meanwhile, hollow out inside of pickles using an apple corer leaving a ⅛-inch border; discard seeds and pulp.
Combine pork and Cheddar in a medium bowl; stuff into each pickle (3 to 4 tablespoons per pickle).
Place ½ cup flour in a shallow dish. Pat stuffed pickles dry with paper towels; roll in flour until lightly and evenly completely coated.
Insert a (6-inch) skewer lengthwise through each pickle.
Whisk remaining ½ cup flour, cornmeal, cornstarch, sugar, baking powder, salt, and black pepper together in a medium bowl; whisk in buttermilk and egg until smooth.
Pour batter into a tall glass. Dip 1 pickle into batter, letting excess drip off; immediately and carefully lower battered pickle into hot oil.
Fry, flipping often, until golden all over, 4 to 5 minutes. Transfer to the prepared plate to drain. Repeat battering and frying with remaining pickles.
Drizzle pickles with ranch dressing and BBQ sauce. Serve with more sauce on the side. Recipe developed by Nicole Hopper
