Set up three shallow bowls. Place the flour, salt, and black pepper in the first bowl. Pour the buttermilk into the second bowl. Add the panko breadcrumbs to the third bowl.
Heat about two inches of vegetable oil in a large skillet over medium-high heat until it reaches 350 degrees.
Working one slice at a time, dip each pickle into the buttermilk, then the flour mixture, back into the buttermilk, and finally into the panko. Press lightly so the crumbs stick.
Fry the coated pickles in batches for two to three minutes per side until golden and crisp. Remove with a slotted spoon and drain on paper towels.
Let the fried pickles cool for one minute. Add a small dab of cream cheese to the center of each slice, then press an olive round on top to finish the eyeball look.