Cut each pickle in half across the equator. Use an apple corer, melon baller or the tip of a small knife to hollow out the interior of each pickle half, leaving an 1/8-inch-thick border of pickle intact. Slice the closed end of each pickle shot glass just enough to make it sit flat. Be sure not to cut too deep and create a hole in the shot glass.
Fill each pickle shot glass with 1 tablespoon of bourbon. Serve immediately.