Place bacon chunks and bourbon in an airtight container, like a mason jar, and let sit for 3 hours on the counter. Remove bacon, recover container, and place in the fridge for 2 hours to solidify the fat from the bacon.
Strain bourbon through a fine mesh sieve. Set aside.
Place the 12 plastic cups in a baking pan.
Pour the gelatin into a medium mixing bowl. Add cold water and stir to combine. Let sit until all the gelatin has been absorbed.
Add boiling water, and whisk until gelatin has dissolved. Add brown sugar and whisk until dissolved.
Pour in apple juice and bacon-infused bourbon, stir to combine.
Pour the apple juice mixture into the plastic cups, distributing it evenly, and filling until just about to the top.
Place the baking dish in the refrigerator for 6 hours, or until the jello has set.
Preheat oven to 400 degrees F. Line a baking sheet with foil and coat with non-stick cooking spray.
In a small bowl combine the brown sugar and cayenne. Pour onto a plate and spread into an even layer.
Lay the bacon strips on top of the brown sugar, and press down to coat the bacon. Flip the strips over and repeat. You want a good coating of sugar. Lay the bacon on the prepared baking sheet.
Bake for 7 minutes, carefully flip the bacon over and bake for another 5 minutes. (Watch the bacon so it doesn't burn!) Remove from the oven. Transfer the bacon to a plate coated with non-stick cooking spray and let rest until cool. Chop the bacon into tiny pieces (think bacon sprinkles).
Pour about 1/2 teaspoon crumbled bacon on to each jello shot and spread into an even layer. Place a plastic lid on each cup and store in the fridge until ready to serve.
Two different types of bacon are used for this recipe. Regular cooked bacon to infuse the whiskey, and then a separate batch of canided bacon to go on top of the shots.