In a large mixing bowl, cream butter and sugars together for 3-4 minutes. Add in the banana pudding mix and continue to beat for another 1-2 minutes.
Add the eggs and vanilla and beat for 2 more minutes.
Add the flour and baking soda and mix until well combined.
Use a cookie scoop to scoop the cookie dough into a well-greased mini muffin pan. Recipe makes 36 cookie cups.
Bake for 8-9 minutes or until the tops barely begin to turn a light golden brown. Remove from oven and immediately use the back of a 1/2 tablespoon to press an indention into each cookie cup. Don't press all the way to the bottom- you'll want to press the tops about halfway down. Make sure to do this while the cookie cups are hot, straight out of the oven.
Let the cookie cups continue to cool in the pan for about 15-20 minutes and then remove from the pan and cool completely on a wire rack.
When the cookie cups are completely cooled, make the filling. Use a fork or large spoon to mix the pudding mix and pineapple together. Fold in the Cool Whip. Use a small spoon to generously scoop the filling into each of the cookie cups.
In a small glass bowl, mix the chocolate chips and shortening and then microwave for about 30 seconds. Stir and then microwave in 15 second intervals, stirring in between each interval until chocolate is completely melted and smooth. Drizzle on top of the cookie cups and then place a cherry on top of each one. Keep refrigerated until ready to serve.
The cookie cups last pretty well completely assembled in the refrigerator for up to about 24 hours. If you need to make them farther in advance, just make the cookie cups and the filling separately and then wait to add the filling and topping until right before serving.