A delicious showstopper of a cookie. I make these cookies for Christmas, and more recently had a request for them for a wine tasting party. My father has proclaimed them "the most delicious cookie I have ever tasted". Mission Accomplished.
Notes from the Test Kitchen:
These are dynamite! Think ice cream sundae in cookie form! With their brownie-like cookie base and creamy cherry topper, we wiped out the first batch in record time. No shame in that, folks. You'll see what we mean when you give these a try for yourself!
Prepare cookie base. Melt unsweetened chocolate with a double boiler (or the microwave in 30 second increments.)
In a separate bowl, add chocolate to the oil, sugar and vanilla. Mix until well incorporated.
Stir in eggs, flour, baking powder and salt; Mix well. Chill for 2-3 hours.
Remove from refrigerator. Roll dough into one inch balls. bake at 350° for 10 minutes, this will give you a softer cookie. (Up to 12 minutes if you desire a crispy cookie. I prefer soft. )
Once you have removed the cookies from the oven, immediately use a round bottomed spoon (a teaspoon measuring spoon is a good size) to smoosh a "well" into the cookies. Allow to cool completely.
Prepare cookie filling. In a medium bowl, mix softened butter (not melted), confectioners sugar and rum extract (or rum) for flavor. You may need a little more than a teaspoon, depending on your taste. Blend using a hand mixer until it is the consistency of piping frosting. Add 1/4 cup of milk chocolate chips, finely chopped.
Using a pasrty bag without a tip, pipe a dollop of filling into the well you pressed into the cookie. Add a Maraschino cherry to the top of each cookie. The ones with stems are very pretty.
Melt the remaining milk chocolate chips and drizzle over the cookies. NOTE: The cookies in the main picture are a "bite sized version" of this cookie - When I rolled the ball they were about the size of the cherries before baking.