In a stand mixer fitted with a paddle attachment, cream butter and sugar together.
Add eggs and vanilla.
Add flour, baking powder and salt. Mix until just combined.
Cover with plastic wrap and chill in the fridge for at least one hour.
When the dough is chilled, preheat the oven to 400 degrees F and prepare a baking sheet with parchment paper.
On a floured surface, roll out the dough to 1/4" thick.
Use the cookie cutter to cut out circles and place them on the baking sheet.
Bake for 6 - 8 minutes. Place on a wire rack to cool.
Once the cookies are cooled, melt 14 oz of melting chocolate according to the instructions on the package.
Dip half of the cookie into the chocolate and place on parchment paper.
Use a toothpick to make a small tie on one side of the hat and add sprinkles.
Once the hats is dry, melt the 4oz of chocolate.
Dip the toothpick into the melted chocolate and draw on the pirates face.