Preheat the oven to 350ºF. Line a baking sheet with parchment paper, or spray with nonstick cooking spray.

In a large bowl, whisk the flour, cocoa powder, cream of tartar, baking soda, baking powder and salt together; set aside.

In the bowl of a stand mixer fitted with a paddle attachment, mix the butter and cream cheese together until smooth and creamy.

Add the vegetable oil, 1/2 cup granulated sugar, powdered sugar, brown sugar, egg, vanilla, espresso powder, and food coloring and mix until fully incorporated. Gradually stir dry ingredients into wet ingredients until dough comes together. Cover and chill dough in the refrigerator for 1 hour.

Place remaining 3 Tablespoons of sugar into a small bowl. Form dough into balls about the size of a golfball, roll in sugar, then place on lined baking sheet. Repeat process with more dough until you have 8 or so balls spaced 2 inches apart. Using the bottom of a glass, flatten each dough ball to about 1/2" thickness. It's okay if the cookies form a rim on the edges.

Bake cookies for 7-8 minutes or until tops look mostly dry around the edges, yet still glossy in the center--no browning. Remove from the oven and allow to cool on the baking sheet for 3-4 minutes before transferring to a wire rack to cool completely.

In the bowl of a stand mixer fitted with the paddle attachment, beat the butter, salt, and vanilla on high speed until lightened and creamy. Add the powdered sugar, a cup at a time, until just combined. Scrape down the sides of the bowl, add the milk, and beat on high until fluffy, about 2-3 minutes.

Using an offset spatula spread the frosting evenly over the entire surface of each cookie.

Using a skewer or toothpick, draw a "first draft" of the Jack Skellington faces on each cookie.

Add the cocoa powder and black food coloring to the remaining frosting. Transfer black frosting to a piping bag fitted with a small round tip. Using the skewer tracings as a guide, pipe the black frosting onto the cookie.