Deep, dark chocolatey cookies topped with a creamy vanilla frosting and decorated to resemble the legendary Pumpkin King, Jack Skellington!
Growing up, I was OBSESSED with the The Nightmare Before Christmas. Not only did I find the storyline intriguing, but the stop-motion animation was incredibly captivating and the music was extraordinary. I loved that it revolved around my two favorite holidays–Halloween and Christmas. I don’t care what anyone says, it has to be the best holiday movie ever made!
So with Halloween JUST around the corner, I decided to make a treat to honor both the spookiest holiday of the year as well as one of the most iconic films ever made…
How flippin’ cute are these cookies??
Without a doubt, these little guys would be the perfect treat to serve at your next Halloween party! And if you have any kiddos, I’m absolutely certain they’d LOVE decorating these cookies. Heck, I even had a blast putting the little Jack Skellington faces on each one!
Not only do these cookies look super cool, but they taste absolutely incredible!! That’s because these cookies aren’t just your average chocolate cookie. They’re packed with a richer, dark chocolatey flavor that’s reminiscent of an Oreo. But instead of having the crispy texture of an Oreo, these cookies are soft, wonderfully thick, perfectly moist and slightly chewy. Not the least bit cakey or crumbly.
In order to achieve that rich Oreolicious flavor, these cookies get a hefty amount of cocoa powder–3/4 of a cup, to be exact. I used Hershey’s Special Dark cocoa powder which is basically Hershey’s version of dutch-processed cocoa. It’s darker and richer than natural cocoa powder, and it lends a more decadent dark chocolate flavor to baked goods.
The cocoa powder is combined with flour, baking soda, baking powder, salt, and cream of tartar. The cream of tartar gives these cookies a lighter, slightly chewy texture with a tender crumb.
Another key ingredient in creating that perfect balance of softness and chewiness is cream cheese. It also adds depth, density, and richness to the cookie. After the cream cheese and butter are combined, the rest of the wet ingredients are added–oil, granulated sugar, powdered sugar, brown sugar, egg, vanilla, and espresso powder. The espresso powder helps to enhance the flavor of the cocoa. Just a little is needed to achieve that intense richness without adding any coffee flavor.
Since Jack Skellington’s classic colors are black and white, I decided to add some black food coloring to the dough to make it EXTRA dark. However, if you don’t have any food coloring or you like the dough the way it is, don’t worry about adding it.
To frost these cookies, I just went with a simple vanilla American buttercream frosting. I don’t know what it is, but there’s something so divine about a rich dark chocolate cookie with white vanilla frosting. It probably has to do with the deep contrast between the two flavors.
When tinting the frosting black for the facial features, I recommend stirring in a tablespoon or two of cocoa powder first. This will help darken the white frosting, so that you don’t have to add as much black food coloring. I ended up making a small batch of new frosting because I added too much food coloring, which caused it to break/separate.
To get all of the face designs, I just Google image searched “Jack Skellington face” and a bunch of different facial expressions popped up. You can either print them out, or have them open on your phone like I did. I would suggest using a skewer or toothpick to create a “first draft” on your cookie. That way you can trace those lines with the black icing.
Fun, festive, and ghoulishly good, these Jack Skellington Cookies are guaranteed to be a hit at your next spooky celebration!
Jack Skellington Cookies
Ingredients
Chocolate Cookies:
- 2 cups all-purpose flour
- ¾ cup cocoa powder
- ½ teaspoon cream of tartar
- ¼ teaspoon baking soda
- ¼ teaspoon baking powder
- ½ teaspoon salt
- ½ cup unsalted butter softened
- 2 ounces cream cheese
- ⅓ cup vegetable oil
- ½ cup granulated sugar + 3 Tablespoons divided
- ½ cup powdered sugar
- ¼ cup brown sugar
- 1 egg
- 1 teaspoon vanilla
- ¼ teaspoon instant espresso powder
- 1 Tablespoon black food coloring (optional)
Vanilla Frosting:
- 1 cup unsalted butter at room temperature
- Pinch of salt
- 1 teaspoon vanilla
- 4 cups powdered sugar
- 3-4 Tablespoons milk
- 1 Tablespoon cocoa powder (optional)*
- Black food coloring
Instructions
Make the Cookies:
- 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.
Make the Frosting:
- 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.