Step 1: Prepare the Oreos

1. Line Your Baking Sheets: Before you begin, line two large baking sheets with parchment or wax paper. This will be your workspace and a place to lay down pops if needed.

2. Insert the Lollipop Sticks: This is a delicate but crucial step. Take a Double Stuf Oreo and a lollipop stick. Gently open the Oreo by twisting it slightly. You don’t need to separate it completely. Lay the stick in the center of the creme filling. Gently press the cookie back together, sandwiching the stick firmly in the creme.

3. Alternative Insertion Method: A more secure method is to dip the tip of the lollipop stick into a little bit of the melted candy melts (from a later step) before inserting it into the creme filling. This acts as an edible glue, ensuring the cookie won’t slide off the stick.

4. Repeat: Continue this process for all 18-20 Oreos, laying them flat on the prepared baking sheet as you go.

5. Chill the Oreos: Place the entire baking sheet of prepared Oreo pops into the freezer for at least 15-20 minutes. This step is vital! Chilling the cookies makes them very firm, which prevents them from breaking or falling off the stick when you dip them into the warm, melted candy coating. Do not skip this step.

Step 2: Melt the White Candy Coating

1. Microwave Method: Pour the bright white candy melts into a microwave-safe bowl. Microwave on 50% power for 1-minute intervals. Stir well after each interval. Continue this process until the melts are almost completely melted but a few lumps remain. Remove from the microwave and stir continuously until the residual heat melts the remaining lumps, resulting in a smooth, fluid consistency. Be very careful not to overheat the candy, as it can burn or “seize,” becoming thick and unusable.

2. Double Boiler Method: If you prefer, use a double boiler. Fill the bottom pot with an inch or two of water and bring it to a simmer. Place the candy melts in the top pot (or a heat-safe bowl that fits snugly over the bottom pot without touching the water). Stir frequently until the candy is completely melted and smooth.

3. Thin the Coating: Once melted, check the consistency. If it seems too thick for dipping, stir in 1 teaspoon of Paramount crystals, coconut oil, or shortening. Continue to add in small increments until you reach a smooth, fluid consistency that drips easily from a spoon.

4. Transfer for Dipping: Pour the thinned, melted candy into a tall, narrow glass or mug. This allows you to submerge the entire Oreo pop in one go, creating a much cleaner and more even coat.

Step 3: Dip and Dry the Pops

1. Remove Oreos from Freezer: Take only a few Oreo pops out of the freezer at a time, leaving the rest to stay cold until you are ready for them.

2. Dip the Pop: Hold a pop by the stick and fully submerge the Oreo into the melted candy in the tall glass. Ensure the entire cookie is coated.

3. Remove Excess Coating: Lift the pop straight out of the candy. Gently tap the stick on the rim of the glass, rotating the pop slowly. This is the most important part of getting a smooth finish. Tapping allows the excess coating to drip off evenly, preventing a thick, lumpy coat and “feet” from forming at the base. You can also use a spoon to gently scrape any excess off the back of the pop.

4. Set to Dry: Once the excess has been tapped off, immediately place the pop upright in your styrofoam block or prepared box to dry. The candy coating should start to set fairly quickly. Do not lay them flat, as this will ruin the round shape.

5. Repeat: Continue this dipping and drying process with the remaining Oreo pops until all are coated. Let them dry completely at room temperature for at least 30-45 minutes, or until the surface is hard and no longer tacky to the touch.

Step 4: Decorate Your Jack Skellingtons

1. Ensure Pops are Dry: Before you begin decorating, gently touch a pop to make sure the white candy coating is completely hardened. If it’s still soft, your edible marker will smudge and ruin the surface.

2. Draw the Face: Using your fine-tipped black edible food writer, it’s time to bring Jack to life!

   • Eyes: Draw two large, elongated oval or teardrop shapes for the eyes. Fill them in completely with the black marker.

   • Nose: Add two small, thin vertical slits for his nostrils, placed between and slightly below the eyes.

   • Mouth: Draw a long, thin, slightly curved line for the mouth, extending almost to the edges of the Oreo. Finish the look by drawing small vertical “stitch” marks all the way across the mouth line.

3. Be Creative: Don’t worry about making every single face identical. Part of the charm of “The Nightmare Before Christmas” is its quirky, imperfect aesthetic. Some Jacks can be smiling, others can have a more surprised expression.

4. Let the Marker Dry: Allow a few minutes for the edible ink to dry completely before you handle or package the pops.