Step 1: Create the Oreo Truffle Filling

1. Crush the Oreos: Place the entire package of Oreo cookies (wafers and filling) into the bowl of a food processor. Pulse until they are broken down into fine, consistent crumbs, resembling dark sand.

   • No Food Processor? No Problem: Place the cookies in a large, heavy-duty zip-top bag. Seal it, removing as much air as possible. Using a rolling pin, meat mallet, or even a heavy can, crush the cookies until they are fine crumbs. This is a great step for kids to help with!

2. Blend with Cream Cheese: Add the softened block of cream cheese to the food processor with the Oreo crumbs. Pulse in short bursts until the mixture is fully combined and comes together to form a large, dough-like ball. If you don’t have a food processor, transfer the crumbs to a large mixing bowl, add the softened cream cheese, and use a spatula or your hands to mix until completely incorporated. The mixture should be thick and easy to handle.

Step 2: Roll and Chill the Pops

1. Portion and Roll: Line a large baking sheet with parchment paper or wax paper. This is crucial to prevent sticking. Using a small cookie scoop (about 1 tablespoon), scoop out portions of the Oreo mixture. Roll each portion between your palms to form a smooth, round ball. You should get approximately 24 balls.
2. The First Chill: Place the rolled Oreo balls on the prepared baking sheet. Transfer the sheet to the freezer and chill for at least 30 minutes. This step is essential! Chilling the balls makes them firm, which prevents them from falling apart when you insert the lollipop sticks and dip them in warm chocolate.

Step 3: Prepare for Dipping

1. Melt the Chocolate: While the balls are chilling, prepare your chocolate. Place the semi-sweet chocolate melting wafers or chocolate chips in a microwave-safe bowl. Microwave in 30-second intervals, stirring well after each interval, until the chocolate is fully melted and smooth. Be careful not to overheat the chocolate, as it can become thick and seize. If your chocolate seems too thick for dipping, stir in 1 teaspoon of coconut oil or vegetable shortening to thin it out.

   • Double Boiler Method: If you prefer, you can melt the chocolate in a double boiler or a heatproof bowl set over a saucepan of simmering water. Stir constantly until smooth.

2. Prepare Decorations: While the chocolate is melting, get your decorations ready. Cut the black licorice laces into 2-inch segments. You will need 8 legs for each spider pop. Have your candy eyeballs open and ready to go. Time is of the essence once the dipping begins!

Step 4: Assemble and Dip the Spider Pops

1. Insert the Sticks: Remove the chilled Oreo balls from the freezer. Dip about ½ inch of the tip of a lollipop stick into the melted chocolate, and then insert that end into the center of an Oreo ball, pushing it about halfway through. The chocolate acts as an edible “glue” to secure the pop to the stick. Repeat for all the balls.
2. The Second Chill (Quick Freeze): Place the pops back in the freezer for another 10-15 minutes. This ensures the sticks are firmly set before dipping, which is the secret to preventing pops from falling off into the chocolate.
3. Dip in Chocolate: Working with one pop at a time, dip it into the melted chocolate, turning the stick to coat the entire ball evenly. Avoid stirring the pop in the chocolate, as this can cause it to loosen from the stick.
4. Remove Excess Chocolate: Gently tap the stick against the side of the bowl, allowing any excess chocolate to drip off. This creates a thin, even coating and prevents a “foot” of chocolate from forming at the base.

Step 5: Decorate Your Spiders

1. Work Quickly: This is the most time-sensitive step! While the chocolate is still wet, it’s time to decorate.
2. Add the Legs: Carefully press four licorice segments into one side of the chocolate-coated pop and four into the other side to create the spider’s eight legs.
3. Add the Eyes: Immediately place two (or more, for a mutant spider!) candy eyeballs onto the front of the pop.
4. Let it Set: Once decorated, you need a place for the pops to set without smudging. You can stand them up in a block of styrofoam, a sturdy glass filled with sugar or rice, or lay them gently back on the parchment-lined baking sheet. If laying them down, know that one side will be slightly flattened.
5. Final Chill: Place the finished spider pops in the refrigerator for 15-20 minutes, or until the chocolate is completely firm and set.