With layers of fluffy homemade chocolate pudding and crushed Oreos, this is a cup of dirt you'll actually want to eat! My version is 100% from-scratch (no Cool Whip or pudding mix!) and loved by kids of all ages.
In a medium saucepan, whisk together sugar, cornstarch, cocoa powder, and salt.
¾ cup granulated sugar, 3 Tablespoons cornstarch, 2 Tablespoons natural cocoa powder, ¼ teaspoon salt
Add milk and whisk to combine.
3 cups whole milk
Transfer to a stovetop over medium heat and cook, whisking constantly until mixture thickens to a pudding-like consistency and coats the back of a spoon. MIxture will likely bubble as it nears the end of the cooking process.
Remove from heat and immediately add chocolate, butter, and vanilla and whisk until butter and chocolate are melted and all ingredients are smooth and combined.
4 oz dark chocolate bar, 2 Tablespoons unsalted butter, 1 teaspoon vanilla extract
Pour pudding through a fine mesh strainer into a heatproof bowl. Allow to cool for 15 minutes, stirring occasionally. Press a piece of plastic wrap or parchment paper directly against the surface of the pudding (to prevent a skin from forming) and refrigerate until cooled completely, at least 2 hours.
For the whipped cream
Once pudding has chilled, prepare the whipped cream. In a large mixing bowl, use an electric mixer to beat together heavy cream, sugar, and vanilla until thickened and stiff peaks are achieved (mixture will be a Cool Whip consistency).
1 ½ cups heavy cream, ½ cup powdered sugar, 1 teaspoon vanilla extract
Add whipped cream to the (cooled) pudding mixture and use a spatula to gently fold together until combined. Set aside.
Assembly
Crush cookies into fine crumbs (I use a food processor or place them in a ziploc bag and smash them with a rolling pin).
30 Oreo cookies
Scoop about 1 ½ Tablespoons of oreo crumbs into the bottom of your serving cup. Layer with about ⅓ cup pudding, then repeat with another layer of crumbs and pudding and then a final dusting of crumbs on top. If desired, top with gummy worms just before serving.
Gummy worms
Notes
Serving cups
I used 9 oz clear plastic cups for the dirt cups in the photos, however these are fairly large servings! If you want smaller cups, you could alternatively make these in 2-oz disposable plastic shot glasses(affiliate). You’ll get quite a lot more cups!
Oreo Cookies
Alternatively you could make ½ batch of my homemade Oreo cookies and crumble these. I do make and fill the cookies before crumbling them.
Storing
Cover tightly and store in the refrigerator for up to 3 days.