Chocolate Cookies & Cream Pudding

Since yesterday I was chatting with you about staples (staple ingredients, not the office supply store), I figured I would stick with that theme: a staple of my childhood was pudding.

When I set out to make my first ever batch of homemade pudding, all these memories from my childhood came to mind.

In our house, we coveted snack packs like nobody’s business. Even Billy Madison would not be able to compete with the lengths we went to, hoping to keep our personal pudding stashes safe.

My youngest brother, Zack, always ate all of the chocolate pudding cups. I am not kidding. He could sit down and demolish a four pack of pudding cups. Isn’t that such a youngest sibling thing to do??  Anyway, once they came in the house, me and my other brother Nick would have find a hiding spot or eat them before Zack got to them.

If there was ever any food I wanted to keep safe, I ventured to the basement. It was dark and scary and none of us kids really ever wanted to go down there alone. We kind of had that Kevin McCallister fear of the furnace in the basement.

I would put my food stash in the crisper in the basement refrigerator. I also used to hide chocolate, Pepsi, Coke, and Cadbury Eggs in that blessed crisper. My stashes were safe for a year or two before one of my brothers courageously ventured into the cellar (that sounds way creepier than basement), found it, and raided it.

My next pudding move was to start freezing them. I know, kinda weird, but it was safe because nobody wanted a frozen pudding cup. My logic was it was just like a pudding pop or a Wendy’s Frosty. The only issue was that I had to use a grapefruit spoon to cut through the frozenness.

Now that I am out on my own and don’t have to hoard my favorite food away from my brothers, I can enjoy my pudding cups in peace without having to share with anybody! But, being the nice sister that I am, I put most of this batch of chocolate cookies and cream pudding in Tupperware to give to my baby brothers. (Don’t think I’m that nice. This is also self-serving. I don’t need to eat five servings of this! They can handle it with their youthful metabolisms.)

Ingredients (Makes 5 Pudding Cups)

For the Chocolate Pudding:

2 Tablespoons Granulated Sugar

2 Tablespoons Cornstarch

2 Tablespoons Unsweetened Cocoa Powder

2 Teaspoons Instant Coffee Powder

Pinch of Salt

1 ½ Cup Whole Milk

¾ Cup Heavy Cream

4 Ounces Milk Chocolate, coarsely chopped

1 Teaspoon Pure Vanilla Extract

For the Whipped Cookies and Cream:

2 Cups Heavy Cream

¼ Cup Powdered Sugar

1 Teaspoon Pure Vanilla Extract

12 Chocolate Sandwich Cookies, crumbled

Whisk together the sugar, cornstarch, cocoa powder, instant coffee, and salt in a medium saucepan. Set over medium/high heat. Slowly pour in the whole milk and heavy cream while whisking. Continue whisking while the pudding comes to a slight simmer. Keep that whisk going while you let the pudding come to a boil for two minutes. The pudding should be starting to look more like a pudding at this point.

After two minutes, remove from heat. Add the chocolate and vanilla extract. Whisk until all the chocolate has melted into the pudding.

Pour the pudding into a medium bowl. Cover with plastic wrap, making sure that the top of the hot pudding is touching the plastic wrap. This will eliminate a “pudding skin” from forming (NOTE: please feel free to omit this step if you are a George Costanza-type).

Refrigerate the pudding for at least two hours.

Meanwhile, get started on the cookies and cream whipped topping. Add the heavy cream to the bowl of a stand mixer fitted with the whisk attachment. Start to beat the cream on medium high speed until soft peaks start to form. Stop the mixer and then add in the powdered sugar and vanilla extract. Beat the cream and sugar until stiff peaks start to form.

Place 12 chocolate sandwich cookies in a small plastic storage bag. Smash them with a mallet or use your fingers to crumble them into small pieces. Fold the cookies into the whipped cream.

Switch off layering chocolate pudding and cookies and cream in a clear glass serving vessel. Top off with some more cookie crumbles. Pudding and whipped cookies and cream last four days in separate air tight containers stored in the refrigerator.

recipe from Joy the Baker