Equipment Needed
- 9×13 inch baking pan
- Electric hand mixer or stand mixer
- Large mixing bowls
- Whisk
- Small saucepan or kettle
- Fork or the end of a wooden spoon
- Measuring cups and spoons
- Spatula
- Food processor or zip-top bag and rolling pin for crushing cookies
Step-by-Step Instructions
First, I bake the chocolate cake according to the package directions in my well-greased 9×13 pan. I let it cool just until it’s warm to the touch—this is crucial. If it’s too hot, the pudding will melt into a puddle; too cold, and the holes won’t form as easily. Using the handle of a wooden spoon, I poke holes all over the cake, about an inch apart. I go almost, but not quite, to the bottom. The first time I made this, I was too timid with my poking and the pudding just sat on top. Be generous with those holes! They’re the secret tunnels for all that creamy goodness.
While the cake is cooling, I make the pudding filling. In a large bowl, I whisk the two boxes of instant vanilla pudding mix with the four cups of cold milk for a full two minutes. I set a timer because under-whisking leads to a runny pudding. After letting it set for about 5 minutes, I fold in the thawed Cool Whip and about three-quarters of my crushed Oreos (I save some for the top!). The mixture will be thick and speckled with cookie bits—it’s absolutely heavenly.
Now for the fun part: assembly. I carefully pour and spread my thick pudding mixture over the warm, poked cake. I use my spatula to gently push the filling down into all those little holes, watching it disappear into the cake’s core. This is where the magic happens. I then smooth the top, cover it lightly with plastic wrap, and pop it in the refrigerator. You must let it chill for at least 4 hours, but overnight is truly best. The wait is agonizing, but it allows the cake to absorb the pudding and become unbelievably moist and cohesive.
Finally, the grand finale. Right before serving, I spread the remaining Cool Whip (or a fresh batch of whipped cream) over the top of the set cake. I sprinkle it generously with the reserved crushed Oreos. Slicing into that chilled, layered masterpiece and seeing the beautiful pudding-filled channels is so satisfying. Every single bite is a perfect mix of soft cake, creamy filling, and that iconic cookies-and-cream crunch.(See the next page below to continue…)