This was probably one of the more rewarding things I've made because I came up with the idea for it a long time before actually making it, it took a good amount of research and luck to get the crust just right, and it involved doing some things I haven't done before; so when it came out as amazing as it did, I was stupidly happy. A lot of recipes for chocolate chip cookie crust say to either buy or make regular cookie dough, and that doesn't really work because once the dough starts cooking, it gets a bit more viscous before it solidifies and the sides melt down into the bottom of the pan, so while you end up with a really good giant cookie, a pie crust it ain't. I ended up combining the best cookie dough recipe I've found so far (This one) with the only one I found that had a solution for the "giant cookie 'problem'" (This one). Funny thing though, I didn't notice until way too late that that second recipe was for a more decadent version of what I was making. I was looking at it purely for the crust and ignored the filling entirely. By the time I actually looked at it fully and realized that when they said "custard" they meant "pudding", I already had pudding packs and was ready to go. Besides, custard is hard as fuck to make well and pudding packs come out just as good. Compare that one to this one and decide for yourself which one you'd rather make, combine elements like I did, whatever. Just shovel this dish into your piehole ASAP and I guarantee it'll make your fuckin day.
4 tablespoons room temperature butter
2 tablespoons room temperature cream cheese
1/3 cup of sugar (roughly 2/3 of which should be light brown sugar, the other 1/3 regular white sugar)
1 cup all purpose flour
1-2 teaspoons vanilla extract (I ran out somewhere around the 1 1/2 mark because I'm a dumbass who doesn't bother to check if I have enough of something, I stop at "do I have it at all?" and start cooking. Do as I say, not as I do)
3/4 cup of semi-sweet chocolate chips
2 packs of Jello chocolate pudding
3 1/2 cups of milk
1 small carton of heavy whipping cream
1-2 teaspoons or so of sugar (I eyeballed it because I made this part at somebody else's house and didn't feel like hunting around for measuring spoons)
Pre-heat oven to 350 degrees Fahrenheit. In a medium-size bowl, beat the sugar, butter and cream cheese together with a fork or wire whisk (I find whenever I use a wire whisk on semi-solid ingredients I end up with a ball inside the whisk that's a bitch to get out, so I use a fork). Add the flour, salt and vanilla extract and mix until it looks like sand but you can pinch some of it between your fingers and it'll stay together for at least a few seconds. Mix in the chocolate chips. Press the sand-dough into a non-stick-spray-lined pie pan, making sure that the corner between the bottom and the sides doesn't get too thick. The whole crust should be about one chocolate chip deep. Bake the crust for 20-25 minutes until the sides start to turn slightly golden brown and the bottom looks about the same as it did before you put it in the oven but will hold up to a light poking without falling apart. Start checking on it every few minutes around the 15-minute mark. Chill the crust.
Combine the pudding mix and milk and heat in a large pan over medium heat (err on the low side and turn it up if need be or you'll burn the shit out of the bottom of the pudding and be cleaning the pan for days. Trust me) until it starts boiling. Take the pot off the burner and let it cool for about half an hour before pouring the pudding into the pie crust, insert 4 toothpicks in a square formation into the pudding but don't pierce the crust, cover with plastic wrap so that the toothpicks prevent the plastic wrap from touching the pudding, and refrigerate until the pudding fully sets (at least 1-2 hours, depending on how cold you keep your fridge). If the toothpicks fall and the plastic wrap touches the pudding, it's not a big deal but some pudding will come away with the plastic wrap when you uncover it.
Chill a metal bowl and, depending on what you have for kitchen equipment, a wire whisk/wire whisk attachment for a stand mixer/the mixing blades of a handheld mixer in the freezer for about 15 minutes. Pour the whipping cream and sugar into the bowl and beat for about 5-10 minutes until stiff peaks form. If you're using a wire whisk (which, lemme tell ya right now, unless you jerk off like 6 times a day, if you go that way your arm's gonna fall the fuck off) or handheld mixer, make sure to turn the bowl and move your mixing area around as much as possible to beat the cream evenly. Once the cream looks like it's getting close to the right consistency, start trying to form the peaks with whatever mixer you're using because they won't form just by beating the cream with the wire/blade constantly going all the way to the bottom of the bowl.
Using a large knife, cut the pie into 8 equal slices. Make sure to make each cut very small and don't try to move the knife all the way across the pie or the crust will crumble. It's more of an up-and-down cut than a sawing or one-cut slicing motion at first and then you can move the blade gently across to make sure you didn't miss any spots. Serve each slice in a bowl or on a plate with a large spoonful or two of whipped cream on top and enjoy.