Chocolate Chip Pie (Chess Pie) Recipe

Have you ever had a southern Chess Pie? I hadn’t until recently and now I am OBSESSED. This Chocolate Chip Pie is my new favorite.

Chocolate Chip Cookie in whipped cream in chess pie

Why You’ll Love This Chocolate Chip Pie

A delicious dessert made with pantry ingredients that everyone will love? Yes, please!

A fun twist on a classic – While a traditional chess pie is just the custard filling, this one takes it up a notch by adding chocolate chip cookies!
Perfect for any occasion – Whether you serve it with a scoop of ice cream or just on it’s own, this pie is great for serving at picnics, after dinner and just about anywhere else you can think of.
Pantry ingredients – I’d be willing to be you have almost all of these ingredients, if not most, already in your kitchen.

What is Chess Pie?

Chess Pie is traditionally southern pie using a sweet custard filling. The roots actually come from England and date back to early settlers.

How is got its name vary from story to story, but these are the two accepted versions. First being that men were served this sweet pie while rotating from room to room while playing in chess tournaments. The second is that southern drawl changed “jus’ pie” to “chess pie”.

The most common chess pie recipes are traditional (like the base for this recipe), chocolate chess pie, lemon chess pie and buttermilk chess pie.

Chess Pie is a slightly sweet pie that is basically baked sugar. The oddball ingredient, white vinegar, is what cuts the sweetness. I got the idea to incorporate cookies into my Chess Pie after having a slice of Dangerously Delicious’ Baltimore Bomb Pie.

Overhead shot of slice of Chocolate Chip Pie on a white plate with cookie crumbles

What You’ll Need

You will easily be able to find these chocolate chip pie ingredients at any local grocery store.

Deep dish frozen pie crust – If you have a favorite flaky pie crust recipe, feel free to use it! I despise making pie crust, so I prefer to use pre-made.
Butter – I always prefer to use unsalted butter so that I can control the salt content, but you can use salted butter in a pinch.
White sugar – To add an element of sweet to this pie, we just need plain granulated white sugar.
Eggs – Always assume a recipe is calling for large eggs. It’s also best if they are used at room temperature.
Yellow cornmeal – Cornmeal helps in thickening the batter and adds what some call a chewy element that all purpose flour wouldn’t provide.
White vinegar – You need something acidic to cut through the extreme sweetness from baked sugar. Some recipes use vinegar, others use buttermilk or lemon juice.
Vanilla extract – Vanilla adds a warmth and flavor to this pie that is unmatched. Make sure to use a good quality vanilla.
Heavy cream – This helps to thin out the batter a bit, while also giving it that creamy texture.
Chocolate chip cookies – We add these to the pie batter, but also use them as a garnish on top.
Whipped cream – This is optional, but I love topping my pie with dollops of whipped cream.

Variations

There are plenty of ways you can make this chocolate chip pie recipe your own. Here are a few ideas.

Nuts – If you’d like to add a little more crunch to your pie, stir in some chopped nuts like walnuts or pecans.
Chocolate chips – To add even more chocolatey goodness to this toll house pie, spoon in some semi-sweet chocolate morsels. My favorite are nestle. Of course you can use any blend of chips including dark chocolate, white chocolate, peanut butter, toffee or anything else you can dream up.
Cookies – Instead of chocolate chip cookies, satisfy your sweet tooth in a different way with your favorite cookie recipe.

Chocolate Chip Cookie in whipped cream in a chocolate chip pie

Who doesn’t like chocolate chip cookies? Only the same people who don’t care for puppies or rainbow colored unicorns, that is who. (No offense if you don’t like puppies or unicorns.) Peanut butter cookies work too.

As for the cookies, make them from scratch or buy them at the store. Make sure they are large chocolate chip cookies, not the little Chips Ahoy ones though. I prefer getting chewy or soft cookies because as they bake, they harden a little. The pie itself is soft and a crispy cookie will just get crisper.

How to Make Chocolate Chip Pie

Making this homemade pie couldn’t be easier.

Beat butter and sugar. In the bowl of stand mixer or a large bowl with a whisk or hand mixer, beat butter until light and fluffy. Add sugar, creaming well.
Add eggs. Then add eggs, one at a time, mixing well each time.
Add remining ingredients. Add yellow corn meal, white vinegar, vanilla and heavy cream. Batter will be rather soupy, this is correct.
Add cooking and pour batter. Break cookies into pieces in the unbaked pie shell. Pour chess pie batter over cookies.
Bake. Place on a rimmed baking sheet. Bake, reduce temperature and bake again. Pie will be soft in center, but not jiggly.
Cool, cover and chill. Allow to cool on a wire rack. Cover and refrigerate.
Garnish and serve. Keep chilled until ready to serve. Serve at room temperature with chipped cream and additional crumbled cookies.

Tips and Tricks for Perfect Chess Pie Recipe

This pie recipe can be a little finicky, so follow these steps to make sure it turns out perfectly every time.

Place pie on a baking sheet. It doesn’t effect the actual pie, but makes it easier to get it in and out of the oven.

Make sure your butter is room temperature. The pie batter is rather soupy and if your butter isn’t perfectly creamy, it causes lumps.

Sift your flour. Again, because the batter is creamy, it is more prone to lumps.

Make sure you use a DEEP dish pie crust. A regular one won’t hold all your goodies and it will just come oozing out the side. Then you’ll have burnt sugar in the oven. Yuck!

Storage and Freezing

You can make a Chess Pie ahead, but I would suggest doing it no more than 24 hours before you plan to serve.

How to Store Chocolate Chip Pie

After it is cooked, there is no need to refrigerate your pie unless you are just trying to preserve it. It can stay at room temperature indefinitely and was typically served at room temperature.

Like most baked goods, it is best right after being prepared, but can will stay good up to 5 days.

Can I Freeze Chess Pie?

I have not tried to freeze this pie, but I don’t see why not as long as you package it well. It should last up to 4 months. Defrost fully before serving, but don’t use the microwave to do so. Allow it to cool completely before prepping and freezing. Thaw in the fridge overnight or at room temperature.

Side angle showing inside of chess pie slice

Questions About Chocolate Chip Pie

What do you add cornmeal to Chess Pie?

Is “because that is how you do it” an answer? It helps in thickening the batter and adds what some call a chewy element. Listen, I am not claiming to be a Chess Pie expert, I’m just trying to do my research and learn as much as I can.

Why do you add vinegar to chess pie?

You need something acidic to cut through the extreme sweetness from baked sugar. Some recipes use vinegar, others use buttermilk.

How do you keep Chess Pie from cracking?

Like cheesecake, you can use a water bath to prevent your pie from cracking. But honestly, since this one uses chocolate chip cookies and gets another garnish of cookies, it really isn’t necessary.

The garnish will cover any imperfections and just because your pie cracked doesn’t mean it doesn’t still taste great!

How do I know my chess pie is done?

The most common mistake in making a chess pie is overcooking it. The pie is done when the center is still slightly jiggly.

You might be tempted to let it go a few minutes longer, but I beg you to take it out NOW. It will set just fine. I promise. If sticking a knife in, it will not come out clean.

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