Gooey Almond Chocolate Chess Pie

Kind of like an ultra gooey, super fudgy brownie in an all-butter pie crust, this chocolate lover’s take on a classic chess pie is tough to beat. We’ll use some all star ingredients like almond, brown sugar, coffee, and vanilla to really lift the chocolate up – making it as deep and rich as it can possibly be.

What is Chess Pie?

Chess pie is a custardy, creamy-smooth pie that is made, primarily, from eggs, melted butter, and sugar. Made with a buttery pastry crust, a classic Chess Pie’s simple flavors lend themselves beautifully to any number of flavor riffs. Today, we’re giving a chocolatey spin to the classic recipe, and we’ll call upon some special ingredients to really help us maximize the chocolate flavor in every bite. (More on this in a bit.)

Chess Pie is so cool in that it was a style of pie developed primarily to help put good use to ingredients that had passed their prime. Buttermilk would be used in place of regular milk, vinegar would be used when citrus was not around. Sugar – loads of it – was employed to help kill any bacteria that would try to develop in the other ingredients. 

This is the style of scrappy cooking that I admire and that I wrote a little bit about in my cookbook, Smoke, Roots, Mountain, Harvest. It was made more out of need than want – a type of “waste not, want not” baking that puts to good use certain ingredients to prevent their spoilage, and easily swaps in and out others when they’re scarce. This is less pie for the love of it than pie for practical, resourceful reasons. This is Practicality Pie. But it also happens to be damn delicious, too. Win-win.

I love me a good slice of Practicality Pie. And this gooey chocolate chess pie number? It’s a favorite to be sure. 

Is Chess Pie Southern?

Chess Pie is typically associated with the American South. Many would call it a Southern Pie. But suffice it to say that there is more to this pie’s origin story that meets the pie … I mean eye. Bah!

Ahem. Anyway, there are definitely several fantastic and charming Southern takes on Chess Pie, yes – several iterations of the basic concept. Transparent Pie (native to my home state of Kentucky), Tyler Pie, Vinegar Pie, etc. But pies of this sort were made in New England as well, before and during the time when this method of preservational pie making was being employed in the South.

Why is it called “Chess Pie?”

Honestly though, here is a fascinating piece about one baker’s search for the origins of chess pie’s name. It’s simply not so simple. It appears that the name isn;t easily attached to one person, place, or historical happening. As with so much of our nation’s history, it is not so easy as taking and settling on just one person’s account.

Highly recommend this read. 

Chocolate Chess Pie: Tips and Tricks

1. Blind bake the crust! See below for more about this. It’s a true baker’s need-to-know sort of thing. For me, the single biggest snafu I always make when scratch making pies is not baking my crusts all the way through. I used to always wind up with an amazing filling but that dreaded soggy bottom just PLAGUED me. So, now I faithfully employ a very tried and true blind baking technique (which sounds fancy but is, in fact, not at all) which keeps that from happening.
2. Since this is a chocolate pie, we’ll use a few special ingredients to help lift up the chocolate flavor and really make it shine: coffee, vanilla, and almond. 
3. Speaking of the almond! You can either use almond liqueur or almond extract here. If you opt for the former, use about 1 TBSP in the filling. If you want to use the extract, use much less – about 1 tsp should get you there. 

What cocoa to use in Chocolate Chess pie

Unsweetened. Not all cocoa powders are created equal, turns out. In this recipe, we want the chocolate to add nothing more than its own flavor to the pie – not sweetness. We’re sweetening this pie with brown sugar, so it definitely doesn’t need any more sweetening.

How to Blind Bake

Blind baking is nothing more than pre-baking a raw pie crust, unfilled, to help reduce any chances of side slippage or bubbling up in the center. When you’re working with a homemade crust, the high butter content can cause these two aforementioned issues to occur, but when you take the time to pre-bake – blind bake – you can cut them off at the pass. 

1. Start with a pie crust that has been fitted/shaped inside the pie plate, covered with heavy duty foil, filled with weights (beans, rice, or pie weights), and then frozen for at least 30 minutes. 
2. Bake for 30 minutes at 350 degrees (almost all the way).
3. Remove from the oven, fill with your filling, and then bake until the filling is set/done. 
4. To prevent the edges of your crust from over-browning, you can lay/tent a piece of foil over top as the filling bakes or you can fit the edges with a special crust protector.

Gooey Almond Chocolate Chess Pie: Ingredients

1 pie crust (either homemade, or store-bought)

4 eggs

1.5 cups brown sugar

½ cup unsweetened cocoa powder

1 tsp instant coffee granules

½ tsp kosher salt

10 TBSP unsalted butter, melted

1 TBSP almond liqueur or ¾ tsp almond extract (such as Disaronno, for the liqueur)

2 tsp vanilla extract

½ cup semi-sweet chocolate chips

Powdered sugar or fresh whipped cream, for topping

If you like the looks of this Gooey Almond Chocolate Chess Pie, you might also enjoy:

Lemon Meringue Chess Pie

Alison Roman’s Pie Crust “The Only Pie Crust”

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