Chocolate Pudding Pie

Ingredients

• 1¼ cups (156 g) all-purpose flour, plus more for surface
• 6 Tbsp. (¾ stick) cold unsalted butter, cut into ½” cubes
• 2 Tbsp. cold vegetable shortening
• ¼ tsp. kosher salt
• ¼ cup (28 g) cornstarch
• ⅓ cup (67 g) plus 2 Tbsp. sugar, divided
• 3 Tbsp. unsweetened cocoa powder
• ¼ tsp. kosher salt
• 3 cups whole milk
• 4 oz. bittersweet chocolate (not more than 60% cacao), finely chopped
• 1 tsp. pure vanilla extract
• 1 cup chilled heavy cream
• Bittersweet chocolate shavings for garnish (optional)
• Special Equipment: Pie weights or dried beans

Steps

Pastry

1. Work 1¼ cups (156 g) all-purpose flour, 6 Tbsp. (¾ stick) cold unsalted butter cut into ½” cubes, 2 Tbsp. cold vegetable shortening and ¼ tsp. kosher salt together in a medium bowl with your fingertips or a pastry blender, or pulse in a food processor, just until coarse-meal-like with some roughly pea-size butter lumps. Drizzle 2 Tbsp. ice-cold water evenly over it and gently stir with a fork, or pulse, until incorporated.
2. Squeeze a small handful of dough to test whether it holds together. If it does not, stir in more ice water, 1 Tbsp. at a time, until incorporated. Avoid overworking the dough, which will make the pastry tough.
3. Tip the dough onto a lightly floured surface and divide into 4 portions. Smear each portion forward once or twice with the heel of your hand to distribute the fat. Gather it all together, using a pastry scraper if available, and shape a 5-inch disk. Wrap in plastic wrap and chill until firm, at least 1 hour.
4. On a lightly floured surface, use a lightly floured rolling pin to roll an 11-inch round and fit it into a 9” pie plate. Trim to leave a ½” overhang, fold that under and crimp the edge decoratively. Use a fork to prick the shell's bottom and side all over, then chill for 30 minutes.
5. During the shell's chilling time, preheat the oven to 375°F with a baking sheet on the middle rack.
6. Line the shell with aluminum foil or parchment paper and fill with pie weights. Put the pie pan on the hot baking sheet and bake about 25 minutes, until the pastry is set and its edge pale golden. Carefully remove the weights and foil or parchment, then bake on the sheet for 15 to 20 minutes more, until pale golden all over. Let the shell cool.

Pie filling and assembly

1. Whisk together ¼ cup (28 g) cornstarch, ⅓ cup (67 g) sugar, 3 Tbsp. unsweetened cocoa powder and ¼ tsp. kosher salt in a 2-quart heavy saucepan, then gradually whisk in 3 cups whole milk. Bring to a boil over medium heat while whisking constantly; continue boiling and whisking for 2 minutes as it thickens. Off the heat, whisk in 4 oz. finely chopped bittersweet chocolate, not more than 60% cacao, and 1 tsp. pure vanilla extract until smooth.
2. Fill the cooled shell with the warm chocolate pudding. Cover the filling's surface with plastic wrap and refrigerate until cold, at least 2 hours.
3. Immediately before serving, beat 1 cup chilled heavy cream with the remaining 2 Tbsp. sugar just to soft peaks, then spoon it onto the pie. The pastry dough can be chilled up to 2 days. The shell can be baked 1 day ahead: cool it, wrap loosely and store at room temperature. The pie without whipped cream can be chilled up to 1 day ahead.