Instructions

for the crust

Adjust oven rack to middle position and heat oven to 325 degrees. Process 6 ounces crushed shortbread cookies, ⅓ cup toasted pecans, 2 tablespoons flour, and ¼ teaspoon salt in food processor until finely ground, about 30 seconds. Add 3 tablespoons granulated sugar and 4 tablespoons melted unsalted butter and pulse until combined, about 8 pulses, scraping down sides of bowl as needed. Transfer mixture to 9-inch pie plate.
Using your hands, press crumbs firmly up sides of plate, building walls and leveling top edge. Press remaining crumbs into even layer on bottom of plate, firmly pressing crumbs into corners of plate. Bake until fragrant and beginning to darken at edges, 18 to 20 minutes. Transfer plate to wire rack and allow to cool, at least 15 minutes.

for the cream cheese layer

When crust is cool, process 8 ounces softened cream cheese, ⅓ cup confectioners’ sugar, 3 tablespoons heavy cream, and 1 teaspoon vanilla in clean food processor until smooth, about 15 seconds, scraping down sides of bowl as needed. Transfer to cooled pie crust and spread into even layer. Refrigerate while making pudding.

for the chocolate pudding layer

Combine ¼ cup (1¾ ounces) granulated sugar, ¼ cup (¾ ounces) Dutch-processed cocoa powder, ¼ cup (1 ounce) cornstarch, and ¼ teaspoon salt in large saucepan. Whisk in ¼ cup cream until smooth. Whisk in 2¼ cups whole milk. Cook over medium-high heat, whisking constantly, until thickened and large bubbles appear on surface, 2 to 3 minutes. Continue to boil for 30 seconds. Off heat, whisk in 1 cup bittersweet chocolate chips and 1 teaspoon vanilla until smooth. Pour into pie and smooth top. Place greased parchment paper directly on pudding surface and refrigerate until completely cool, at least 4 hours. (Pie can be refrigerated for 3 days.)

for the topping

Using stand mixer fitted with whisk attachment, whip 1 cup chilled cream, ¼ cup granulated sugar, and ½ teaspoon vanilla on medium-low speed until foamy, about 1 minute. Increase speed to medium-high and whip until just shy of stiff peaks, 1 to 2 minutes. Remove bowl and whisk attachment from mixer and whip by hand to desired texture. Spread whipped cream over pie filling, leaving ½-inch border around pie. Working gently, use spatula or spoon to create swirls and cowlicks over surface. Top with toasted pecans. Serve.