Triple Chocolate Tart with Boozy Whipped Cream
['"1/2 cup unsalted roasted almonds (see Cooks Notes)", 15 chocolate wafer cookies (such as Famous Chocolate Wafers; 4 ounces)', '2 tablespoons packed light brown sugar', '5 tablespoons unsalted butter, melted', '1 cup whole milk', '1/2 cup heavy cream', '1/2 cup chocolate stout, preferably double chocolate stout (to measure, tilt cup and pour it slowly down side of a liquid measuring cup, then let foam dissipate or skim it off)', '2 tablespoons packed light brown sugar', '2 tablespoons unsweetened cocoa powder', '2 tablespoons cornstarch', '2 ounces good-quality bittersweet chocolate (60 - 62% cacao), finely chopped', '1/2 teaspoon pure vanilla extract', '1 cup chilled heavy cream', '2 tablespoons bourbon', '2 teaspoons sugar', '1/4 teaspoon pure vanilla extract', '9-inch tart pan (1-inch deep with removable bottom) or 9-inch springform pan', 'Chocolate shavings or cocoa powder', 'optional']
Preheat oven to 350°F with rack in middle.
Pulse almonds with cookies and sugar in a food processor until almonds and cookies are finely ground.
Add butter and pulse to combine, then press evenly onto bottom and up side of tart pan or 1-inch up side of springform pan (a dry measuring cup with a smooth bottom is very useful for pressing crumbs into an even layer).
Bake until set, 15 minutes. Cool on a rack 1 hour.
Whisk together milk, cream, stout, sugar, cornstarch, and cocoa in a medium saucepan and bring to a boil over medium heat, whisking constantly, then briskly simmer, whisking constantly, 2 minutes.
Remove from heat and whisk in chopped chocolate and vanilla until smooth.
Pour chocolate custard into cooled tart shell and cover surface with plastic wrap or wax paper (to prevent a skin from forming) and chill until set, about 3 hours.
Beat cream, bourbon, sugar, and vanilla in a bowl with an electric mixer just until stiff peaks form. Spread whipped cream decoratively on top of pie.
Garnish with chocolate shavings or dust with cocoa powder, if desired.
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