For the Pie Dough:ย In a food processor, pulse the flour, sugar, and salt five times. Add in the butter pieces and pulse until the butter is the size of small peas. (If using a stand mixer, mix everything on low speed until the butter is the size of small peas.)
Turn the dough out into a large bowl. Add the vodka slowly, using a rubber spatula to gently mix it in. Keep adding vodka until the dough is cohesive and can be patted together easily. Form the dough into a 1-inch-thick disk and wrap it in plastic wrap. Chill it in the refrigerator for at least 1 hour before using.
For the Pie: ย On a lightly floured surface, roll the chilled dough out into an 11-inch circle 1/4 inch thick. Fit it into a 9-inch pie plate. Crimp the edges and chill in the freezer while you melt the chocolate.
Over a saucepan of simmering water, stack a metal or glass bowl, making sure it fits snugly but the water doesn't touch the bottom. Put the chocolate, butter, cocoa, and the red pepper flakes in the bowl and stir until fully melted and smooth. Keep warm over low heat while you parbake the shell.
Preheat the oven to 375 degrees F.
To parbake the shell, cut a circle of parchment paper to fit over the crust and place it on top. Add dried beans or pie weights on top of the parchment. Bake for 12 minutes, then remove the beans and parchment, and bake the crust for another 3 minutes. The crust should be lightly golden brown on the edges and a pale tan on the bottom.
Reduce the oven temperature to 350 degrees F.
In a large bowl, whisk the eggs, sugar, milk, flour, vanilla, cinnamon, and salt. Add the chocolate mixture to the filling and mix until well blended.ย Pour the filling into the parbaked crust and bake until it's set and no longer jiggly in the middle, about 40 minutes. The crust will be a bit puffed and starting to crack.
Notes:
Liquored Pie Dough makes enough for two 9-inch crusts.