Ingredients

  • 1 cup flour, plus 1 1/2 tablespoons
  • 1/4 teaspoon salt
  • 3/4 teaspoon sugar, plus 3/4 cup
  • 1/2 cup vegetable shortening
  • 2 tablespoons ice water
  • 1 cup plus 2 tablespoons semi-sweet chocolate chips
  • 3/4 cup heavy cream
  • 2 1/4 cups pecan pieces
  • 6 eggs, beaten
  • 3/4 cup (packed) light brown sugar
  • 1/4 cup plus 2 tablespoons cane syrup (or molasses)
  • 1 cup, plus 2 tablespoons light corn syrup
  • 3/4 teaspoons vanilla extract
  • 1/8 teaspoon salt
  • 6 tablespoons butter, melted
  • 3 tablespoons (or more) Bourbon whiskey
  • Vanilla Bean Ice Cream, recipe follows
  • 3 cups heavy cream
  • 2 cups milk
  • 1 vanilla bean, split lengthwise
  • 12 large egg yolks
  • 1 cup sugar

Method

  • Crust: Combine 1 cup of the flour, salt and 3/4 teaspoon of the sugar in a mixing bowl.
  • Add the shortening and work it in your hands until the mixture resembles coarse crumbs.
  • Add the water, a little at a time, and work it in with your hands.
  • Add only as much as you need for a smooth ball of dough.
  • Wrap the dough and refrigerate for at least 30 minutes.
  • Remove the dough from the refrigerator and place it on a lightly floured surface.
  • Roll out the dough on the floured surface into a circle about 12 inches in diameter and 1/8-inch thick.
  • Gently fold the circle of dough in half and then in half again so that you can lift it without tearing it, and unfold into a 9-inch pie pan.
  • Refrigerate for 1 hour, or until ready to fill.
  • Filling: Put the chocolate chips in a small bowl.
  • Heat the heavy cream in a small saucepan until just boiling, then pour over the chocolate chips.
  • Stir until the chocolate has melted and a smooth sauce has formed.
  • Set aside and reserve for the pie.
  • Preheat the oven to 375 degrees F.
  • Remove the pie shell from the refrigerator, and spread the pecan pieces evenly on the bottom.
  • Combine the eggs, the remaining 3/4 cup sugar, brown sugar, cane syrup, corn syrup, vanilla, salt, butter, and the remaining 1 1/2 tablespoons flour in a mixing bowl.
  • Mix well.
  • Pour the mixture over the pecans.
  • Bake for about 1 hour, or until the filling sets and the pastry is nicely browned.
  • When you remove the pie from the oven, drizzle the whiskey over-top the pie.
  • Pokes holes into the pie filling with the tip of a sharp knife so the bourbon has a route to travel.
  • Cool for 10 minutes, and then pour the chocolate mixture over top the pie.
  • Let the pie set in the refrigerator for 10 minutes for the chocolate to harden, then slice, and serve the pie with the vanilla bean ice cream.
  • The pie may also be served warmed briefly in a microwave.
  • Combine the cream and 1 cup of the milk in a large heavy saucepan.
  • Scrape the seeds into the cream mixture and add the bean pod.
  • Bring to a gentle boil over medium heat.
  • Whisk the yolks and sugar in a medium bowl.
  • In a slow and steady stream, whisk 1 cup of the hot cream mixture into the egg mixture.
  • Gradually whisk the egg mixture back into the saucepan.
  • Stir constantly over medium-low heat until the mixture thickens enough to coat the back of a spoon and reaches 170 degrees F on an instant-read thermometer, about 5 minutes.
  • Strain through a fine- mesh sieve into a heatproof medium bowl.
  • Stir in the remaining 1 cup milk into the ice cream base and cover with plastic wrap, pressing the wrap against the surface of the custard to prevent a skin from forming.
  • Refrigerate until well chilled, at least 2 hours.
  • Pour the chilled custard into an ice cream machine.
  • Churn according to the manufacturer's instructions.
  • Pack into an airtight container and freeze until ready to serve.