For the crust: Pulse the flour, shortening, granulated sugar, vinegar and salt in a food processor until it looks like fine meal. Add the butter, and pulse until it is in pea-size pieces. Sprinkle in 2 tablespoons of the ice water, and pulse until the dough begins to come together. Pinch the dough with your fingers; if it doesn't hold together, add up to 2 teaspoons more ice water, 1 teaspoon at a time, pulsing and checking the dough after each addition. Wrap the dough tightly, and refrigerate until firm, at least 1 hour or preferably overnight.
Position a rack in the center of the oven, and preheat to 375 degrees F. Roll the dough into a disc 11 to 12 inches wide on a lightly floured surface. Sandwich the dough between pieces of parchment or wax paper on a baking sheet, and refrigerate for at least 10 minutes. Lay the dough in an 8-inch pie pan so it extends about 1/2 inch beyond the edge of the pan. Fold the outer edge of the dough up under itself, and crimp decoratively between your index finger and forefinger. Poke the dough all over with a fork, and refrigerate for 10 minutes more. Line the pie crust with parchment or foil, fill with pie weights or beans and bake until the dough appears dry to the touch, about 20 minutes. Remove the foil and weights, and continue cooking the crust until it's light brown and cooked through, 5 to 7 minutes more. Let the crust cool completely on a wire rack.
For the filling: Reduce the oven temperature to 350 degrees F. Whisk the heavy cream, granulated sugar, yolks, egg, bourbon, zest, cherry juice and salt in a medium bowl until smooth. Place the cooled crust on a rimmed baking sheet, and pour the custard into the crust. To avoid overbrowning, cut 2 strips of aluminum foil to wrap over the crust edges. Carefully transfer the pie to the oven, and bake until the custard is set but still has a slight jiggle, 50 to 60 minutes. Let the pie cool completely on a wire rack, about 4 hours. If serving the next day, let cool completely, then wrap and refrigerate overnight.
For the bourbon whipped cream: Beat the confectioners' sugar and bourbon in a large bowl with an electric mixer on low speed. Add the heavy cream, increase the speed to medium-high and beat until firm peaks form, about 1 minute.
Put six 2-tablespoon dollops of the whipped cream around the pie, and top each with a cherry. Twist the orange slices, and place them in between the whipped cream dollops. Serve the pie with the remaining whipped cream.
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