Steps:
- Make pudding filling: Whisk together cornstarch, 1/3 cup sugar, cocoa powder, and salt in a 2-quart heavy saucepan, then gradually whisk [tips alert!] in milk. Bring to a boil over medium heat, whisking constantly, then boil, whisking, two minutes (mixture will thicken). Remove from heat and whisk in chocolate and vanilla until smooth. Pour filling into cooled shell and chill, its surface covered with wax paper (if you want to prevent a skin from forming), until cold, at least two hours. Just before serving, beat cream with remaining two tablespoons sugar until it just holds soft peaks. Spoon onto pie and garnish with bittersweet chocolate shavings, if you're feeling fancy. Do ahead: Pie dough can be made and chilled up to two days. Pie, without whipped cream, can be chilled up to one day before serving. Whipped cream is best added at the last minute, however, I did find that ours held up surprisingly well for a day (so far), if you feel like winging it. * Detour! This is where I admit that I for reasons both lengthy and boring, I really loathe working with pie weights and use a different technique to blind bake pie and pastry shells. Instead, I freeze my rolled-out shells for 20 to 30 minutes until solid, press a piece of buttered foil, buttered side down, very tightly against the frozen shell and blind bake it according to regular directions. When it is time to remove the weights, I carefully pull back the foil, and press any part of the crust that has bubbled up gently back with the back of a spoon and continue baking the shell. Try it!
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