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To make the Chocolate Pudding: Combine 1 cup milk with 2 tablespoons sugar in a small saucepan and bring to just under a boil.
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In a mixing bowl, combine remaining sugar with salt, cocoa, and cornstarch.
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Whisk in remaining 1/2 cup unheated milk.
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Gradually whisk in hot milk and place entire mixture back into the saucepan.
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Heat, over medium heat, stirring, until mixture thickens and just starts to bubble.
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Whisk in egg and egg yolk and cook, stirring, for 30 seconds.
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Remove from the heat and whisk in chopped chocolate and butter.
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When both are melted, strain pudding through a fine-mesh strainer, and cool.
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Cover with plastic and reserve in refrigerator.
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To make the Cake: Preheat oven to 350 degrees F. Lightly butter 2 (8-inch) cake pans and line with parchment.
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Butter the parchment and flour pans, shaking out the excess.
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Sift together flour, cocoa, baking soda, baking powder, and salt.
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Reserve.
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In a mixer with a whip attachment, beat eggs and sugar until thick and lemon-colored.
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Beat in vegetable oil.
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Alternately add dry ingredients with buttermilk, scraping the bowl once or twice.
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Add the coffee and vanilla to form a thin batter.
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Divide between prepared cake pans.
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Bake until a toothpick inserted in the center of a cake comes out clean, about 40 to 45 minutes.
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Cool in pan for 15 minutes.
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Invert onto cooling racks, peel off paper and cool completely.
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When cool, split each cake in half with a serrated slicing knife.
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Reserve 1 layer for another use.
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Spread bottom layer with half of the reserved Chocolate Pudding.
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Place second layer on top and spread with remaining pudding.
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Top with last cake layer.
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To make the Icing: Over a double boiler, melt chocolate with butter.
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Remove from heat, whisk in brewed coffee, corn syrup, and vanilla.
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Place icing over an ice bath and chill, whisking often until the mixture is of soft but a spreadable consistency.
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Working quickly, ice the sides and top of cake.
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In a food processor, pulse the cookies into crumbs.
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Press the crumbs onto sides and top of cake.
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Serve cake at room temperature.
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If holding for more than 2 hours, store in refrigerator for up to 48 hours, but bring to room temperature before serving.
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Serving Suggestion: Blackout cake is meant to be served simply, on its own.
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If you want to dress individual plates, perhaps add a drizzle of fudge sauce and a sprinkle of cocoa powder.