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To make brownies, preheat oven to 350 degrees.
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Grease a 9-by-13-inch baking pan.
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In a large saucepan, melt butter.
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Remove pan from heat and stir in chopped chocolate until fully melted.
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Stir in cocoa and sugar until combined.
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Slowly add eggs, whisking chocolate mixture constantly, then whisk in vanilla.
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Fold in flour and salt.
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Pour batter into prepared pan.
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Bake until just firm, about 25 minutes (do not overbake).
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Transfer pan to a rack to cool.
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If using spirits, prick holes in hot brownies and drizzle evenly over pan.
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In a large bowl, mix together granulated sugar, 3 tablespoons cocoa powder, cornstarch and salt.
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Whisk in 3/4 cup milk.
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In a large saucepan, bring remaining 1 cup milk and 1/2 cup cream to a boil over medium heat.
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Whisk hot milk mixture slowly into cocoa mixture.
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Return to saucepan.
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Cook over medium heat, whisking gently, until slightly thickened, about 2 minutes.
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(A simmering bubble or two is O.K., but do not let it boil.)
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In a medium heat-resistant bowl, whisk yolks.
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Whisking them constantly, very slowly dribble about half the cocoa-milk mixture into yolks until fully combined.
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Pour yolk mixture into saucepan with remaining cocoa-milk mixture, whisking constantly.
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Cook, whisking occasionally, over medium-low heat, until thickened, about 5 minutes.
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(Do not let mixture come to a simmer.
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If pan begins to steam thickly, remove from heat for a few moments and stir well before continuing.)
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Let cool slightly.
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Melt 5 ounces chopped chocolate with butter.
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Stir until smooth.
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Stir in vanilla.
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Cool 5 minutes, then fold into thickened egg mixture.
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Place plastic wrap directly against pudding (to prevent a skin from forming), and chill until set, about 3 hours.
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(Pudding and brownies can be made up to 5 days ahead, and refrigerated.)
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Just before assembling, in an electric mixer, beat remaining 2 1/2 cups cream with remaining 5 tablespoons cocoa powder and 1/4 cup confectioners' sugar until it forms soft peaks.
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Scrape down sides and fold in any excess cocoa or sugar.
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Cut brownies into 1-inch squares.
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Fit a layer of brownie squares in bottom of a 4-quart trifle, glass, or other bowl.
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Top with half the pudding, a third of the whipped cream, a third of the remaining chopped chocolate and a third of the raspberries.
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Repeat layering until all ingredients have been used.
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Serve immediately, or cover with plastic wrap and chill for up to 24 hours before serving.
