My mom came to the United States from Colombia when she was 16 years old. She married at 17, had her first child by 18 and quickly needed to find her way in the kitchen. New American convenience foods were a novelty to her, and we were occasionally treated to pudding from the store. My brother loved chocolate pudding so much that, once my mom became more fluent in the kitchen, she decided to try making it from scratch. Chocolate pudding became one of our favorite childhood treats, and it's still one that makes me remember my mom and all the fun and nostalgia of my childhood in the 1960s and '70s. - Claudia Sidoti, Manager, Test Kitchen
Whisk the milk, granulated sugar, cocoa and cornstarch constantly in a nonreactive medium saucepan over medium-high heat until the cocoa has fully dissolved and the mixture starts to simmer, about 8 minutes. Reduce the heat to medium, and continue to cook, whisking, until the mixture thickens to the consistency of a light gravy, 6 to 7 minutes more. Stir in the chopped chocolate, vanilla and a pinch of salt and continue to cook, whisking, until the chocolate has melted and the pudding is thick and creamy, about 2 minutes more. Remove the pudding from the heat, add the butter and stir until the butter has melted.
Divide the pudding evenly into six 6- to 8-ounce ramekins or glasses. Cover with plastic wrap, and refrigerate for 4 hours or overnight until cold and fully set.
Before serving, pour the cream and confectioners' sugar into a chilled medium bowl. Whip the cream with a whisk or an electric mixer until soft peaks form, 2 to 3 minutes. Top each pudding with a dollop of whipped cream and chopped-chocolate garnish if using.
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