Makes 1 cake, to serve 16 to 20.
- 18 Tbsp. unsalted butter at room temperature, plus more for greasing
- 2 1/4 cups packed dark brown sugar
- 3/4 cup granulated sugar
- 4 large eggs, at room temperature
- 1 large egg yolk
- 2 1/4 cups red wine
- 1 Tbsp. vanilla extract
- 3 cups plus 2 Tbsp. all-purpose flour
- 1 1/2 cups Dutch-process cocoa powder
- 3/8 tsp. baking soda
- 1 1/2 tsp. baking powder
- 3/4 tsp. ground cinnamon
- 3/4 tsp. salt
- 24 ounces cream cheese (three 8-ounce boxes), at room temperature
- 3/4 cup (1 1/2 sticks) butter, at room temperature
- 2 tsp. vanilla extract
- 3 1/2 cups confectioners' sugar
Active time: 30 minutes
Total time: 1 hour
To make cake: Preheat oven to 325°. Line the bottom of three 9 round cake pans with parchment paper. Grease parchment and sides of pan. Place butter in a large bowl. Using an electric mixer, cream butter on medium speed until smooth. Add brown and granulated sugars and beat until fluffy, about 3 minutes. Add eggs and yolk and beat until incorporated, then add red wine and vanilla. (Don't worry if the batter looks a little uneven and grainy.)
In a medium bowl, mix flour, cocoa powder, baking soda, baking powder, cinnamon, and salt. Sift dry mixture over wet ingredients. Mix until 3/4 combined, then fold in remaining dry mixture with a rubber spatula.
Divide batter among prepared pans. Bake 25 to 30 minutes, or until a cake tester inserted into the center of each layer comes out clean. The top of each cake should be shiny and smooth. Cool in the pan 10 minutes, then remove cakes from pans and let cool completely on a rack. (If cakes have domed a bit and you want even layers, trim tops using a long serrated knife held horizontally.)
To make frosting: In a medium bowl, use an electric mixer to beat cream cheese and butter until smooth. Mix in vanilla, then gradually stir in confectioners' sugar.
To frost cake, place one layer on a cake stand or plate and spread with 1 cup frosting. Repeat with next 2 layers and spread top and sides with remaining frosting.
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