For the Pudding:
2 and 1/2 tablespoons (23 grams) cornstarch
1/4 cup (50 grams) granulated sugar
1 tablespoon brown sugar
2 cups (460 grams) whole milk
5 ounces (142 grams) 60% bittersweet chocolate, coarsely chopped
1 teaspoon pure vanilla extract
For the Cupcakes:
1 and 1/4 cups all-purpose flour (150 grams)
1 cup unsweetened non-alkalized (natural) cocoa powder (112 grams)
1 teaspoon (5 grams) baking soda
1 and 1/2 (6 grams) teaspoons baking powder
1/2 teaspoon salt
4 tablespoons (63 grams) canola oil
1/2 cup (113 grams) unsalted butter
3 ounces bittersweet chocolate (60%), finely chopped
1 teaspoon espresso powder
1 cup (198 grams) granulated sugar
3/4 cup (142 grams) light brown sugar, packed
2 large eggs plus 1 large egg yolk, at room temperature
2 teaspoons vanilla
1 cup full fat sour cream
1 cup hot coffee OR hot water
For the Frosting:
6 ounces bittersweet chocolate (62%), finely chopped
4 ounces unsweetened chocolate, finely chopped
3 sticks (340 grams) unsalted butter, softened
2 and 1/2 cups (283 grams) confectioners’ sugar, sifted
2 teaspoons vanilla extract
For the Pudding (make ahead, anywhere from 2 hours to 3 days):
- In a small, heavy bottomed saucepan, combine the cornstarch and both sugars. Gradually pour in the milk, adding it a little bit at a time, and whisking well to ensure no lumps form in the mixture.
- Cook over medium heat, stirring constantly, until the mixture thickens and can coat the back of a spoon, about 10 minutes.
- Add the chopped chocolate and continue to cook, stirring often, for about 4 minutes, or until the pudding is smooth and very thick.
- Remove from heat and stir in the vanilla. Pass the mixture through a fine-mesh strainer into a large serving bowl.
- Place plastic wrap on top of the pudding and smooth it gently against the surface. Refrigerate for at least 2 hours, or up to 3 days.
For the Cupcakes:
- Preheat oven to 350 degrees (F).
- Line two 12-cup muffin tins with cupcake liners. Spray lightly with non-stick baking spray, and set aside.
- In a large bowl, sift together the flour, cocoa powder, baking soda, baking powder, and salt. Set aside.
- Combine the oil, butter, and chocolate together in a large bowl. Use a double boiler or heat in the microwave, in 30 second increments, stirring between increments each time, until the butter and chocolate are completely melted. Stir in the espresso powder. Set aside and cool while you assemble the other ingredients.
- In a large bowl, combine both sugars, eggs, egg yolk, and vanilla and beat until smooth and well combined.
- Gradually add in the melted chocolate mixture, adding a little bit at a time and whisking constantly.
- Gently fold in the flour in 3 additions, alternating with the sour cream, beginning and ending with the flour. Mix gently and stop when you can still see the lightest trail of dry ingredients.
- Pour in the hot coffee (or water) and let it sit for 30 seconds, then fold it into the batter until combined.
- Fill each cupcake liner so that they’re 2/3 full with batter. Bake, one tray at a time, for 16 to 18 minutes, or until the cupcakes have puffed up and a toothpick (or cake tester) inserted in the middle of a cupcake comes out clean, or with a few moist crumbs attached.
- Allow cupcakes to cool completely before frosting.
For the Frosting:
- Place both chocolates in a microwave-safe bowl. Use a double boiler or heat in the microwave, on low power, in 30 second increments, stirring between each increment, until the chocolate is completely smooth and melted. You may also do this in a double-boiler. Set aside and cool until tepid.
- In the bowl of a stand mixer fitted with the paddle attachment or in a large bowl using a handheld electric mixer, beat the butter until completely smooth.
- On low speed, add in the confectioners’ sugar, a little bit at a time, beating until each addition has been completely incorporated into the butter before adding more. Once all of the sugar has been added, increase speed to medium-high and beat for 3 minutes.
- Decrease the speed back to low and beat in the vanilla extract. Then slowly pour in the cooled melted chocolate and continue mixing until well combined, tuning the mixer off and scraping down the sides and bottom of the bowl as needed.
- Once all of the chocolate has been added, increase the speed back to medium-high and beat for 2 minutes. Set aside for 30 minutes to firm up, or up to 3 hours. Do not refrigerate (the chocolate will seize and render the frosting impossible to spread).
- Using a paring knife, cut out a 1/2″ inch cone shaped hole in the middle of each cooled cupcake. The hole should stop about 1/4″ from the bottom of the cupcake, to avoid breaking the base. Set all of the cupcake scraps aside!
- Scrape the chilled pudding into a large piping bag fitted with a medium piping tip.
- Pipe the filling into the middle of each cupcake cavity, filling it all the way to the top.
- Next, scrape your frosting into a piping bag fitted with an open star piping tip. Pipe the frosting on top of each cupcake, making sure the pudding is completely covered.
- Crumble up the cupcake scraps into fine crumbs and sprinkle a generous amount on top of each cupcake.
Serve at once, or store in the fridge until needed. Cupcakes are best served the day they are made, but will keep, stored in the fridge, for 2 days.