Preheat oven to 325°F. Lightly coat three 8-inch round baking pans with vegetable cooking spray and set aside.
In a medium saucepan combine the milk, chopped chocolate and cocoa powder. Heat on low and cook, stirring frequently, until all the chocolate is melted and the mixture is smooth. Remove from the heat and allow the mixture to cool for 5 minutes.
In a large mixing bowl whisk together the flour, sugar, baking soda and salt.
Add the oil, eggs and vanilla to the cooled chocolate mixture and whisk until smooth. Pour the chocolate mixture into the bowl with the flour and sugar. Using a stiff spatula or wooden spoon, stir until combined.
Pour the prepared batter into the baking pans. Bake for 23 to 28 minutes or until the center is firm when lightly pressed and a toothpick inserted in the middle comes out with a few crumbs attached.
Remove the cakes from the oven. Cool for 15 minutes then turn out onto a wire rack with the tops facing up. Using a skewer, prick each of the layers a few times. Mix together 2 tablespoons of the reserved cherry juice with the kirsch and drizzle or brush the mixture over the layers. Cool the cakes to room temperature. The cakes can be made 24 hours in advance. Once cooled, cover and refrigerate until needed.
To prepare the filling:
Gently fold together the drained sour cherries and the slightly warmed jam. Set aside.
To prepare the whipped cream:
Beat the room temperature cream cheese in a large cold mixing bowl until smooth. With the mixer running on low, slowly add the whipping cream until blended. Add the powdered sugar and vanilla and mix on low until incorporated. Turn the mixer to high and beat until stiff peaks form.
To prepare the ganache:
In a small saucepan combine the remaining cream and corn syrup. Bring the mixture to simmer over medium heat. Remove from the heat, add the chopped chocolate and cover with a lid. Set aside for 5 minutes. Whisk gently until smooth.
Place one cake layer on a serving platter or cake stand. Spread half the whipped cream mixture on top of the cake. Spoon half the cherries and jam over the whipped cream. Repeat with another cake layer, the remaining whipped cream and all the cherries and jam. Place the last cake layer on top then cover with the warm chocolate ganache allowing a small amount to drip decoratively down the sides. Once slightly set, garnish with fresh cherries on top.
Allow the cake to rest for about 30 minutes before serving or refrigerate until needed. Bring the cake to room temperature for 30 minutes before cutting. For clean cuts, run a thin, large knife under hot water then carefully dry the blade. The hot knife will slide through the chocolate ganache easily. Repeat as needed.
The chocolate cake recipe was adapted from Cook’s Illustrated and the filling was inspired by a recipe on BBC Good Food.