Chocolate Cupped Cakes with Coffee and Chicory

Heat the oven to 350°F. Spray the insides of 6 large oven-safe coffee cups or six 6-ounce ramekins with nonstick cooking spray and place on a rimmed baking sheet.
To make the cocoa sprinkle, whisk 1/4 cup of the sugar, the light brown sugar, and 2 tablespoons of the cocoa powder in a small bowl until most of the brown sugar lumps are broken up, and set aside.
Using a stand mixer (or in a large bowl if using a hand mixer), blend the butter and remaining sugar together on medium speed until the sugar looks like wet sand, about 2 minutes. Reduce the speed to low and add the cream and vanilla, mixing until well blended, using a rubber spatula to scrape the sides of the bowl as necessary.
Whisk the flour, the remaining cocoa powder, espresso powder, baking powder, and salt together in a large bowl and then add it to the butter mixture. Mix on low speed until a stiff dough comes together, then increase the speed to medium and beat for 15 seconds.
Divide the batter between the coffee cups, filling each one about half full, using the back of a spoon to press the batter into the cup. Top each with 2 tablespoons of the reserved cocoa sprinkle and then pour 21/2 tablespoons of coffee over the cocoa. Bake until the cakes soufflé up and the top of each cake is crusty and dry on top with no visible wet spots, about 55 to 60 minutes. Cool for at least 20 minutes before serving.
This cake is best eaten warm within a few hours of baking. If you have some left over the next day, you can heat it up in the microwave before serving to get its gooey quality back.