Step 1

Make the cake batter:

Step 2

Preheat the oven to 350 F and line a cupcake pan with paper baking cups.

Step 3

In a large bowl, using a whisk, mix together the butter and sugars, flexing your muscles for about 2 minutes, until the mixture is light, fluffy and fully combined. Whisk in the egg, stirring to aerate and combine it, about 1 minute. Whisk in the oil, milk, vanilla and vinegar, and mix vigorously for another 2 minutes, to yield a looser, smoother mixture.

Step 4

Add the flour, cocoa powder, baking powder and salt into the mixing bowl. Ditch the whisk and, with a sturdy spatula, toss together only the dry ingredients on top first, before truly stirring them into the wet ingredients below. Mix until everything is just combined.

Step 5

Make the cheesecake filling:

Step 6

In a small bowl, with a cereal spoon or a small but sturdy spatula, mix the cream cheese, sugar, vanilla and salt together, and stir until the mixture is smooth and luscious, about 1 minute.

Step 7

To assemble:

Step 8

Divide the cake batter evenly among the cupcake cavities, filling each two-thirds full.

Step 9

Divide the cheesecake filling equally across the tops of the cake batter with a spoon, then press the cheesecake filling deeper down into the batter, nearly hitting the bottom, but stopping short. The cupcake cavity will be three-quarters full in total. Sprinkle chocolate chips evenly atop the cupcakes.

Step 10

Bake for 16 to 18 minutes, until the chocolate batter poufs up around the cheesecake portion, which will set in the center. Cool the cupcakes completely in the pan before checking out those chocolatey bottoms!