Beat the eggs and milk together until it becomes frothy. In a medium bowl, mix together the sugar, flour, cocoa powder, salt, and baking powder together. Mix the dry ingredients into the wet ingredients and mix until there are no lumps.
In a large cast iron skillet (I used a 12 inch skillet) heat about 2 inches of canola or vegetable oil until it reached about 375F degrees. It’s okay if it’s a little under as long as it is no less than 370F.
Pour your batter either into a funnel or piping bag with a round tip and swirl the batter into the oil in a mostly random circular motion. I like to kind of mimic the shape of a spider web. Cook the funnel cake on one side for a minute before flipping and cooking for another 45 seconds to a minute.
Place the funnel cakes on a wire rack covered in paper towels.
While you are cooking the funnel cakes, place the cherries and sugar into a medium saucepan and heat on medium-high heat until the juices release and form a syrup. Turn off the heat and stir in the vanilla.
Use a chilled bowl and wire whisk to beat the heavy cream until soft peaks form. Beat in the powdered sugar. You may optionally reserve a tablespoon of powdered sugar to put over your funnel cakes.
Top the funnel cakes with the cherries and then top with a generous dollop of heavy cream. Drizzle a bit of the cherry juice over the whipped cream if desired.
Best if eaten immediately, but if you must wait, do not assemble until ready to serve. Funnel cakes are best served warm, but you may keep in an airtight container up to 24 hours.