Preheat oven to 350F and line a 9×13-inch pan with foil for easier cleanup and spray with cooking spray; set aside.
Make brownies as directed (if there is a choice, use the ‘fudgy’ brownie directions), adding the water, oil, and eggs.
After the batter is mixed up, add the chocolate chips and stir to combine.
Turn batter out into prepared pan and bake for about 20 to 22 minutes, or until brownies are done; I prefer to err on the side of slightly underdone. Allow brownies to cool completely in pan.
After brownies have cooled, to a large bowl, add the cream cheese and beat with a handheld electric mixer until smooth.
Add 1/2 cup milk, pudding mix, and beat on low speed until smooth and combined.
Add the remaining milk and beat until combined and starting to thicken, about 4 to 5 minutes.
Add the whipped topping and beat until combined. Turn the mixture out over the brownies, smoothing it lightly with a spatula.
Cover pan and place in the fridge for at least 4 hours (overnight is even better) to set up.
Evenly drizzle the chocolate syrup over the top in a random pattern. Using a table knife, pull it through the chocolate sauce to create a ripple effect before serving. Brownies will keep airtight in the fridge for up to 5 days.