In a saucepan, melt sugar with water over medium heat until it turns a golden amber color; pour immediately into the flan mold and swirl to coat the bottom.

Blend sweetened condensed milk, evaporated milk, cocoa powder, melted chocolate, and vanilla until smooth; set aside.

In a clean blender, combine softened cream cheese, eggs, whole milk, sugar, and vanilla until the mixture is smooth and well combined.

Carefully pour the chocolate fudge mixture over the hardened caramel in the mold, then slowly pour the cream cheese flan mixture over the chocolate layer.

Place the flan mold into a larger roasting pan, then fill the roasting pan with hot water halfway up the sides of the flan mold; bake at 350°F (175°C) for 70-75 minutes or until set.

Remove the flan from the water bath and cool completely at room temperature, then refrigerate for at least 6 hours or overnight before inverting onto a serving plate.