In a small saucepan over low heat, combine the chocolate chips and heavy cream. Stir occasionally, until the chips are melted and smooth. This may take up to 10 minutes, but keep the heat on low or a little higher than low.
Once melted, remove the pan from the heat and allow it to cool on the counter for 15 minutes.
Once the chocolate is cool, combine the melted chocolate and softened cream cheese in a mixing bowl. Beat using an electric mixer until the mixture is smooth and no lumps remain. Refrigerate for 20 minutes.
Crush the graham crackers. I like to break them up and put them inside 2 ziploc bags (to ensure the crumbs don’t get out) and use my rolling pin to crush them. Once crushed, add 2 tbsp of graham cracker crumbs to each glass.
Transfer a little bit of the cheesecake mixture to a piping bag and pipe the cheesecake into each glass. Refill the pipping bag as needed. *You could just spoon the cheesecake into the glasses, but I think piping it makes the filling like a little fancier.
If you plan to serve them later, refrigerate and be sure to cover the glasses with plastic wrap or tin foil.