Heat oven to 350°F. Place paper baking cup in each of 24 regular-size muffin cups. Make and bake cake as directed on box for cupcakes, using water, oil and eggs. Cool completely. With melon baller, scoop out center of each cupcake, scooping almost to bottom of cupcake.
In large bowl, beat pudding mix, milk and vanilla with wire whisk about 2 minutes or until well blended. Let stand 5 minutes or until thickened. Fold in whipped topping. Spoon into 1-quart resealable food-storage plastic bag. Cut 3/8-inch tip off 1 bottom corner of bag. Insert tip of bag into top of each cupcake and squeeze bag to fill cupcake with pudding.
In medium bowl, place chocolate chips. In 1-quart saucepan, heat whipping cream just to boiling; pour over chocolate chips. Let stand 3 to 5 minutes until chocolate is melted and can be stirred smooth. Dip tops of cupcakes in chocolate mixture.