In a medium mixing bowl, whisk together 2 cups of milk and 1 cup of room temperature cool whip until smooth. Repeat in a second mixing bowl.
Add the chocolate pudding into one bowl of milk and the vanilla into the other bowl. Whisk until just combined.
Working quickly, pour the pudding into the molds. If you want striped or marbled flavors, alternate chocolate and vanilla in the molds. The pudding will thicken quickly, so work fast. If it thickens before you finish, just spoon in the pudding, gently tapping your molds against the counter so the pudding evens out in the molds and fills the bottom. Be careful not to fill the molds all the way to the top so the mixture has room to expand as it freezes.
Insert the sticks and freeze for at least 4 hours.
When you're ready to consume, just run the mold under running water for 15 seconds or so to loosen the pops from the mold.
If you want to add toppings, remove the pops from the molds and let them sit at room temperature for 3 to 5 minutes or until they just begin to soften. Press your toppings into them then place them on a parchment lined sheet pan and freeze for an additional 20 or 30 minutes before serving.
Notes
The number of pudding pops you get will vary based on the size of your mold and will also alter the nutritional information. We did base ours on making 16 for the recipe.