Prepare the pan: Trace and cut out a 9-inch circle from parchment paper and fit it into the bottom of a 9-inch springform pan.
Cut out a 3- by 27-inch strip of parchment and fit around the inside of the pan. Tape to secure parchment paper and set aside.
Assemble the cake: Cover the bottom of the pan with a single layer of pound cake slices and spread the ice cream evenly over the cake. Freeze until ice cream hardens — about 25 minutes. Spread 2 cups sorbet over the ice cream followed by another layer of pound cake slices.
Return cake to the freezer for 10 minutes. Combine the raspberries and the Chambord together in a small bowl. Remove the cake pan from freezer and place the berries evenly over the cake.
Top with a final layer of pound cake and the remaining sorbet. Wrap tightly with plastic wrap and freeze until firm — at least 4 hours.
In a large bowl, whisk together the pudding mix and 3 cups milk until smooth and well combined. Stir in the chopped chocolate. In another medium bowl, whisk to combine Cool Whip with 1/4 cup milk. In another small bowl, whisk to combine cherry preserves and 2 tablespoons water.
Spoon a tablespoon of the pudding into each popsicle mold and top with a spoonful of whipped topping. Pour the pudding mixture halfway up the molds and add a spoonful of preserves. Top off each with remaining pudding, insert popsicle sticks and freeze until firm, at least 6 hours or overnight.
Unmold and garnish with shaved chocolate and fresh cherries.
Make the base: In a medium mixing bowl, use an electric mixer to combine peanut butter and sugar until smooth. Add milk and mix on low until sugar is dissolved- a full two minutes. You don’t want to be tasting crunches of sugar in your ice cream, so give it a chance to dissolve. Mix in heavy cream and vanilla and beat until well combined and smooth.
Process the ice cream: Turn on your ice cream machine, pour the base in the freezer bowl, and let mix until thickened, about 25 to 30 minutes. A couple of minutes before you’re ready stop the mixing, add in the chopped peanut butter cups. The ice cream will be a soft-serve consistency. You can eat it right away, or freeze to eat later. If you freeze it for later, it will be more ice-cream-scoopable. Let it sit out for a few minutes before you try to scoop it.