Line a loaf pan with plastic wrap leaving 2 inches of overhang on each side.
Place 1 cup of fresh raspberries in the bottom of the loaf pan and freeze for 30 minutes until the berries have firmed up a bit.
Spread the raspberry sorbet in an even layer over the partially frozen berries making sure that the layer is level.
Create a cookie layer by laying cookies in rows of 2, slightly overlapping so that no sorbet is showing.
Spread the softened vanilla bean ice cream over the cookie layer and smooth it out into an even layer.
Top with an additional layer of cookies then cover with plastic wrap and freeze for 6-8 hours or overnight.
Right before serving place the chocolate chips and shortening in a microwave-safe bowl and heat in 15-20 second increments at 50% power, stirring in between each cook time until smooth, set aside.
Remove the plastic wrap from the top of the pan, invert onto a serving dish and remove the rest of the plastic wrap. Top with the remaining raspberries and drizzle with the melted chocolate. Serve immediately.