Beat 3 cups of heavy whipping cream in a stand mixer with whisk attachment on medium high speed until cream forms. About 2-3 minutes.
Add powdered sugar and vanilla and mix to combine and fluff until soft peaks form. About 1 minute.
Line loaf pan or Tupperware with plastic wrap. Leave enough plastic wrap over the sides to be able to cover cake later.
Cover the bottom with a thin layer or whipped cream.
Start sandwiching cookies together with a spoonful of whipped cream. Once you have about 3-4 cookies together, stand up in 4 rows of about 8-12 cookies in the loaf pan.
Cover the entire cake with whipped cream. Save remaining whipped cream in the fridge.
Cover cake with plastic wrap and place in fridge for at least 4 hours (or overnight).
Unwrap and turn cake out onto serving platter.
Spread remaining whipped cream over top of cake.
Top with sprinkles/cookie crumbs/chocolate shavings if desired.
Place in freezer for 30 minutes to set before serving!