Using a stand mixer with a whisk attachment, whip together the heavy cream, powdered sugar, and vanilla extract until stiff peaks form (approximately 5-7 minutes). Once done, set the whipped cream aside in a separate bowl.

In a cleaned stand mixer bowl, whip the softened cream cheese until fluffy (about 30 seconds). Next, add the sweetened condensed milk, and beat until smooth. Gradually incorporate the dry banana pudding mix and then stream in the milk, mixing until fully combined.

Gently fold two-thirds of the whipped cream into the pudding mixture until no streaks remain. Set this aside for assembling.

Lightly grease a 9x13 inch baking dish. Create even layers of Nilla wafers, sliced bananas, and half of the pudding mixture. Repeat for another layer, then top it all off with the remaining whipped cream.

Cover your masterpiece with plastic wrap and refrigerate for at least 8 hours, or preferably overnight. Before serving, crush any remaining Nilla wafers and sprinkle them over the top.