Lightly grease a 9x13 baking dish with cooking spray; set aside.

In the bowl of a stand mixer, add in the heavy whipping cream, confectioners' sugar, and vanilla extract. Using the whisk attachment, whip until stiff peaks form, about 5-7 minutes. Remove the whipped cream to a separate medium bowl and set aside.

In the wiped-out stand mixer bowl, add the cream cheese and, using the same whisk attachment, whip it until fluffy, about 30 seconds.

Add the sweetened condensed milk and beat until smooth, ensuring no lumps of cream cheese remain, stopping to scrape the bottom and sides of the bowl as needed.

Add the dry pudding mix and mix well, then slowly stream in the milk and mix until fully combined.

Add 2/3 of the whipped cream to the pudding mixture and fold it in gently until fully combined, with no whipped cream streaks remaining. Set aside.

In the prepared pan, place an even layer of Nilla Wafers, followed by an even layer of sliced banana coins. Top with half of the pudding mixture and spread evenly.

Repeat with another layer of Nilla Wafers, sliced bananas, and the remaining pudding layer, spreading it evenly. Top with the remaining 1/3 of the whipped cream.

Cover and refrigerate for at least 8 hours or overnight.

Just before serving, crush any remaining Nilla Wafers and sprinkle over the top.