In a medium mixing bowl, combine the vanilla wafer crumbs (2 1/2 cups) and sugar (1/4 cup). Add the butter (1/2 cup) and mix well. Press firmly onto the bottom and up the sides of a 9-inch pie plate. Bake for 10 to 12 minutes or until golden brown. Remove from oven, and cool completely before adding filling (about 1 hour).
Make the Filling:
In a medium, heavy-bottomed saucepan, combine sugar (1/2 cup plus 2 tablespoons), cornstarch (1/4 cup), and salt (1/8 teaspoon). Whisk in egg yolks (5), Gradually add milk (1 1/2 cups) and cream (1 cup). Cook over medium heat, bringing to a gentle boil, whisking constantly until mixture thickens 8-10 minutes. Continue to gently simmer for 1 minute, lowering heat as necessary, and stirring constantly. Remove from heat. Whisk in vanilla (2 teaspoons), butter (2 tablespoons), and brandy (1 teaspoon).
Pour the filling into a bowl. Place plastic wrap directly on the surface of the filling to prevent a skin from forming. Cool for about 30 minutes or until the filling is warm but no longer hot.
Pour half of the warm filling into the cooled crust. Peel and slice the bananas into 1/2-inch slices and layer on top of the filling. Pour the remainder of the filling over sliced bananas. Place a clean sheet of plastic wrap directly on the top surface of the filling. Refrigerate pie until completely chilled, at least 3 hours.
Make the Topping:
Whip the heavy cream (2 cups) in a chilled bowl until soft peaks form. Add powdered sugar (3 tablespoons) and vanilla (1/2 teaspoon); continue to whip until peaks are just stiff. Spread whipped cream over the topping and shape decoratively into a mound. Refrigerate until ready to serve.
Notes
Press the crust like you mean it. Use the flat bottom of a measuring cup to really pack those crumbs into the pie plate—this is the difference between a crust that slices cleanly and one that crumbles when you serve.
Want the smoothest custard possible? Strain it. If you want that ultra-luxury, diner-style texture, pour the hot custard through a fine mesh sieve before cooling. It catches any tiny bits and makes the filling unbelievably silky.
Seal the bananas in custard. Bananas brown when air hits them—so your best defense is coverage. After the top custard layer goes on, gently press with a spatula to encourage custard down into the little gaps between banana slices.
Try the “towel tap” trick for prettier layers. Set a dish towel on the counter and gently tap the pie plate a few times to help the custard settle into any small voids around the banana slices.
Chill your tools for whipped cream that behaves. Pop your metal bowl + beaters in the freezer for 10–15 minutes. Cold tools + cold cream = faster whipping and a thicker, fluffier topping.
Stop at just stiff peaks. Whip on medium speed and stop when peaks stand tall but still look smooth. Go too far and the whipped cream turns grainy… and a little further and you’re making butter.