Chill your tools. Place your mixing bowl and whisk or beaters in the freezer for 10 minutes.
Cold tools help the cream whip faster and hold better.
Make the pudding base. In a large bowl, whisk the instant pudding mix with evaporated milk (or whole milk) until smooth and thick, about 2 minutes. Set aside to finish thickening.
Whip the cream. In the chilled bowl, beat heavy cream with sugar (if using) and 1 teaspoon vanilla until medium-stiff peaks form. Do not overbeat.
Set aside.
Beat the cream cheese. In another bowl, beat softened cream cheese with sweetened condensed milk, remaining 1 teaspoon vanilla, and a pinch of salt until silky and lump-free.
Combine the creams. Fold the prepared pudding into the cream cheese mixture until smooth. Then gently fold in the whipped cream in two additions. Keep it light—those air bubbles make it fluffy.
Prep the bananas. Slice bananas into 1/4-inch rounds.
If you’re worried about browning, lightly brush or toss slices with lemon juice. Don’t overdo it or you’ll taste the citrus.
Layer it up. In a 9x13-inch dish (or a trifle bowl), add a layer of vanilla wafers. Top with half the banana slices.
Spoon on half of the fluffy pudding mixture and smooth it out.
Repeat. Add another layer of wafers, the remaining bananas, and the rest of the pudding mixture. For a pretty finish, decorate the top with crushed wafers or whole wafers around the edges.
Chill. Cover and refrigerate for at least 4 hours, preferably overnight. The wafers soften and the flavors meld, giving that classic Southern pudding texture.
Serve. Scoop into bowls or cut into squares if well chilled.
Add extra banana slices right before serving if you like.