1sleeveGraham Crackers, (crushed, 9 graham crackers)
6largeBananas
Instructions
Start by making the banana whipped cream. Add heavy cream to a medium saucepan over low heat. Bring to a low simmer, about 10 minutes, then add in sliced bananas. Remove from heat and allow it to sit at room temperature for an hour, then cover with plastic wrap and place into the refrigerator. For at least 4 hours, until cold throughout (ideally overnight for the best flavor).
While the whipped cream is resting, begin making the homemade vanilla pudding. Add whole milk to a medium saucepan over low heat, about 5 minutes until just warm (do not boil). In a separate mixing bowl, whisk together egg yolks, granulated sugar, salt, and cornstarch.
Begin adding the warm milk to the egg yolk mixture, slowly, constantly whisking so as to not cook the eggs. Once all of the milk is added, pour everything back into the saucepan and place back onto the stove over medium heat, stirring constantly until it begins to thicken, about 10-15 minutes. Once you’re able to see ribbons in the pudding, you’re nearly there, keep whisking until it reaches a thick, pudding-like consistency. Remove from the heat and add in the butter, vanilla bean paste (or vanilla extract), nutmeg, pinch of salt, and banana extract (optional) and whisk vigorously for 1 minute. Pour into a large bowl and cover with plastic wrap. Place into the refrigerator to set for at least 2-4 hours, once it’s cold throughout.
Once both the pudding and the banana cream mixture are cold, remove the banana cream bowl from the refrigerator. Using a fine mesh sieve, strain the cream into the bowl of a stand mixer, removing the bananas. Gently push the bananas to remove as much cream as possible (it’s ok to get a little bit of banana into the cream, this adds more flavor) Fit the mixer with the whisk attachment. Beat on medium speed for about 3 minutes, until soft peaks form.
In a separate bowl, use an electric hand mixer to mix together sweetened condensed milk and cream cheese until smooth. Then add to the stand mixer and continue to mix until stiff peaks form, about another 2-3 minutes, do not overmix.
Remove the pudding from the refrigerator - if it appears lumpy, just mix it together for a minute or two with the hand mixer to make it nice and smooth. Crush up a sleeve of graham crackers.
Crush up a sleeve of graham crackers.
Now assemble. In a 7 or 8 inch trifle dish (I used this trifle bowl). Add just enough whipped cream to the bottom of the bowl to coat. Add in a layer of chessman cookies, then sliced bananas, then cover with half of the pudding. Sprinkle a layer of graham cracker crumbs on top, and then repeat.
For the top layer, after adding the graham cracker crumbs, top with bananas, slightly crushed chessman cookies, and the remaining banana whipped cream. Allow it to chill in the refrigerator for at least 2 hours.
Before Serving, Sprinkle any remaining chessman cookies on top and garnish with sliced bananas.
Video
Notes
Serve cold always! This is not a warm pudding situation. Banana pudding needs to be served chilled for best results!
Use ripe bananas! When they're just spotted, they're perfect. At this stage, they'll hold their shape a little better and won't become soggy as quickly. I don't recommend using black bananas like you'd do for banana bread. They'll become slimy and are too sweet.
Temper your eggs carefully! When making the custard, slowly whisk hot milk into the yolks to prevent scrambled eggs. This step is crucial for a smooth, lump-free pudding.
Let the pudding cool before layering. The pudding needs time to set before layering along with the banana whipped cream. Both should be nice and cold before assembling the banana pudding.
Layer smart. Start with cream on the bottom, then the whipped cream and cookies. Put the cookies on top to prevent them from getting soggy too fast. Then alternate pudding, bananas, and cookies.