This Chessmen Banana Pudding isn’t just a dessert, it’s a memory in the making. It’s unapologetically rich, creamy in all the right ways, and topped with those golden shortbread beauties you’ll wanna fight your cousin over. If you’re craving homemade banana pudding with cream cheese that feels like a hug from Nana herself, you’re in the right kitchen.
Why You’ll Love This
- Buttery Chessmen cookies make every bite a melt-in-your-mouth moment.
- No baking required just chill and serve.
- The cream cheese filling adds a rich, velvety twist to a classic Southern treat.
Gather Your Goodies
This Chessmen Banana Pudding gets its charm from layers of texture and flavor. Let’s talk about what goes into each one and why it matters.
- 2 bags Pepperidge Farm Chessmen Cookies: These are your buttery base and crown jewel topping—skip the wafers this time, y’all.
- 6 ripe bananas: Sweet, tender slices add that unmistakable banana pudding soul.
- 1 (8 oz) package cream cheese (softened): This is where that silky magic happens homemade banana pudding with cream cheese is a whole different level.
- 1 (14 oz) can sweetened condensed milk: It makes everything dreamy-sweet and smooth as Sunday gospel.
- 1 (5 oz) box instant vanilla pudding mix: Adds thickness and a light vanilla kiss don’t skip it.
- 2 cups cold milk: Helps that pudding set up just right, not too stiff, not too runny.
- 1 (12 oz) container frozen whipped topping (thawed): Folded into the cream layer, it keeps things light and luscious.
Let’s Make It Together
If you’ve ever layered a trifle, you’re halfway there. Here’s how we make this nostalgic Southern dessert the easy and light banana pudding way—but with maximum flavor punch.
1. Line the bottom of a 9×13 dish with one full bag of Chessmen cookies. This becomes your sweet, buttery crust. Let ‘em overlap a bit. It’s okay to get messy.
2. Slice your bananas about ¼-inch thick and layer them generously over the cookies. This ain’t the time to skimp this is banana pudding, after all!
3. In a large bowl, beat the softened cream cheese with the condensed milk until smooth. This is your base layer of love smooth, rich, and slightly tangy.
4. In another bowl, whisk together the pudding mix and cold milk. Let it sit a few minutes till it thickens slightly, then fold it into the cream cheese mixture.
5. Gently fold in the whipped topping. Don’t stir too hard you want that fluff!
6. Pour the pudding mixture over your banana layer. Spread it evenly with a spatula like you’re tucking it in for a nap.
7. Top with the second bag of Chessmen cookies. Press them down ever so slightly. Cover and refrigerate for at least 4 hours or overnight if you’re patient (I’m not).
A Few Mistakes You Can Avoid
Chessmen Banana Pudding isn’t fussy, but she’s got her moods. Here are a few things to keep in mind:
- Don’t use underripe bananas. You want that full banana flavor, not a starchy bite.
- Don’t skip softening the cream cheese. Cold cream cheese will clump and ruin that silky filling.
- Don’t rush the chill time. This dessert needs a few hours in the fridge to firm up and allow the cookies to soften ever-so-gently.
Pro Tips
Listen, I’ve made this pudding more times than I’ve seen sweet tea spilled on a porch swing. Here’s what makes it truly shine:
Let your bananas rest before slicing. If they’ve got a few brown specks, they’re perfect. Too green and the flavor’s flat; too brown and things get mushy.
Fold with love. Folding in the whipped topping gently is what keeps your pudding fluffy. Treat it like you’re folding in whipped cream to a meringue gentle, swooping motions.
Use a glass dish if you’ve got one. Not only does it look pretty with those layers, but it also helps you gauge just how thick your pudding is setting up.
Oh, and bonus: if you’re entertaining, serve it in mini dessert cups! Talk about personal banana pudding magic with zero mess.
Your Little Bonus Tip
Want to switch things up without messing with tradition? Here’s an idea that’s perfect for summer get-togethers or date-night desserts:
Make it a frozen banana pudding pie! Crush half the Chessmen cookies and mix with melted butter. Press into a pie dish. Freeze for 10 minutes, then fill with the pudding mixture and banana slices. Top with the rest of the cookies and freeze for 3–4 hours. Slice, serve, and savor a Southern dessert with a cool twist.
How to Serve It Just Right
This dish is best cold from the fridge, preferably with good friends around and sweet tea in hand. Try it alongside other easy desserts using bananas or as part of a casual Sunday dinner spread with Mini Tiramisu Cups and Cream Berry Fairy Cups.
For single servings, layer it in mason jars and tie twine around the rim. It’s an adorable way to serve personal banana pudding at parties without the scooping stress.
Chessmen Banana Pudding
Equipment
- 9×13 inch dish
- Mixing Bowls
- electric mixer
Ingredients
Main Ingredients
- 2 bags Pepperidge Farm Chessmen Cookies
- 6 ripe bananas sliced
- 8 oz cream cheese softened
- 14 oz sweetened condensed milk
- 5 oz instant vanilla pudding mix
- 2 cups cold milk
- 12 oz frozen whipped topping thawed
Instructions
- Line the bottom of a 9×13 inch dish with one bag of Chessmen cookies.
- Layer the banana slices evenly over the cookies.
- In a bowl, beat softened cream cheese with sweetened condensed milk until smooth.
- In another bowl, whisk together pudding mix and cold milk until slightly thickened.
- Fold the pudding into the cream cheese mixture until combined.
- Gently fold in the whipped topping using light, sweeping motions.
- Spread the pudding mixture evenly over the bananas.
- Top with the second bag of Chessmen cookies, pressing them down slightly.
- Cover and refrigerate for at least 4 hours or overnight before serving.
Notes
- Use extra-ripe bananas for more flavor.
- Chill overnight for best results.
- You can make a frozen pie version by crushing cookies with butter and freezing the base.
FAQs
How long does Chessmen banana pudding last in the fridge?
It’ll keep beautifully for about 3 to 4 days, though the cookies soften over time. Still delicious, just a little less crisp. I like it best after a full overnight chill everything melds together into magic.
Can I make it lighter or healthier?
You sure can. Use light cream cheese, fat-free sweetened condensed milk, and sugar-free pudding mix for a light banana pudding version. Swap in sliced strawberries or blueberries for half the bananas if you like a little tartness to cut the richness.
Is there a difference between Chessmen Banana Pudding and Chess Banana Pudding?
Great question some folks say Chess Banana Pudding to shorten the name, but they usually mean the same thing: that classic banana pudding made fancy with Pepperidge Farm Chessmen cookies instead of vanilla wafers. No wrong turns here, friend.
Savor the Last Bite With Me
This recipe isn’t just sweet it’s soaked in memories. It’s for when you’re missing home, celebrating with friends, or just need something real good and real easy. Whether you call it Chessmen Banana Pudding, black banana pudding with depth from extra-ripe bananas, or dress it up for dessert cups, you’re making something that’s more than a recipe. It’s a little Southern love on a plate.
And if you’re as into stories behind your sweets as I am, this piece from Serious Eats dives into how banana pudding became a Southern icon. Spoiler: we’ve been loving it longer than we’ve had refrigerators.
