Southern Banana Pudding with Chessman Cookies Recipe

Our Southern banana pudding with Chessman cookies is a classic soul food dessert made with sweetened condensed milk and instant pudding mix. It’s creamy, fluffy, and ready in minutes—perfect when you want a quick, no-bake treat for holidays or everyday gatherings.

We’re excited to share our easy banana pudding recipe—rich, extra creamy, and light in texture. If you’ve enjoyed banana pudding from well-known bakeries, you’ll find this version equally delightful. It layers silky vanilla pudding with fresh banana slices and two cookie textures for a comforting Southern finish.

This old-fashioned dessert is versatile and forgiving. Our recipe pairs instant French vanilla pudding with Chessmen butter cookies and crushed vanilla wafers to create a dessert that’s both nostalgic and simple to make.

Ingredients

A full ingredient list with exact amounts appears in the recipe card below.

• Instant French vanilla pudding mix: We use Jell-O French Vanilla, but regular instant vanilla or banana-flavored pudding also work.
• Whole milk: Use cold milk to make the instant pudding set properly.
• Sweetened condensed milk: Adds richness and sweetness—Eagle Brand or another quality brand is recommended.
• Whipped topping (Cool Whip): Thaw according to package directions; you can substitute another whipped topping if preferred.
• Fresh bananas: Slice ripe bananas into rounds for layering.
• Pepperidge Farm Chessmen cookies: These buttery cookies add crunch and flavor—our favorite finishing touch.
• Crushed Nilla Wafers (optional): A layer of finely crushed wafers adds texture between pudding layers. Crush in a zip-top bag with a rolling pin or pulse in a food processor.

Step 1. Pour the cold milk into a large mixing bowl.

Step 2. Whisk in the instant pudding mix until smooth, about 2–5 minutes.

Step 3. Add the sweetened condensed milk and whisk until fully combined.

Step 4. Gently fold in the whipped topping until the mixture is light and creamy.

Step 5. Chill the pudding mixture in the refrigerator for about 5 minutes so it firms slightly.

Step 6. In a serving dish, arrange a layer of banana slices as the base for your first layer.

Step 7. Spread a layer of pudding over the bananas, then sprinkle with crushed vanilla wafer crumbs if using.

Step 8. Add a layer of Chessmen cookies on top of the pudding. Repeat layers until all ingredients are used, finishing with Chessmen cookies facing up for a pretty presentation.

• 1 (3.4-ounce) box French vanilla instant pudding mix
• 2 cups whole milk cold
• 1 (14-ounce) can sweetened condensed milk
• 1 (8-ounce) Cool Whip thawed
• 3-4 ripe bananas sliced (toss with 1 tsp lemon juice to prevent browning, optional)
• 2 (7.25-ounce) packs Pepperidge Farm Chessmen Butter Cookies
• 1 (11-ounce) box Nilla Wafers crushed to crumbs (optional)

• In a large bowl, whisk the pudding mix and cold milk until smooth, about 2–5 minutes.
• Stir in the sweetened condensed milk until combined.
• Gently fold in the whipped topping until the mixture is light and creamy.
• Chill the pudding mixture for 5 minutes to thicken slightly.
• Assemble in a serving dish: layer banana slices, pudding, crushed vanilla wafers (if using), and Chessmen cookies. Repeat layers and finish with a top layer of Chessmen cookies.
• Refrigerate for at least 4 hours or overnight before serving to allow flavors to meld and cookies to soften.

• Prevent browning: Lightly sprinkle bananas with lemon juice before layering.
• Keep ingredients chilled: Cold milk and whipped topping help the pudding set properly.
• Pick ripe but not overripe bananas: Too-ripe bananas can become mushy in the layers.
• Chill well: Refrigerate assembled pudding for at least 4 hours or overnight for the best texture and flavor.
• Garnish before serving: Add crushed cookies, extra whipped topping, or a drizzle of caramel to finish.