Rolo Stuffed Skillet Brownie

May 2025. Spring in Memphis, and I am 66, watching the azaleas and dogwoods bloom along my neighborhood walk, the annual resurrection that makes the winter worth surviving. The smoker wakes up in spring the way the whole city wakes up — slowly, with a stretch, then fully, with purpose.

Rosetta beside me through the week, steady as ever, the woman who runs this household with the precision of a hospital ward and the heart of a mother who has loved fiercely for 41 years of marriage. The BBQ class at the community center continues — students of all ages learning fire and smoke, and me learning that teaching is its own kind of cooking: you prepare, you present, you hope something sticks.

I made cornbread in the cast iron skillet — buttermilk, cornmeal, bacon drippings, the recipe that goes back to Mama and before Mama to her mama and before that to wherever the tradition began. Baked at 425 until golden and crusty, the edges dark and lacy, the center soft and crumbling. Some weeks cornbread is enough. Some weeks the simplest food is the most profound.

The week ended on the porch with Rosetta, the evening settling over Orange Mound, the smoker cooling in the backyard. The fire was banked but not out — it's never out, just resting between cooks, holding the heat the way I hold the tradition: carefully, permanently, with the understanding that what Uncle Clyde gave me is not mine to keep but mine to pass, and the passing is the purpose.

The cast iron skillet had already done its work that week — the cornbread golden and lacy at the edges, the center soft the way Mama always made it — but on Sunday evening with Rosetta on the porch and the smoker cooling down, I wanted something sweet to close it all out. That skillet wasn’t done yet. A Rolo Stuffed Skillet Brownie felt exactly right: rich, warm, a little indulgent, the kind of thing you share with the person who has held the household together for 41 years and deserves something good at the end of a steady week.

Prep Time: 15 min | Cook Time: 30 min | Total Time: 45 min | Servings: 8

Ingredients

1/2 cup (1 stick) unsalted butter, melted
1 cup granulated sugar
2 large eggs
1 teaspoon pure vanilla extract
1/3 cup unsweetened cocoa powder
1/2 cup all-purpose flour
1/4 teaspoon salt
1/4 teaspoon baking powder
16 Rolo candies, unwrapped (plus 6–8 extra for topping)
1/2 cup semi-sweet chocolate chips
Flaky sea salt for finishing (optional)

Instructions

Preheat and prepare. Preheat oven to 350°F. Grease a 10-inch cast iron skillet well with butter or cooking spray, making sure to coat the sides.
Mix the batter. In a large bowl, whisk the melted butter and sugar together until combined. Add the eggs one at a time, whisking after each. Stir in the vanilla extract.
Add the dry ingredients. Sift in the cocoa powder, flour, salt, and baking powder. Fold gently with a spatula until just combined — do not overmix.
Fold in chocolate chips. Stir the semi-sweet chocolate chips into the batter, then pour half the batter into the prepared skillet and spread it evenly across the bottom.
Add the Rolo layer. Press the 16 unwrapped Rolo candies in a single layer across the batter, spacing them evenly so every slice gets a gooey caramel center.
Top and finish. Spoon the remaining batter over the Rolos and smooth the top. Press the reserved 6–8 Rolos gently into the surface of the batter. Sprinkle with flaky sea salt if desired.
Bake. Bake at 350°F for 28–32 minutes, until the edges are set and a toothpick inserted near the center comes out with moist crumbs (not wet batter). The center will firm up as it cools.
Rest and serve. Let the skillet brownie rest for at least 10 minutes before slicing. Serve warm, straight from the cast iron, with a scoop of vanilla ice cream if you’re feeling generous.

Nutrition (per serving)

Rolo Stuffed Skillet Brownie — The Cast Iron Holds Everything Worth Keeping