Preheat oven to 325°F. Lightly coat a 10-inch cast-iron skillet with cooking spray. Beat brown sugar, granulated sugar, and butter with a heavy-duty electric stand mixer at medium speed until light and fluffy. Add egg, bourbon, and vanilla, beating until blended.
Whisk together flour, baking soda, and salt in a bowl. Add to butter mixture gradually, beating at low speed until combined.
Add 1 cup halved thin crème de menthe chocolate mints; beat until combined.
Spread mixture evenly in prepared skillet. Top with remaining 1/4 cup halved thin crème de menthe chocolate mints.
Bake in preheated oven until golden and set, about 50 minutes. Let stand 15 minutes; cut into wedges. Serve with vanilla ice cream.
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