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Place 2 tablespoons each of chocolate syrup, sprinkles and peppermint topping on separate small plates. Working with one glass at a time, turn two 8 to 10-ounce glasses upside down and swirl the rim of the glasses through the chocolate syrup to coat the lip of each glass. Still holding the glasses upside down, dip the chocolate rim of each glass in the sprinkles and peppermint topping to coat, pressing lightly to adhere. Return glasses right-side up and place in the freezer until ready to use.
Combine ice cream, eggnog, coffee liqueur or bourbon, and remaining 2 tablespoons chocolate syrup in a blender and process until smooth, about 30 seconds. Remove prepared glasses from the freezer and drizzle the inside of each glass with additional chocolate syrup if desired. Divide prepared milkshake between glasses and top with whipped topping, popcorn, sprinkles and more chocolate if desired. Serve immediately.
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