To prepare cookies, combine sugar and flour, stirring with a whisk. Add vanilla and egg, and beat with a mixer at medium speed 2 minutes. Cover and refrigerate 2 hours.
Preheat oven to 350°.
Cover a large baking sheet with parchment paper. Draw 6 (3-inch) circles on paper. Turn paper over, and secure with masking tape. Spoon about 1 tablespoon batter into center of each drawn circle; spread batter to outside edge of each circle. Bake at 350° for 6 minutes or until edges begin to brown. Carefully remove cookies from paper, and cool completely on wire racks. Repeat procedure with the remaining batter, reusing the parchment paper.
To prepare the filling, combine the ice cream, banana, and 1/4 cup peanuts, stirring well.
Place 1 cookie on each of 6 plates. Carefully spread about 1/3 cup ice cream mixture over flat side of each cookie. Top with remaining cookies, flat sides down, pressing gently. Top each sandwich with 1 tablespoon whipped topping, 1 tablespoon chocolate syrup, 1 teaspoon peanuts, and 1 cherry. Serve immediately.
This recipe originally ran in Cooking Light July, 2003 and was updated for the November, 2012 25th anniversary issue.