Make the topping: Place butter in skillet, place skillet in oven, and melt butter. As soon as butter is melted, remove and stir in brown sugar, carefully mixing well with a rubber spatula so as not to tear foil. Arrange pineapple slices over butter/sugar spread. Place cherries in center of pineapple and pecans between the slices.
Make the batter: In the bowl of an electric mixer, cream butter, adding sugar gradually, and then add eggs and beat well. Stir flour, baking powder, and salt together in a small bowl. Combine buttermilk, syrup, and vanilla in a small measuring cup. Add flour mixture alternately with buttermilk/syrup mixture, beating well after each addition. Spread batter evenly across mixture in skillet.
Bake for approximately 45-50 minutes, or until toothpick inserted in center of cake comes out clean. Place a large cake plate over pan, and invert to remove. Peel off aluminum foil, pressing back any pineapple that may be stuck to the foil.
We have adapted this recipe for a cast-iron skillet.
Recipe from The Unofficial Mad Men Cookbook: Inside the Kitchens, Bars, and Restaurants of Mad Men by Judy Gelman and Peter Zheutlin (Smart Pop, 2011).