Pare apples, halve and seed, thinly slice. Place slices in a bowl; add 1/3 cup sugar and Sherry. Cover; let stand 2 hours, turning occasionally. In buttered shallow baking dish, place layer of apples, sprinkle with some of the bread crumbs and remaining sugar; dot with butter. Repeat layers until dish is filled. Place dish in shallow pan of hot water. Bake at 350ºF for 1-1/2 hours. Remove and place dish on tray or platter. Pour over brandy which has been sweetened and warmed. Set aflame and serve. Top with whipped cream.
Pairing wine with dessert is easy. In my opinion, a good Madeira goes with any dessert-or at least every dessert I've tried it with. From Creme Brulee to bananas foster to chocolate cake, Madeira stands up to all. It's especially good with this if you get a decent 5-year or 10-year from a producer like Broadbent. For $10 or so, you'll get a quality wine with caramel and nutmeg notes, which lend themselves nicely to the apple flavor. Cheers!