Prepare cake according to package directions. Stir in crushed pineapple. Pour batter into a lightly greased 9x13 pan. Bake according to package directions.
While cake is baking, stir together strawberry topping and sweetened condensed milk. Set aside.
Remove cake from oven. Poke holes all over cake with a handle of a wooden spoon. Pour strawberry mixture over cake. Cool completely.
Place sliced bananas on top of cake. Spread Cool Whip over bananas. Drizzle chocolate syrup over Cool Whip. Sprinkle chopped nuts on top of cake and place cherries on top. Refrigerate at least 2 hours before serving.