***Crust*** 1 cup unsalted butter 2 tablespoons sugar 2 cups flour ***Vanilla Pudding Layer*** 3 egg yolks 1/2 cup sugar 1/4 cup flour 2 cups milk 2 teaspoons vanilla extract 2 tablespoons unsalted butter ***Cream Cheese Layer*** 1 package (8 ounce size) cream cheese, softened 1/2 cup sugar 1 teaspoon vanilla extract 1 teaspoon lemon juice 1 cup whipping cream ***Pineapple Caramel Layer*** 1 can (8 oz. size) crushed pineapple, drained well 1 jar (8-10 oz. size) caramel or chocolate sauce ***Whipped Cream Layer*** 1 1/2 cup whipping cream 3 tablespoons powdered sugar 1 tablespoon vanilla extract ***Chocolate Glaze*** 2 ounces semisweet chocolate, chopped 2 tablespoons unsalted butter 1/2 teaspoon vanilla extract
Butter a 9x13 inch pan. Set rack in center rack of oven and preheat to 350.
For Crust: Beat butter and sugar until fluffy. Add flour and using low speed on mixer blend until mixture is pebbly and can be pressed together. Press mixture on bottom and up the sides of buttered pan. Bake until golden, about 20 minutes. Cool completely.
For Pudding: Beat yolks lightly and set aside. Whisk sugar, flour and milk in a medium pan until free of lumps. Set over medium heat and cook stirring constantly with a wooden spoon just to boil.
Remove from heat and whisk a little of the hot, thick pudding into the beaten yolks, then pour the yolk mixture back into the main pudding mixture, whisking well. Continue cooking 1-2 minutes stirring constantly until thick.
Pour pudding back into a bowl and add vanilla and butter stirring until butter melts. If pudding has lumps pour through a fine strainer. Chill, with wax paper pressed directly on the surface of the pudding until ready to use.
For Cream Cheese: Beat cream cheese, sugar, vanilla and lemon juice just to blend. In a separate bowl whip cream to medium stiff peaks. Fold a scoop of whipped cream into beaten cheese, then fold in remaining cream into cheese.
To Assemble: Spread crust with cream cheese mixture. Top with pineapple, then drizzle with caramel or chocolate sauce. Spread pudding over pineapple-caramel.
For Whipped Cream: Whip the cream, powdered sugar and vanilla to stiff peaks. Spread over the top and chill well.
For Chocolate Glaze: Melt the chocolate and butter over low heat, stirring until smooth and completely melted. Remove from heat and stir in vanilla.
Drizzle over dessert in zigzags back and forth across the cake to decorate.
Didn't love the combo of chocolate and pineapple so I made this again with the caramel sauce in the pineapple layer and drizzled the top with additional caramel sauce instead of chocolate. That was much better in my opinion.