Arrange the rye cocktail bread in a single layer on a baking sheet. Brush with olive oil, then sprinkle with salt and freshly cracked pepper. Bake for about 10 minutes or until the bread starts to brown and become crisp. Set aside
In a large bowl, cream together the cream cheese, sauerkraut, thousand island dressing, pastrami, and Swiss cheese by hand or using a mixer. Add salt and pepper to taste.
Spoon the mixture into a 10-inch skillet (or any oven safe baking dish). Bake for 10 minutes. Remove from the oven and stir, then return the mixture to the oven for an additional 10 minutes or until bubbly. For a little browning on top of the dip, set your oven to broil. Watch carefully and remove when browned to your liking.