Beat cream cheese on medium until fluffy, add in powdered sugar. Combine vanilla pudding and milk, mix well. Add to cream cheese mixture and stir. Gently fold in 2 cups of whipped topping.
Slice bananas and toss with a little bit of the pineapple juice (or lemon juice) to keep them from browning. Drain pineapple, squeezing to remove all of the juice.
Line the bottom of a 9×13 pan with graham crackers. Top with half of the cream cheese mixture and the bananas. Add a second layer of graham crackers. Top with remaining cream cheese mixture and pineapple. Add a third and final layer of graham crackers. Top with remaining 2 cups of whipped topping, cherries and nuts. Drizzle with chocolate.