In a mixing bowl, beat the cream cheese until it’s smooth and creamy. This should take about 2-3 minutes with a hand mixer.
Gently fold in the whipped topping or the whipped heavy cream until well combined.
Drain the pineapple chunks if they are in syrup.
In your trifle cups or small glasses, add a layer of crushed vanilla wafers, followed by a layer of the cream cheese mixture, then a layer of pineapple chunks. Repeat until you reach the top.
Finish each trifle with a dollop of whipped topping and a sprinkle of crushed vanilla wafers.
Refrigerate the trifles for at least 1 hour before serving.