In a medium bowl combine the Jell-O powder and 2 cups of boiling water. Mix until the Jell-O is dissolved (about 2-3 minutes).
Add the can of raspberry pie filling and topping to the Jell-O. Mix until the pie filling is dissolved (or no longer clumpy). Once dissolved, empty the can of crushed pineapple (including the juice) into the Jell-O mixture.
Add the pomegranate fruits to the Jell-O. Pour the Jell-O mixture into a 9x13" pan. Place in the refrigerator to set. About 3-4 hours.
Once Jell-O is set, remove from the fridge. Slice bananas (about 1/2" thick) and distribute evenly over top the Jell-O. Make the whipped topping:
In the bowl of a stand mixer fitted with the whisk attachment, or using a hand mixer, add the heavy whipping cream, powdered sugar, and vanilla. Beat until stiff peaks form.
Spread the whipped topping mixture over the sliced bananas. Serve immediately, or place back in the fridge to keep cold until ready to serve.