Drain pineapple making sure to remove as much moisture as possible. Set aside. Drain pears and cut into small pieces. Set aside.
In a large mixing bowl, whisk together gelatin and boiling water until the gelatin mix dissolves.
Add cream cheese to the bowl, and use a hand mixer to blend the jello and cream cheese together until completely combined. Be careful! The jello is HOT. There will be lots of bubbles on top, that's okay.
Place mixing bowl in the fridge for 1 hour.
After jello has cooled, remove the bowl from the fridge. If the jello has started to set around the edges, use a whisk to mix everything up.
Add whipped topping to the jello and whisk until combined and smooth.
Fold the pineapple and pears into the jello mixture.
Pour the jello salad into a 2-quart casserole dish. Transfer to the fridge and chill for 3 hours, or until set.
Remove salad from the fridge and serve as is or top with dollops of whipped topping and cherries.
You can also use whipped cream to garnish your salad, but it will start to breakdown quickly due to the gelatin.