Make the Pineapple Cherry Layer

1. Drain the pineapple juice from the pineapple tidbits and slices. Reserve about a 1/2 cup of the juice for later. Set pineapple and juice aside.
2. Begin the caramelization process by adding the butter to a medium saucepan on medium high heat and melt.
3. Cook on medium-high, bringing to a simmer, for about 5-10 minutes or until pineapple softens and takes on a golden caramelized color.
4. Remove from heat and set aside to cool for about 15-20 minutes.

Make the Brown Sugar Cheesecake Layer

1. To make the cheesecake, add cream cheese, brown sugar and 4 tbsp pineapple juice to a mixer bowl and beat until smooth.
2. Stir in 4 oz of Cool Whip. Set aside.

Assemble the Trifles

1. Make a quick pineapple sauce by draining the juice from the cooked pineapple and add it to a separate bowl. Add 2-3 tbsp of reserved pineapple juice and stir together. Set aside.
2. Place eight 8 oz cups or jars in front of you and add a layer of cheesecake to the bottom of each container.
3. Top cheesecake layer with granola, then sprinkle a little bit of the pineapple sauce over the granola to give it a little more flavor and help soften it.
4. Top granola with a layer of pineapple and cherries.
5. Add another set of layers to each container; start with cheesecake and proceed to granola, pineapple sauce and caramelized fruit.
6. Cut both pineapple rings into quarters. You should have 8 pieces to top the trifles with.
7. Top trifles with some Cool Whip, a cherry and a quartered pineapple slice, if desired. Refrigerate until ready to serve. Trifles best for 2-3 days.