Preheat oven to 350 degrees F. Liberally grease a 13x9" baking pan with cooking spray. Unroll one of the crescent dough sheets and lay it flat in the bottom of the pan. Pinch together all the seams to seal. Set aside.
In a large bowl, beat together the cream cheese, one (1) cup of the brown sugar and the vanilla extract together until creamy and smooth, about 1 minute. Beat in the crushed pineapple, juice and all, until combined. Mixture may be slightly lumpy because of the pineapple; that's okay. Spread the cheesecake mixture evenly over the bottom crust.
Immediately unroll the remaining crescent roll sheet over the cheesecake layer, pinching the seams to seal. Pour the melted butter evenly over the top layer. In a small bowl, whisk together the remaining brown sugar and the ground cinnamon; sprinkle this liberally over the melted butter.
Bake for approx. 30-35 minutes or until golden brown and center is set. Cool completely, then refrigerate for at least 4 hours or until chilled. Cut into bars and garnish with whipped cream and cherries, if desired.