Beat the softened cream cheese with granulated sugar until completely smooth and no lumps remain. In a separate bowl, whip the heavy cream with powdered sugar and vanilla until stiff peaks form. The cream should hold its shape when you lift the beaters. Gently fold the whipped cream into the cream cheese mixture until just combined.

Line the bottom of a 9x13-inch dish with whole graham crackers, breaking pieces as needed to fit snugly. This foundation layer will absorb moisture and transform into tender cake. Spread half of the cream mixture evenly over the crackers, reaching all corners.

Spoon half of the cherry pie filling over the cream layer, distributing the cherries evenly. The sweet cherry juice will seep down and flavor the entire dessert. Add another layer of graham crackers, pressing gently to help them adhere to the filling below.

Spread the remaining cream mixture over the second cracker layer, then top with the remaining cherry filling. Create a beautiful presentation by arranging the cherries in an attractive pattern. Cover tightly with plastic wrap, ensuring it doesn't touch the surface.

Refrigerate for at least 4 hours, though overnight produces the best texture. The graham crackers will soften completely, creating distinct cake-like layers that slice beautifully. You'll know it's ready when a knife cuts through cleanly without cracking the crackers.