Lightly grease an 8x8 square baking dish with baking spray or butter.
Beat butter in bowl of stand mixer until lightened in color, or about 3 minutes.
Sprinkle 1/2 cup sifted powdered sugar over the butter and beat in until combines and fluffy, 3 minutes or so.
Beat flour in, 1/2 cup at a time, mixing in between.
Press crumbly dough firmly into 8x8 baking dish with fingers. Refrigerate at lest 1 hour.
Bake chill shortbread in preheated 325 degree oven for 28-35 minutes. Check at 25 minutes (in case oven runs hot), and remove when shortbread is light brown. Remove from oven and let cool completely.
Beat cream cheese in stand mixer until light and fluffy. Sprinkle in 1/4 cup powdered sugar and beat until smooth and creamy.
Spread cheesecake mixture over top of cooled shortbread layer.
Spoon dollops of cherry pie filling on top and use spoon or icing spatula to spread evenly.
Refrigerate until ready to serve, then cut into squares or rectangles to serve.