Preheat the oven to 350 degrees. Line a round pizza pan (14 inch diameter or smaller) with parchment paper allowing paper to overhang by a few inches on both of the pan (this allows lifting the pizza out of the pan). Spray the paper and any uncovered area of the pan with non-stick spray.
Prepare the sugar cookie mix as directed on the package. Roll the dough out and fit to the pan. Press to fully cover the pan using a mixing spoon and fingers. Bake in the preheated oven until lightly golden (8-10 minutes). Note: every mix and oven is different so watch while baking and do not over bake. I removed mine at 11 minutes and it was not a true golden color but was cooked. Set on a cooling rack until it has fully cooled.
While the cookie is cooling, prepare the topping. Add the softened cream cheese to a mixer bowl and beat at high speed until fully creamed. Add the whipped topping, vanilla extract, confectioner’s sugar and food coloring; beat on medium to incorporate, raising the speed to high to beat into a creamy frosting. Note: it may appear lumpy during the beating process but continue until it becomes creamy. Add food coloring to achieve desired orange color (I wanted a light sunset hue).
When the cookie if fully cooled, spread the frosting evenly to cover the entire cookie. If needed the cookie can be lifted from the pan by the parchment paper to do this step.
To create the face: Cut two eyes and a mouth from the fruit leather. I cut two tall triangles using the length of the fruit leather. Cutting the mouth horizontally aligned with the length of the fruit leather works best. Place the eyes and mouth where you want them.
Make vertical lines with the clementines imitation the ridges in a pumpkin. You can develop a pattern that appeals of simply place one row of clementine segments facing one direction with the next row facing the opposite direction and continue alternating in the fashion. I placed the orange segments randomly within the clementine rows.
Once the Jack-o-Lantern is assembled, cover with plastic wrap and refrigerate until serving. Cut into serving pieces with a sharp kitchen knife or pizza cutter.