Preheat oven to 350 degrees. Spray a 9 x 13 baking dish with non-stick cooking spray. (NOTE: I like to use the spray with flour in it.)
In a large mixing bowl place cake mix, root beer, eggs, and butter. Using an electric hand mixer, beat until smooth for 2 minutes.
Pour cake batter into prepared baking dish. Bake in preheated oven for 25-30 minutes until cake has pulled away from edges and a toothpick inserted into center of cake comes out clean.
Cool cake completely in baking dish.
In a separate large bowl place both envelopes of Dream Whip, 1 cup root beer, and vanilla extract. Whip together using electric hand mixer until soft peaks form and it holds it shape. (NOTE: it should have a cool whip consistency.)
Spread Topping onto cooled caked evenly. Dollop canned whipped topping on top of 15 pieces of cake. Then place a cherry on top of the dollops of whipped topping.
Cut cake in between the dolloped whipped topping to mimic a root beer float.