Pour whipping cream, powdered sugar,2 TBS cherry juice, and vanilla in large mixing bowl. Beat with electric mixer on high speed until stiff peaks form.
Crumble half of one cupcake into the bottom of a jelly jar or parfait cup. Top with three cherries. Spoon a dollup of whipped cream over cherries, repeat until you reach the top of the dish. Garnish with additional whipped cream, sprinkles, and a cherry.