Prepare cookies: Preheat oven to 350°F. Line two large baking sheets with parchment paper and set aside.
In the bowl of a mixer, combine cake mix, eggs, oil, and water. Mix on medium low speed until combined. Using a small cookie scoop, scoop batter on lined baking sheet, several inches apart. Bake for about 7 minutes, until edges are set and centers spring back when lightly touched. Remove from oven and let cool on baking sheet for a few minutes. Remove to wire rack to finish cooling.
Prepare frosting: In the bowl of your mixer, beat butter, cream, and vanilla on medium low until combined. Slowly add powdered sugar until just barely mixed in. Increase mixer speed to high and beat for a minute and a half, until smooth and fluffy. Fold in sprinkles and fill a piping bag fitted with a large round tip (alternately, you can use a resealable sandwich bag with the corner snipped off).
Pipe frosting on COMPLETELY COOLED cookies, bottom side of cookies facing up. Place frosted cookies on a large baking sheet and refrigerate for one hour.
Prepare candy coating: In a microwave safe bowl, candy melts and vegetable oil in the microwave, stopping to stir thoroughly every 30 seconds. Repeat process until candy is melted and smooth. Dip cookie frosting in candy, holding upside down for a moment to allow excess to drip off. Sprinkle with sprinkles and top with a cherry. Allow candy to set before serving.