Using a paring knife, cut the top middle section of your cupcakes and fill each one with chocolate syrup. Cover the holes with the cupcake pieces you cut out.
In a stand mixer, slowly start beating butter, sugar, milk and vanilla to make your buttercream. Gradually increase the speed to high. The buttercream is ready once it forms stiff peaks.
Using a piping bag, generously frost your cupcakes with the buttercream.
Microwave your chocolate candy melts in 30-second intervals until completely melted. With a spoon, drizzle over on top of your frosted cupcakes. Top with sprinkles and a maraschino cherry.