Pretty Please with a Cherry on Top is a short featured on the episodes Top, Bottom, Jump and Push, Over, Top. The medium of this short is a hand-painted "charcoal" style. It was directed by Courage the Cowardly Dog creator John R. Dilworth at his studio, Stretch Films, with animation by David Wachtenheim.
Bob asks his friends what should they put on top of their ice cream sundae. Lacey pours chocolate syrup on top, then Bob puts whipped cream on top, with everyone exclaiming how delicious it is. Then Mary Jane dumps three bananas on top, followed by Little Cup adding some sprinkles, and then the two girl shoes add nuts and butterscotch. Finally, Bob adds a cherry on top to complete the sundae. While everyone admires the large sundae, Bob adds that they need some spoons, and they all leave to get them.
When they leave, Plush walks on and notices the ice cream sundae, so he hops onto the table and devours it all. The gang comes back disappointed, and Bob suggests they "take it from the top". They recreate the large sundae again, this time even faster than before.