The cookbook this is from is not vintage - but - I'd seen those pudding cups in a vintage cookbook, but the picture was tiny and black and white. So then I spotted it again in my 2001 "Frightfully Fun Halloween Crafts and Cooking". In fact, most modern cookbooks can be matched to a modern one - at least one in my library.
That ice thing was made by a rubber glove, which I think is pretty cool.
But notice the oranges with pudding in them. Both the vintage and modern cookbooks have elaborate ways to do this with piping and multiple ingredients. Really. It's going to be hard enough to cut out those faces.
Amy's version: After carving those faces with what must be an Exacto knife, make Jello Instant Chocolate pudding and spoon it in. Chill. Eat the orange insides while waiting. Then use cake decorator frosting tubes, not gel, and add the green and black if desired. Done.