First, make the homemade hot fudge: add the butter, evaporated milk, sugar, and cocoa powder to a small saucepan and heat over medium heat. As the butter and sugar melt, you'll be able to whisk everything together. Stir it every couple of minutes until it is a well-blended liquid.
Bring the mixture to a boil, still over medium heat, and boil for 5-7 minutes. Continuing to stir occasionally.
During the last 30 seconds of boiling time, stir in the chocolate chips with a spoon. Stir until they are completely melted and the hot fudge is liquidy. Immediately remove it from the heat and allow it to cool before making your sundaes.
While the hot fudge is cooling, make the waffle bowls. It is tricky, but you can do it. Start with two small bowls. Mine are 1-cup prep bowls. If you can't find a suitable bowl, a glass might work. The bowl or glass will need to go into the oven, so please use caution. Make sure the bowl or glass is safe to heat in the oven! Alternately, you could drape the waffle over the bottom of a muffin tin to bake it.
Microwave the waffle for 20 seconds. It will come out of the microwave soggy and pliable, just what you need. Drape the soggy waffle over the bottom of an inverted bowl. Use the second bowl to hold the waffle down and force it into the right shape.
Leave it alone. About a half hour later, my waffle had sufficiently dried out and held its shape when I removed the top bowl. If yours hasn't dried enough after a half hour, let it sit longer.
Preheat the oven to 250.
Turn the waffle bowl over into one of the bowls and bake it for 15-20 minutes, until it is crispy. If you can't find anything container that's oven-safe, try heating it on a cookie sheet. If you've let it dry long enough, it should hold its shape. Keep an eye on it if you go the cookie sheet route.
When the waffle bowl has become crispy, let it cool. You don't want it to melt your ice cream.
Once the waffle bowl has cooled off, put a scoop or two of ice cream in it. Top with whipped cream, a few spoonfuls of your homemade hot fudge, and a maraschino cherry.