You can use sugar if you must, but most recipes call for making a simple syrup so you don't end up with undissolved sugar in your cup. Don't get me wrong, you are welcome to stand over the stove and make a simple syrup if you like, it truly is easy and if you are infusing it with something awesome it is totally worth it. But on most days I reach for one of two things... maple syrup or a good quality jam. I know it might sound a little strange, but jam totally works in a cocktail and makes it to where you can whip up a cocktail even without fresh fruit on hand! Today we are going to stick with maple syrup. It pairs perfectly with the bourbon and keeps this so simple. Let's jump in.
First off, the issue I know you have been up all night thinking about...crushed ice. I tried a bunch of different ideas on how to get the best crushed ice and the conclusion I came to is this: buy or make normal ice, wrap it up in a kitchen towel, bang it with your heaviest pot possible until it is crushed into billions of tiny pieces. Avoid hitting your hand in this process by using a large square tea towel instead of a small kitchen towel. This is the voice of experience talking here.
Now that we have ice. Let's make cocktails.