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Shaking versus stirring. There are two ways to make your cocktail; one is to stir it on ice in a mixing glass and the other one to brutalize that ice inside of a metal tin.
Generally speaking liquor on liquor drinks are stirred, and anything that involves a lot of citrus or needs to be light and airy will be put in a shaker. Shaking is going to incorporate air into the drink whereas stirring it sort of lets everything blend together and get nice and well melded.
So depending on what you want you're going to shake or stir your drink. An old fashioned for instance is always going to be stirred. If you see someone shaking a Manhattan you have my permission to throw things at them; they need to be stopped.
I did that once. I was at a bartending audition for a job. God help me; the manager shook a Manhattan. I thought the GM was going to pop a blood vessel. It was beautiful. You know, a liquor drink like an old fashioned or [Sassenach] can go in the mixing glass. When it pours out it's going to be silky and even on the tongue.
We're going to start by stirring a cocktail, and we're going to make a rye old fashioned. A rye old fashioned is simple; sugar, spirits, waters, and bitters. We're going to put in about two ounces. I'm a professional; I know exactly how long it takes to pour two ounces out of that. I suggest you use a jigger, or honestly, it's not a big deal. A bar spoon or roughly an eighth of an ounce of sweetener; this is [demoraris] syrup. It's made from dark sugar that still has molasses in it, so it's more rich, flavorful sugar as opposed to simply syrup which is made from white granulated sugar.
Bitters; in this case we have [angostura], which is a classic cocktail bitter, and two dashes should do us. You can feel free to substitute any bitters or sweeteners or spirit you like for that matter. The rye old fashioned is your classic, you know, this is how your grandfather drank, if your grandfather was a railroad baron. Mine was not.
You add ice, which you can crack or not crack depending. It'll speed dilution if you do, but it doesn't hurt if you don't. And you stir it; some people say it's 50 stirs, some people say it's 50 seconds. I just do it until it looks right, smells right, and you know, taste everything. Taste, taste; that's what you're doing this for after all--and that'll do us.
Take a nice good old fashioned julep strainer. We of course use pre-chilled glasses, because, why wouldn't we? You can stick them in the freezer and they'll chill up pretty quickly. Glass is a very bad thermal conductor, but once it gets good and cold it'll stay that way.
Strain it off into the drink. You'll notice we have avoided the brandied cherries, the orange wedge; those are options for you old fashioned. But they reflect a later period in the old fashioned's development, one where prohibition had reduced the quality of the spirits to being basically bathtub spirits, and you wanted as much sweet floral flavor as you could get to cover that fact that you were basically drinking wood alcohol and you were going to go blind. You're still going to go blind on this if you work at it hard enough, but it's a lot tastier, trust me.
Cut an orange twist carefully, very carefully. Express the twist by taking it in your fingers like so, and bending it in half gently. You can't see it in the light, but there's a little shower of essential oil that goes on top and it gets shinier on top. Wipe it in and enjoy.