Mastering the Whiskey Cocktail

The whiskey cocktail. Also known as the Old Fashioned is one of my favorites. The taste of the bourbon (or rye whiskey), the sweetness of the orange, the balance from the bitters and sugar. There’s something about that, that is undeniably delicious. I’ve had a lot of good Old Fashioned cocktails lately, some not so good, and it made me think. How did this cocktail originate? Where did it come from?

I recently read an article from that goes over the history, and I immediately got hooked.

Appears that this sweet nectar goes all the way back to 1880.  One article in the Kentucky region gives credit to the private club, called the Pendennis Club, making the very first one.  James E. Pepper was the man who took the earlier “gin cocktail” recipe created in 1862 and modified it to include whiskey.  He later brought the recipe to the Waldorf-Astoria hotel bar in New York City, bourbon was added, and the drink was born.

My Adventure For The Best

I live in Chicago and naturally as a guy in my late twenties wanted to check out the bars in my vicinity.  Since I’ve been on such a bourbon kick, I decided to see what my nearby brick and mortar establishments would offer.  I started at Commonwealth on Roscoe Ave. It’s a go-to spot for those that live around the Roscoe Village or West Lakeview area. They have a drink menu of six or so cocktails and lots of beer and different wines on the menu.  One of the items was an “Old, Old Fashioned”, so I was inclined to try it.

As I watched the bartender fill the glass with ice, pour Templeton Rye along with simple syrup, angostura and an orange and place my drink in front of me, I couldn’t help but feel somewhat dejected.  He rushed through making the drink, almost overflowing the glass with ice, just to get the drink to me as soon as possible.  I’ve had plenty of Templeton Rye Old Fashioned drinks before, but something was holding me back from truly enjoying this particular one.  I don’t know.  It just wasn’t the way that I would make an Old Fashioned.  Did I enjoy it? Definitely Yes.  Would I order another?  Most likely not.  The Templeton Rye he used was good, but not for those expecting a bourbon.

From there, I went on to Waterhouse Tavern right on Lincoln and Roscoe.  This bar for young adults has zero identity as being a whiskey bar.  I’ve been in here several times before, and it is a sports bar through and through.  I generally just drink the local IPA, Anti-Hero, and have an enjoyable time doing so.  This tavern doesn’t have necessarily a big selection of bourbons or whiskeys, however they always seem to have a special spirit on the board for around $7-8.  This time it was Buffalo Trace, arguably one of the better bourbon whiskeys out of a group.  From one of the bar stools I watched as John (one of the regular bartenders) pour a couple of ounces of Buffalo Trace into a mixing glass along with ice, a few shakes of bitters and simple syrup.  He took his time as he stirred, and made sure that the ice diluted the drink just right.  He took a few of the larger ice cubes and filled a small rocks glass as he strained the drink into the serving glass.  He carefully used a peeler to get a long curly strand of orange rind that he squeezed and shoved into the side of the glass.

As I took my first sip, it was just a delight.  This sports bar, known for it’s kinky trivia on Wednesday nights, and the lack of shoulder room on Friday and Saturday nights, actually delivered on a respectable bourbon cocktail.  It didn’t hurt that the bartender, mostly worn out from pouring drafts all night, filled with excitement when I ordered the bourbon.  This was the best one I have had so far.  I asked John what his secret was, and he told me that it’s quite simple – take your time and use the right amount of ice.

Here’s the recipe below:
– 2 ounces of fine bourbon or whiskey (in this case I used Bulleit)
– 1/4 ounce simple syrup
– 2-3 dashes of Angostura bitters
– Luxardo maraschino cherry to garnish the glass (use the leftover syrup on the spoon to use to stir the drink)
– Orange twist

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