I am not a fan of whiskey. I have had countless people tell me that I have not tried the right kind, or that I am not drinking it right, or I need to try it in a specific cocktail. I have tried all manners of ways to consume this infernal beverage, tried all varieties of brands from the very expensive to the probably-made-in-someone’s-bathtub, and I have never once found myself thinking, "My! What a tasty drink I have found!" I understand that a good whiskey requires a lot of skill and time, and with all that considered, good whiskey is wasted on me.

For this week’s article I wanted to branch out and try a mixed drink instead of food: something that was both traditional and fun. Immediately I thought of Don Draper from Madmen and how classy he looked drinking an Old Fashioned. I wanted that —the classy element. I wanted to go to a bar at the end of a long day and say to the barkeep, “Old Fashioned please. Neat.” The bartender and I would exchange a knowing look, and they would whip up some magical concoction that resembled everything glamorous about the mid-twentieth century. I was not put off by the fact that the drink was made with whiskey. In fact, I looked at this as an opportunity to acquire the taste for it. And because one is just not enough, I decided to choose four different places to try this drink (on different nights, of course).

The name Old Fashioned implies that it has been around for quite some time. Indeed it has been around since the late 1800s, getting its start in Louisville, Kentucky. The drink is a cocktail consisting of sugar that is crushed with bitters and fruit, often cherries and oranges, to release their flavors. It is accompanied by whiskey or sometimes brandy, and is normally finished with an orange on the glass. It sounded like something I might enjoy, and I figured that the whiskey would be present but not a dominant feature in this beverage.

The first place that I went to was Seven Saints. I always enjoy the food there and I heard from a good number of people that their mixed drinks were pretty great. The server I had was extremely helpful and answered any of the questions that I had. It was about to be my first Old Fashioned ever and I wanted to make sure I was doing it right. He recommended a rye whiskey because it made the drink dryer and the rye gives the beverage a good texture. The cost of the drink varies depending on what kind of whiskey used (Seven Saints has over 250 whiskeys in house) and the one my server picked for me made the drink come out to $11.50.  I decided to not order it neat because I know that I could never handle that.

The drink came out, and it looked rather plain. It did not have the orange on the side of the glass; the only fruit was on the bottom of the glass. When I drank it, the first thing that hit me was the whiskey. Initially the flavor was too much, but I tried it again and something magical happened. I overlooked the burn that comes with drinking hard alcohol and the flavors started to come out. I noticed that the drink hit me in the front of the mouth where all the sweet taste buds are. I noticed cinnamon as well, mixed with a sort of pleasant yet medicinal flavor which I later discovered was the bitters. I definitely understood why my server said that the whiskey gave it texture. Different flavors were hitting me at different times, starting with the sweet and ending with the bitters. The drink was overall very balanced. The whiskey’s dryness paired very well with the sweeter elements of the beverage, leaving a very smooth finish.

The next place I went to was Barrelhouse 34. I really love that place, and the atmosphere is exactly what I like in a bar: cheerful, but never hectic. I actually did go there after a very long day — and it hit the spot and was only seven dollars. This Old Fashioned was made with Bulleit Bourbon, which is known to be dry and has a high rye content. It was very similar to the one I had at Seven Saints. There was a healthy bit of cinnamon, and the fruit was a bit more prevalent, making the drink very sweet, but the rye helped balance that out. I normally do not care for fruity beverages, but this one was done well.

The next place I went to was V. Picasso. I had not been to this restaurant, but I walk by it so often and it is so well put together that I was looking forward to it immensely. The server there gave me the option between a standard Old Fashioned or the House Old Fashioned, made with apple brandy and Journeyman rye whiskey ($8). The second one sounded so appealing I had to get it. When I received it I noticed that it was very much how I imagined an Old Fashioned would look. It had the orange slice on the outside of the glass and the fruit was more crushed than the previous drinks so more of those flavors were released. The drink itself tasted like apple pie, and it was the first time that I was not hit with the flavor of the whiskey first. It tasted like it was flavored with mulling spice, and the orange came through more clearly as well. It was extremely good and exceeded my expectations.

The last place I visited was Quality. This bar is my normal go-to. I always feel at home there and the drinks are always on point. At this time, I was feeling pretty tired and a bit over the Old Fashioned, but I ordered it regardless. Unfortunately because of how tired I felt I forgot to take a picture (for shame!) but I assure you that it was a pretty drink and it looked much like all the other ones. I got it with Jim Beam this time because I had not tried it with an average whiskey. The very first thing I tasted was the whiskey, which was a little overbearing. Rather than giving up on the drink, I continue with the hopes of tasting more flavors. As I drank it, I noticed that the spice, which was one of the more dominant features in all the others, was more mellow, and that there was a really pleasant honey flavor that lingered on the palate that none of the other drinks possessed. Overall there was a bit too much whiskey for my taste, but it was pleasant all the same.

After all of that it is safe to say that I have not seen the light: I still do not like whiskey. I gave it the good ol' college try, but I'm not sure the Old Fashioned is my new go-to drink. Despite this, I still found elements of the drink to enjoy, and I must say that if I had to choose which one was my favorite I would have to pick V. Picasso. The restaurant's drink was the most balanced and had the best flavors. They were beautifully delicate and I could enjoy the drink without trying to ignore the whiskey. Don Draper made looking classy while drinking an Old Fashioned seem easy, but I have a feeling I did not accomplish the look with the same grace that he did. In the end I think I can be content with the fact that at least I tried.

All photos by Merry Thomas.