Usually I keep my liquor tastes simple. Straight bourbon or scotch, a nice craft beer, or a classic glass of Italian red wine, at least three years old. However, on occasion I do enjoy a nice cocktail with my cigar. So, yet again the team and I decided to do some investigative research to find some great cocktail and cigar pairings. While my two compatriots picked one drink each, I chose my top three because I like options. Let us know what you think!

Black Russian & Montecristo White Series Magnum Especial

For those interested in the history of beverages, I have a little fact for you. The Black Russian was not created in Russia In fact its origins lie in Belgium where a local bartender crafted it for a dear friend of his. The standard makeup of the drink includes two parts coffee liqueur such as Kahlua (Black) and then 5 parts vodka (Russian) served over ice in an old fashioned glass (we will discuss this beverage later). It is a great mix of rich coffee notes and the intense burst of flavor from the vodka. For fans of “the Dude”, the addition of cream turns this into what is known as a white Russian. For the Black Russian, however, we found a Montecristo White in the magnum size was quite the partner. Its creamy and light coffee notes as well as its smooth aroma was the perfect match for the rich cordial.   

Cuba Libre & ACID Blue Blondie

This familiar cocktail has a rich history as well. First off, you have definitely had a Cuba Libre, you just didn’t know it. In the US, we just call it a Rum and Coke. Its origins trace back to the Spanish-American War. According to Bacardi, while US troops were drinking at a bar in Havana, a Captain entered and ordered Bacardi and Coca-Cola with a slice of lime, sparking interest among his troops. While the Cuba Libre, “Free Cuba”, may have a different connotation today, the drink still serves as a favorite for bars and lounges throughout the American continents. Due to the sweetness and fizzy texture of the drink, we went with the Acid Blue Blondie. Its sweet and herbal aroma with its mellow body paired quite well with the drink. Also, this is a drink that is easy to get down, as is the Blondie, so smoking and drink time are comparable.   

Sazerac & San Cristobal Revelation Legend

I doubt anyone under the age of 35 has even heard of this drink unless you’re from south of the Mason Dixon Line. Sazerac is a heavy southern cocktail with its origins reaching to before the Civil War in the popular port city of New Orleans. Its official makeup is 5 parts cognac, 1 part absinthe, one sugar cube, and a few dashes of bitters. Although it takes its name from the original cognac used to make the drink, today you can substitute the cognac for rye or bourbon. It is so popular in the “Big Easy”, that in 2008 it was named the official cocktail of the city. The smooth spice of the cognac blends effortlessly with the bitters and the minty, anise flavor of the absinthe. It takes an immensely flavorful cigar to pair up with this southern beverage, so I went right in my humidor and took up a San Cristobal Revelation that has been sitting there about a year. Its spicy notes mixed well with the cognac portion, while a subtle cocoa zest from the Sumatra wrapper stood face to face with the absinthe flavor and didn’t blink. An unusual pairing maybe, but it works out well.  

Old Fashioned & Alec Bradley Prensado Robusto

This drink is so iconic, it has a glass named after it. If you believe the stories, it was actually the Old Fashioned that created the name “cocktail”. This drink dates all the way back to 1806, when there were still Revolutionary War soldiers walking around! It has stood the test of time and remains a favorite among higher end lounges and bars. It consists of 4.5 parts Bourbon or Rye, 2 dashes of bitters, 1 sugar cube, and a little plain water. Most of the time it is served with either an orange twist or a cherry. Depending on the whiskey you choose, it will most likely have a spice with some wood notes as well as a dash of earth and zest from the bitters. To pair with this iconic drink, I needed an iconic smoke. So I went with 2011 Cigar of the Year, the Alec Bradley Prensado. As smooth as it is flavorful, each puff delivers notes of earth, wood and spice. It seems each sip was spot on with each puff. Next time you're in a cigar bar, light up a Prensado, order yourself an Old Fashioned and sit back and enjoy.    

Manhattan & Hoyo de Monterrey Dark Sumatra Media Noche

The Manhattan is a cocktail I have been ordering regularly for many years. It may seem too fancy for many, but you get the right bartender with the right whiskey and it is a life changer. This cordial has an odd history as well. It traces its origins to, as you guessed it, Manhattan in 1870. It was crafted during a banquet held by Jennie Jerome, although history buffs may know her as Lady Randolph Churchill, the Brooklyn born mother of Sir Winston Churchill. See how cocktails can broaden your horizons? Its official makeup consists of 5 parts Whiskey, 5 parks red vermouth and a dash of bitters. My go-to whiskey with this cocktail is always Maker's Mark. It is smooth and rich with a subtle sweetness to it that goes great with the vermouth. Many may see my cigar choice as unusual, but it worked out perfectly. I went with an aged Hoyo de Monterrey Dark Sumatra. This full-bodied smoke was sitting in my humidor for a while so it had smoothened out a bit. It is rich and bold with notes of chocolate, earth, leather and a subtle sweetness. It was the sweetness and earth that really made this a pairing for the ages.