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Some cocktails are ridiculously simple to make. A Cuba Libre (rum and Coke) is so widespread in large part because of the ease of preparing it. While these simple cocktails have their place, the increased effort involved in making more complex cocktails is usually worth it. At the same time, there are also some drinks that may seem easy or simple, but are actually some of the hardest cocktails to make. It's not enough to follow a recipe with these cocktails: they can only be conquered through frequent practice.
The Old Fashioned got its name because at one point, the word "cocktail" referred simply to a spirit mixed with bitters and sugar to temper the harsh-flavored bootleg spirits during the prohibition era. Today, the whiskey-based Old Fashioned is one of the pinnacles of the modern craft cocktail scene and considered a staple of NYC nightlife. Because of its simplicity, however, the Old Fashioned is without a doubt one of the hardest cocktails to make. The trick is to take your time with it: start with high-quality sugar and bitters (Angostura is totally fine) and muddle them until the sugar is completely dissolved. Use a high-quality bourbon or rye, keep it light on the garnishes, and use the biggest ice cube you can get your hands on to reduce dilution.
The whiskey sour and the Old Fashioned are undoubtedly the two most iconic whiskey cocktails of all time. Whereas the Old Fashioned is hard to perfect because of its simplicity and subtlety, the whiskey sour has a completely different problem: sour mix. Sour mix began as a combination of citrus juice and sugar, which are common ingredients in a variety of cocktails. For ease of production and to save money, most of these mixes today are produced from citric acid and a variety of sweeteners and chemicals. As you'll see, sour mix is a root problem for many of the cocktails on this list. In the case of the whiskey sour, there are a number of recipes that can give you delicious results. Beyond a shadow of a doubt, however, I can tell you that none of those recipes call for sour mix.
The refreshing combination of white rum, mint leaves, lime juice, and sugar in a mojito make it one of the go-to drinks for a hot summer day. While it is no doubt delicious, it is one of the most notoriously time-consuming drinks to make. Bartenders tend to resent anyone who orders them, as the drink requires the bartender to spend time muddling fresh mint leaves before shaking the concoction before topping it with soda water. It simply takes too much time in a bar situation. If you're just making one mojito for yourself at home, you're probably fine. Although I can't imagine anyone being satisfied with just one mojito.
The Martini is without a doubt one of the most iconic American cocktails and one of the most famous drinks of all time, thanks to endorsements by famous drinkers like James Bond. Trying to make one yourself can cause a lot of issues, however, despite the deceptively simple ingredients. Gin is the primary ingredient, but only certain types of gin balance well in a cocktail. If your gin is too herbaceous or too citrusy, it won't have the proper effect. The secondary ingredient, dry vermouth, is also easy to mess up, as there are far too many poor quality vermouths on the market. Even if you get the ingredients right, too many people take James Bond's ill-conceived advice: "shaken, not stirred." In fact, shaking your Martini is not the ideal method of preparation, as it will water it down too quickly.
The Mai Tai is one of the most important "tiki" cocktails, and it is a positively transcendent experience to enjoy one perfectly executed. It is sadly difficult to find a properly made Mai Tai these days, however, largely because it seems like nobody actually knows what the right ingredients are anymore! A true Mai Tai requires both white and dark rums as well as Curaçao, lime juice, and the key ingredient: orgeat syrup. There's no need for pineapple juice, orange juice, grenadine, or anything like that.
Like many of the cocktails on this list, a decent Bloody Mary can be approximated by using a store-bought mixer, but making a true Bloody Mary from scratch is quite the feat. Think of the many complex ingredients that go into a Bloody Mary: besides the base of tomato juice and vodka, you have to add some lime juice for acidity, Worcestershire sauce for umami, hot sauce for spiciness, and that just covers the bare minimum. If you're interested in concocting one of the best brunch cocktails, there are countless ways to make a delicious Bloody Mary, but that's exactly what makes it such a difficult cocktail to perfect.
Long Island Iced Tea
The Long Island Iced Tea is a unique cocktail, to say the least. This drink combines equal parts gin, tequila, rum, vodka, and triple sec with sour mix and Coca Cola. In contrast to the many subtle cocktails on this list, the "everything but the kitchen sink" approach has its own unique array of difficulties. Long Islands are often the signature drinks of cheap frat bars in college towns, and this is a reputation that is extremely hard to live down, due to its status as a cocktail that will get you drunk, fast. The only way to attempt to elevate this drink is to use quality spirits and fresh lemon juice instead of sour mix. Add just a little bit of Coke in order to keep the drink from becoming too cloyingly sweet.
Much like the Long Island Iced Tea, the margarita's reputation is its worst enemy. This complex and deliciously sour tequila cocktail is largely unknown, despite being one of the most popular cocktails in America. The reason for this is simple— what most people think of as a margarita, is made with an outrageously sweet sour mix, and is often blended with ice or served with extra fruit flavors (like the infamous strawberry margarita). A true margarita is made with high-quality ingredients like aged Reposado or Añejo tequila, Cointreau, and freshly squeezed lime juice.
The Daiquiri is sort of rum's answer to the margarita: a delicious combination of lime juice and sugar to highlight the unique flavors of the spirit. Unfortunately, daiquiris also suffer from the epidemic of overly-sweet blended, fruity drinks. Daiquiris also have the additional issue of rum's identity crisis in the United States. When most Americans think of rum, they picture a spiced rum like Captain Morgan. While valid in its own way, spiced rum has a variety of added flavors and is a completely different beast from "real" rum. To make a true daiquiri, get yourself some quality dark rum or white rum, and make sure you're using freshly squeezed lime juice.
The Manhattan is one of my personal favorite cocktails, and it's one of the all time hardest cocktails to make. The Manhattan combines some of the most difficult aspects of both the Old Fashioned and Martini cocktails. Like the Old Fashioned, your choice and proper treatment of the core whiskey is of the utmost importance. And just like a Martini, you need to find a quality vermouth (in this case, sweet vermouth) that complements your specific choice of whiskey. To top it all off, you need to find just the right kind of bitters to add the perfect finishing touch to one of the most classic cocktails of all time.
The Commonwealth Cocktail
This final drink is a bit of a special case, because it really is difficult for me to imagine anyone actually attempting to create it. The commonwealth cocktail was invented by Glasgow-based mixologist Mal Spence to commemorate the 2014 Commonwealth Games, and it is undoubtedly one of the hardest cocktails to make due to its sheer complexity. The commonwealth includes a whopping 71 ingredients from all over the world, including Jamaican okra, Namibian prickly pear fruit, and wild Scottish strawberries.