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The first half of this list is “bartender’s choice” cocktails, contemporary creations that come straight from the cocktail shakers of today’s top bartenders. The second half is classics, both pre-Prohibition standards and more modern ones that have achieved worldwide acclaim. You’re sure to find something for every palate among these 20 drinks.
Some purists will argue that bourbon is best consumed neat, but we beg to differ. When combined with different supporting elements, bourbon’s varied sides to its complex flavor profile are able to be appreciated more fully. Whether you like it spirit-forward in a classic Old Fashioned, sweetened in a fruity punch or heated up in a Hot Toddy, there’s a bourbon drink to satisfy every palate.
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Peach Me
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Peach schnapps makes an unexpected appearance in this riff on an Old Fashioned. Muddle a Luxardo maraschino cherry, an orange slice and a few dashes of orange bitters together, then shake with ice, bourbon and the schnapps until well-chilled. Strain over a large ice cube and serve with an orange slice, dehydrated or fresh, for extra pizzazz.
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Forbidden Sour
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Pomegranate liqueur adds a sultry element to this take on a Whiskey Sour by bartender Eben Freeman. Add it to your shaker along with the usual bourbon, lemon juice and simple syrup, and finish it off with an orange wheel and preserved cherry to enhance the fruity flavors.
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Downhill Daring
Hailey Sadler Inspired by the classic Brooklyn cocktail, this Reverse Manhattan riff sees bourbon combined with Punt e Mes, Benedictine, Cocchi Americano and Angostura and orange bitters. Stir it all together with ice until well-chilled, and garnish with an expressed orange twist.
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Billionaire
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A favorite from New York City’s popular Employees Only, this cocktail—a sleeker version of the pre-Prohibition Millionaire, itself a gussied-up Whiskey Sour—is well on its way to becoming a modern classic. Add grenadine and absinthe bitters to the bourbon, lemon juice and simple syrup, and garnish with a lemon wheel after shaking.
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Expense of Honesty
Ashley Hylbert This Old Fashioned riff splits the difference between several elements. It combines bourbon with two types of rum, uses honey as well as sugar and employs both Peychaud’s and Angostura bitters. That’s one way to make everyone happy.
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Rancor’s Toothpick
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Straight from Brooklyn’s Long Island Bar, this Boulevardier riff will take you from cranky to calm in a mere sip, even if you’re feeling as rattled as a gnarly-toothed rancor in “Star Wars.” It sees Cynar swapped in for the usual Campari and mole bitters used in place of Angostura.
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Amaretto Sour
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What’s this doing out of the “classics” category, you ask? This version of the drink, created by Portland bartender Jeffrey Morgenthaler, is such an improvement on the dive bar standard that it basically counts as an entirely separate cocktail. Shake together amaretto, cask-proof bourbon, lemon juice, rich simple syrup and egg white, and garnish with a lemon twist and two brandied cherries. You’ll never reach for premade sour mix again.
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What’s Up, Doc
SaltRock Southwest Kitchen Add a little bourbon to your juice cleanse. This cocktail makes the most out of nature’s bounty to highlight bourbon’s complex flavors. Shake fresh carrot-ginger juice, bourbon, Fernet-Branca and fresh lemon juice with ice, then strain and serve with a rosemary or thyme sprig.
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Beggar’s Banquet
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Not only can you build this cocktail right in the glass, it’s delicious to boot. Bourbon, maple syrup, lemon juice and chilled lager come together to create an effervescent drink that proves that bourbon and beer can play nicely together when combined in the right way.
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Old Fashioned
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The key to this classic is using high-quality bourbon. If it’s something you wouldn’t drink on its own, then it won’t work well as the star in this drink. The recipe is simple: Just combine sugar, bitters and water, then stir with bourbon and ice before garnishing with an expressed orange peel.
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Hot Toddy
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This grandfather of hot cocktails is perfect when you want something to warm you from the inside. The mix of boiling water, sugar, lemon juice and bourbon is the perfect whiskey-fueled embrace you need once sweater weather starts.
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Mint Julep
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This drink isn’t just for the Kentucky Derby. It’s so refreshing and easy to make that it deserves to be a year-round staple. Muddle together mint and simple syrup, then top with bourbon and crushed ice and stir until the cup is frosted. Garnish with bitters and a mint sprig.
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Whiskey Sour
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With a history that stretches back to the Lincoln administration, it’s no wonder that this simple combination of spirit, citrus and sugar has stuck around for so long. After all, how could a fluffy mix of bourbon, lemon juice, simple syrup and egg white not instantly charm anyone who tastes it?
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Manhattan
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One of the best-known and most popular cocktails in the whiskey canon, the Manhattan is the perfect spirit-forward sipper that every bourbon lover should know how to make. While it’s commonly thought of as a rye-based drink, bourbon’s smoother and mellower qualities play just as nicely among the vermouth and bitters. Stir it all until well-chilled and garnish with a brandied cherry.
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Boulevardier
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One of many Negroni spin-offs and nearly as beloved in its own right, the Boulevardier is a balanced combination of bitter, boozy and sweet. Equal parts bourbon, Campari and sweet vermouth are all you need. Just stir with ice until nice and chilled, then garnish with an orange peel.
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Brown Derby
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Named for the eponymous hat-shaped Los Angeles diner, this cocktail has all the glamour of old Hollywood. Shake bourbon, fresh grapefruit juice, honey syrup and ice together, then strain and garnish with a grapefruit peel after expressing the oil or a fresh grapefruit wedge.
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Gold Rush
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This cocktail, created at Milk & Honey in the early aughts, has spread worldwide at such a pace that it’s commonly assumed to be a pre-Prohibition classic. The three-ingredient tipple is a beautiful honey-soaked version of the Whiskey Sour. Bourbon, honey syrup and fresh lemon juice are all you need.
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Paper Plane
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Though it has only been around since 2007, this modern creation—also a Milk & Honey drink—inspired by the Last Word has been embraced by bartenders and drinkers as a true classic in the making. Equal parts bourbon, Aperol, amaro and lemon juice come together to make a cocktail that hits a balance between bitter, sour and herbal notes.