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A history of Bourbon in four cocktails

Bourbon is the star of some of the world’s oldest classic cocktails – and one of its newest cult favourite spirits. Alicia Miller charts bourbon’s mixology history in four iconic pours

Mint Julep 1700-1800s

In America’s southern states, people self-medicated with alcoholic pours as far back as the 18th century, when stomach-soothing ‘juleps’ (derived from the Arabic word julab) featured alcohol steeped with mint. Given that bourbon itself didn’t emerge much earlier – and production only accelerated decades later with increased maize plantings and barrel-based transport – early renditions would have been made with rye.

Thanks to local fans (Kentucky senator Henry Clay, Mississippi writer William Faulkner) plus its association with the Kentucky Derby horse race, where the drink has been officially served since the 1930s, Mint Juleps are inextricably linked with the whiskey of the South. Every year, the Derby (sponsored by Woodford Reserve) serves nearly 120,000 cocktails – made with speedy just-add-ice Old Forester Mint Julep.

When choosing a bourbon for home mixing, the most important factor is abv: don’t go much lower than 47%, or it will dilute unpleasantly as the ice melts. Select a quality spirit – remember, you’ll really taste the bourbon here – and go easy on the sweetener.

Mint Julep

Glass Julep cup or highball

Garnish 3 mint leaves; straw

Ingredients 85ml bourbon, 21ml simple syrup, 8-10 very fresh mint leaves

Method Pack the cup with crushed ice. Combine ingredients in a mixing glass. Using a muddler, lightly bruise the mint, then strain contents into the cup. Garnish with 3 large mint leaves (slap between your palms first to release aromas) and a straw.

Old Fashioned 1870s-1880s

It’s the very definition of a cocktail, as first laid out in print in 1806: alcohol, sugar, water, bitters. Originally known as a Whiskey Cocktail, the Old Fashioned tag likely stuck some time in the 1870s or 1880s, when bartenders started making ‘improved’ versions with alternative spirits, drawing a distinction from the original, or ‘old fashioned’ style.

As with Mint Juleps, rye would have been the original base, but whether through evolution or an association with Kentucky’s Pendennis Club (at one time thought to be the inventor of the drink), bourbon is now the typical pour. The cocktail’s ubiquity has given birth to much variation over time – sugar syrup rather than cubes, muddled fruit, quirky bitters – but post-Mad Men-revival, a simple serve with quality sipping bourbon and a simple orange twist has become standard.

Ask 10 bartenders for their choice bourbon and you’ll get 10 different answers, from Evan Williams Single Barrel – preferred by award-winning Ryan Chetiyawardana – to modern classic Buffalo Trace, used in the likes of London’s oldest restaurant, Rules.

Old Fashioned

Glass Rocks

Garnish Orange twist

Ingredients 60ml bourbon, 2 dashes Angostura aromatic bitters, 1 brown sugar cube

Method Place the sugar cube in a glass; wet with bitters and a small dash of water. Crush with a muddler and stir until well combined. Add a large ice cube to the glass and pour over whiskey; stir. Garnish with orange twist.

Boulevardier 1920s

Prohibition in the 1920s was a major blow to the bourbon industry, but that didn’t stop it being enjoyed abroad. New York bartender Harry MacElhone relocated to London then Paris, where he set up Harry’s New York Bar to mix pre-Prohibition cocktails and new drinks with European ingredients. His 1927 Barflies and Cocktails guide featured the Boulevardier, the signature drink of his friend Erskine Gwynne, an expat American writer who edited the monthly magazine after which the drink is named.

Effectively a cousin to the Negroni, the original recipe called for equal parts Campari, sweet vermouth and bourbon. These days, the whiskey ratio is often increased, lending an alcoholic kick and refined balance – but, ultimately, this should depend on your vermouth, and your bourbon of choice (many modern bartenders, in fact, prefer rye for its spicy kick).

To honour both flavour and history, use a bourbon with a high rye content to bring complexity and grown-up taste to balance the sweetness. As well as those listed, Bulleit is a winner.


Glass Rocks

Garnish Orange twist

Ingredients 40ml bourbon, 20ml Campari, 20ml sweet red vermouth

Method Combine ingredients in a mixing glass with ice, then stir until cold. Strain into a glass immediately and serve with a large ice cube. Garnish with an orange twist.

Paper Plane 2007

The most famous modern-day bourbon cocktail isn’t about bourbon at all. In 2007, bartender Sam Ross, of New York’s Milk & Honey, created a cocktail for the summer menu of friend Toby Maloney’s Chicago bar, The Violet Hour. Obsessed with little-known Amaro Nonino, he tried combining the traditional herbal liqueur with different spirits, in a simple equal-parts formula similar to the gin-based Last Word. Ross eventually landed on bourbon because of its ‘big body, extra sweetness and caramel notes’, and his easy-to-mix Paper Plane took off on social media and in bars worldwide.

While a premium bourbon won’t hurt (we love it with Baker’s 7 Year Old, if you’re splurging), Ross swears it won’t make much difference. The key things are the abv – 45% or above, he says, to get the balance right – and a high corn content, as it brings richness. His go-to, Buffalo Trace, sells at a lower 40% abv in the UK – so unless you can get hold of a higher-proof American bottling, try one of those listed.

Paper Plane

Glass Coupe

Garnish None (lemon zest twist optional)

Ingredients 20ml bourbon, 20ml Amaro Nonino, 20ml Aperol, 20ml lemon

Method Add all ingredients to a shaker. Fill completely with ice, shake vigorously, then strain immediately into the glass. You’ll know you’ve shaken hard enough if there’s a light foam on top of the cocktail.

Straight talk: the best bourbons for mixing

Maker’s Mark 46

Rich nose of toasted oak and vanilla from seared French staves; an equally intense palate – here’s a buttery, complex bourbon that can withstand the ice melt of a Mint Julep. Solid abv. Alcohol 47%

Four Roses Single Barrel

This high rye content, high-alcohol bourbon really blossoms in a Mint Julep as the ice melts. Honeyed notes keep on giving, along with fruity complexity and enduring cinnamon spice, backed by a long finish. Alc 50%

Woodford Reserve

Triple distilled for smooth drinking, this thick honey- and vanilla-noted bourbon is perfect for Old Fashioned newbies. Cocoa, espresso and orange peel hints on the palate, thanks to the moderate rye percentage, add interest. Alc 43.2%

New Riff Distilling Bottled in Bond

Old Fashioneds allow premium bourbons such as New Riff to shine. Made with non-GMO grains, this rye-forward bottling has aromas of clove, dark berries and oak. Alc 50%

Basil Hayden’s

A rye-heavy mash bill gives a spicy, savoury kick, ideal for Boulevardiers. Light, with Christmas pudding spices on the nose and palate; some crystallised ginger and menthol. Alc 40%

Old Forester 1870 Original Batch

Cinnamon, clove, menthol, vanilla and apple. The original is often used in Mint Juleps, but the extra proof, spice and complexity of this bottling make it a great fit for premium Boulevardiers when paired with high-quality vermouth. Alc 45%

Michter’s US*1

Paper Plane recipe creator Sam Ross names this as a favourite, alongside Buffalo Trace: a decent alcohol content adds weight, while a high corn mash bill brings roundness. Caramel, dried fruits and butterscotch on the nose and palate. Alc 45.7%

Knob Creek

Punchy abv, sweet and hazelnutty corn character – this small-batch bottling from Jim Beam, made with a unique strain of jug yeast, adds weight to a Paper Plane. Alc 50%

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