The Lion's Tail: A Tropical Cocktail for Bourbon Lovers

The sour cocktail formula (2 ounces spirit, ¾ ounce sweetener, and ¾ ounce citrus) is the key to countless classics, including but not limited to the Whiskey Sour, Gin Sour, Gimlet, and Daiquiri. With a few subtle tweaks, though, a whole new world of drinks is unlocked.

One cocktail that riffs on that template is the Lion’s Tail, a bourbon-based drink made with lime juice, rich simple syrup, allspice dram, and a dash of Angostura bitters. In a way, the Lion’s Tail answers the question of what a bourbon-based Daiquiri would look and taste like.

“It really does bridge that gap of hitting the Venn Diagram gap between classic cocktails, tiki cocktails, and bourbon cocktails,” says SC Baker, bar lead at Louisville’s Epiphany. “There aren’t a lot of drinks that fit all of those categories.”

Twisting the Lion’s Tail

Like many cocktails developed in the first half of the 20th century, the Lion’s Tail’s origin story is a tad murky. What we do know is that the drink first appeared in print in the “Café Royal Cocktail Book,” published in 1937. The book was penned by William James Tarling, who served as the president of the UK Bartender’s Guild and bartended at London’s Café Royal with his brother Arthur, but alongside the Lion’s Tail’s recipe is a blurb that reads “Invented by L. A. Clarke,” with no further context. Who exactly L. A. Clarke was, unfortunately, remains a mystery.

The name of the cocktail is likely derived from the phrase “twisting the lion’s tail,” which was a common, now-antiquated American phrase for provoking the British, whose coat of arms features a lion. The expression emerged between World Wars amidst a stateside swell of Anglophobia and disdain for the empire. It’s thus generally assumed that L. A. Clarke was an American bartender who moved to the UK to continue working during Prohibition. This belief is reinforced by the fact that the drink combines America’s flagship spirit with two ingredients that hail from countries under British rule at the time (Trinidad and Jamaica).

One of those components—and arguably the drink’s defining feature—is allspice dram, a traditional Jamaican liqueur made by infusing rum with dried pimento berries. The resulting liquid is a profoundly dry liqueur with notes of nutmeg, clove, and cinnamon.

Mastering the Lion’s Tail

The drink, in its original form, is a very dry cocktail due to its inclusion of a ½ ounce of allspice dram. While there’s nothing wrong with that, Baker recommends dialing down the allspice and upping the sugar syrup to make a more balanced drink. The original recipe also calls for gomme syrup, but a 2:1 rich simple syrup makes a fine—and easier to make—substitute.

“The allspice can be overwhelming, depending on your palate,” she says. “So I usually do about a fat quarter [generous ¼-ounce pour] of allspice dram, and then I do a fat quarter of a rich simple syrup to give it a little more body and help soften the angularity of the allspice.

Of course, the Lion’s Tail’s base spirit, bourbon, is also going to be a huge flavor-driver. It’s a vast category these days, but Baker insists that the expression one chooses should stand up to the drink’s spice while also preventing it from leaning too dry. In her eyes, that means steering clear of wheated bourbons or anything with a sky-high proof.

“Since it’s playing with allspice, you really want to get something that has a little bit more of a lively composition to it,” she says. “I tend to reach for high-rye bourbons, or bourbons that have a really nice baking spice presence, whether it’s coming from the rye or from the oak itself. I also think that a bourbon in the 90 to 115-proof range is going to be the sweet spot for this cocktail where you’re still standing up to dilution and the flavor of the allspice, but you’re not blowing out your palate with the high heat.”

Given these parameters, her top pick is Russell’s Reserve 10 year old, bottled at 45% ABV, and it contains 13% rye in the mashbill. The bourbon also hails from Wild Turkey, which uses No.-4 char barrels, ensuring the maximum expression of oak character.

For something a bit less conventional, Baker suggests swapping in a cask-finished bourbon. She suggests an amburana cask-finished expression for a cinnamon roll-adjacent profile. And for a Lion’s Tail that leans a bit sweeter, she’s reaching for Green River’s new honey-finished bourbon.

“The Green River Honey is a touch sweet, but it’s still 92-proof,” she says. “If you don’t want to add a lot of sugar to the cocktail, that bourbon has a little bit more of a rounded shoulder on it that helps balance out some of the drink’s spice.”

But don’t feel the need to limit the base to just bourbon. Try splitting it with a high-ester Jamaican rum for some added notes of overripe banana. Toss in a bit of amontillado sherry to amplify the drink’s spice and nuttiness. If you’re a fan of Black Manhattans, Baker suggests adding a splash of Cynar into the build. For a Christmas version, try using a cinnamon syrup in place of the standard rich simple syrup. Alternatively, play around with different bourbons in the build and find which one suits your palate best.

“The drink is quite simple in its construction, so I think that a really fun way to do something whimsical with it is to see what notes in a whiskey really pair well with the allspice,” she says. “You’ll be surprised how versatile the flavor combinations can be.”

Original Lion’s Tail Recipe

• 2 oz. bourbon
• ½ oz. allspice dram
• ½ oz. lime juice
• 1 tsp. gomme syrup
• 1 dash Angostura bitters

Add all ingredients to a cocktail shaker with ice. Shake until chilled. Strain into a chilled coupe.

SC Baker’s Lion’s Tail

• 2 oz. Russell's Reserve 10 year old (or other well-aged high-rye bourbon)
• ¼ oz. allspice dram
• ½ oz. lime juice
• ¼ oz. 2:1 rich simple syrup
• 1 dash Angostura bitters
• Lime twist for garnish (optional)

Add all ingredients to a cocktail shaker with ice. Shake until chilled. Strain into a chilled coupe. Garnish with lime twist.