The Lion’s Tail: A Complete History & Classic Recipe

The year is 1937. A sleek art deco bar hums somewhere between the Great Depression and the Jazz Age. In the glass before you: a dark, spicy, aromatic mixture swirling with promise — bourbon, lime, and a mysterious liqueur from Europe that had only recently become available again after Prohibition.

It smells like oak and cinnamon, clove and citrus peel. You take a sip — and it’s both familiar and exotic, a bourbon sour with a sly botanical twist.

This is the Lion’s Tail, a cocktail that defied convention, marrying American whiskey with European spice during one of the most creative and uncertain periods in drinking history. Once nearly forgotten, it’s now regarded as one of the great “lost classics” of pre-war cocktail craft.

I. Origins

The Lion’s Tail first appeared in print in 1937 in the Café Royal Cocktail Book, compiled by William J. Tarling — one of the most influential post-Prohibition bartending manuals.

The recipe called for bourbon, lime juice, simple syrup, bitters, and pimento dram — the Jamaican allspice liqueur that gave the cocktail its unmistakable spice.

The Context

At the time, American whiskey was enjoying a global renaissance. With Prohibition lifted in 1933, distilleries were rebuilding, and bartenders were rediscovering the nuances of American spirits. Meanwhile, London’s Café Royal — a meeting place for expatriate bartenders who had honed their craft during the dry years — was a laboratory for cross-Atlantic experimentation.

Into this creative melting pot came the Lion’s Tail: an Anglo-American hybrid that fused Kentucky bourbon with Caribbean spice and British elegance.

II. Historical Evolution

1930s: The Original Era

The Lion’s Tail reflected the adventurous spirit of the late 1930s. Bartenders were exploring flavor combinations that spanned continents — a reflection of the globalism that defined interwar cocktail culture.

The key ingredient, pimento dram, had long been a staple in Caribbean and colonial punch recipes. Made from allspice berries (called pimento in Jamaica), it offered warmth, depth, and mystery. Combined with bourbon’s vanilla-caramel tones, it produced a profile unlike anything else in mixology.

Postwar Obscurity

After World War II, the Lion’s Tail disappeared from mainstream cocktail lists. Pimento dram became difficult to source outside the Caribbean, and bourbon itself fell out of fashion as gin, vodka, and rum rose in popularity.

The Craft Revival

When the craft cocktail movement took off in the 2000s, mixologists like Ted Haigh (Dr. Cocktail) and David Wondrich rediscovered the recipe in Tarling’s 1937 book. With modern small-batch distilleries reintroducing pimento dram (notably St. Elizabeth Allspice Dram), the Lion’s Tail roared back to life — reclaiming its place among the great spiced whiskey cocktails.

Today, it’s admired for its boldness: a drink that fuses the sweetness of bourbon with the heat of allspice and the tang of lime — a true bridge between continents and styles.

III. Ingredients & Technique

The Lion’s Tail is a whiskey sour at heart, but the addition of pimento dram transforms it completely.

Core Components:

• Base Spirit: Bourbon (occasionally rye for a spicier edge).

• Citrus: Fresh lime juice — adds acidity and freshness.

• Sweetener: Simple syrup — softens the citrus bite.

• Modifier: Pimento dram (allspice liqueur) — the defining element, warm and aromatic.

• Bitters: Angostura — adds structure and a subtle bridge to the allspice.

The secret: The dram must be used sparingly — too much, and it dominates. Just half an ounce transforms the drink without overwhelming it.

IV. Cultural Significance

The Lion’s Tail embodies a turning point in cocktail history — the global fusion of ingredients long before “globalization” was a buzzword. It’s a drink born from connection: American bourbon meeting Caribbean spice in a British bar during a world between wars.

Its rediscovery also highlights the cyclical nature of cocktail culture. Lost for decades, the Lion’s Tail became a symbol of how historical research and modern craftsmanship can breathe life back into forgotten classics.

Culturally, it resonates with our era as much as its own — a celebration of diversity, heritage, and the enduring magic of rediscovery.

V. How to Make the Classic Version Today

Recipe — The Classic Lion’s Tail

Ingredients

• 2 oz (60 ml) Bourbon whiskey

• ½ oz (15 ml) Pimento dram (allspice liqueur)

• ½ oz (15 ml) Fresh lime juice

• ½ oz (15 ml) Simple syrup (1:1)

• 2 dashes Angostura bitters

Method

1. Add all ingredients to a shaker with ice.

2. Shake vigorously for 10–12 seconds.

3. Strain into a chilled coupe or Nick & Nora glass.

4. Express an orange peel over the top (optional).

Specs

• Glass: Coupe or Nick & Nora

• Ice: None (served up)

• Garnish: Orange twist or lime wheel

• Style: Spiced whiskey sour

Technique Notes

• Don’t overuse the pimento dram — it’s powerful. ½ oz is the upper limit.

• Balance acidity: adjust lime and syrup based on bourbon sweetness.

• For a smoother profile, use a wheated bourbon; for bolder spice, choose rye.

Variations & Lineage

• Rum Lion: Substitute aged Jamaican rum for bourbon — tropical and aromatic.

• Lion’s Mane: Add a bar spoon of honey syrup for rounder sweetness.

• Winter Tail: Incorporate a splash of apple cider or cinnamon syrup for seasonal warmth.

Service & Pairing Tip

• Best enjoyed as an after-dinner drink or fall cocktail.

• Pairs beautifully with pecan pie, roasted nuts, or dark chocolate.

VI. Modern Variations & Legacy

The Lion’s Tail is now considered a revived classic — one that bridges old-world and new-world sensibilities. It’s rich, aromatic, and perfectly emblematic of the cocktail renaissance’s fascination with rediscovery.

Modern bartenders often riff on its structure: swapping pimento dram for amaro, infusing bourbon with baking spices, or serving it over ice for a more casual presentation.

What endures is its balance of contrasts:

• Sweet yet tart.

• Warm yet refreshing.

• Familiar (bourbon sour) yet exotic (Caribbean spice).

It remains one of the most rewarding “bartender’s cocktails” — deceptively simple, endlessly expressive.

As historian Ted Haigh wrote, “The Lion’s Tail proves that the past was never boring — we just forgot to look hard enough.”