Bootleggers Drinks: Uncovering the Fascinating History

Introduction to Bootleggers drinks

Few eras in American history have captured the public’s imagination as vividly as the Prohibition era. During this tumultuous time, a new breed of entrepreneurs emerged, defying the law and risking everything to quench the nation’s thirst for alcoholic beverages. These daring individuals, known as bootleggers, not only supplied the demand but also left an indelible mark on the world of mixology with their ingenious concoctions, now referred to as “Bootleggers drinks.”

The prohibition era and bootlegging

The 18th Amendment to the United States Constitution, ratified in 1919, ushered in a nationwide ban on the production, importation, transportation, and sale of alcoholic beverages. This sweeping legislation, known as the Volstead Act, aimed to curb the perceived societal ills associated with alcohol consumption. However, the unintended consequences were far-reaching, giving rise to a thriving underground market and the proliferation of illegal drinking establishments known as speakeasies.

Bootleggers, the masterminds behind this illicit trade, risked life and liberty to smuggle and distribute alcohol across the country. Their daring exploits and ingenious methods of evasion became the stuff of legends, captivating the public’s imagination and fueling a cultural phenomenon that endures to this day.

Bootleggers Drinks
Bootleggers Drinks

What were Bootleggers drinks?

Bootleggers drinks were innovative cocktails born out of necessity during the Prohibition era. With limited access to quality ingredients and the ever-present threat of law enforcement, bootleggers had to get creative with their concoctions. These drinks often reflected the times, incorporating whatever spirits, mixers, and garnishes were available, regardless of their provenance or quality.

The hallmark of Bootleggers drinks was their ability to mask the harsh, sometimes downright unpalatable, flavors of the illicit liquors they were made from. Bootleggers employed a variety of techniques, such as infusing spirits with fruits, herbs, and spices or adding copious amounts of sugar and other sweeteners to make their wares more palatable.

Bootleggers drinks during the Prohibition era

During Prohibition, speakeasies became the epicenters of Bootleggers drinks, offering a safe haven for those seeking a respite from the dry reality of the times. These clandestine establishments, often hidden behind innocuous storefronts or concealed in basements and backrooms, were where the magic of Bootleggers drinks truly came alive.

Bartenders, or “mixologists” as they were often called, became the alchemists of the era, concocting an array of potent potions that tantalized the taste buds and fueled the revelry. Some of the most iconic Bootleggers drinks from this period include:

  • The Sidecar: A potent blend of cognac, triple sec, and lemon juice, it is said to have been named after the motorcycle sidecar used to transport the illicit liquor.
  • The Bee’s Knees: A delightful combination of gin, honey, and lemon juice, often cited as a prime example of how bootleggers used sweeteners to mask the harsh flavors of bathtub gin.
  • The Scofflaw: A bold and defiant cocktail made with rye whiskey, grenadine, lemon juice, and dry vermouth, named after those who “scoffed” at the law.

Famous bootleggers and their signature drinks

While the Prohibition era gave rise to countless bootleggers, a few names stand out for their audacity, ingenuity, and the iconic drinks they popularized. One such figure was George Remus, the “King of the Bootleggers,” whose empire spanned across several states. Remus was known for his signature cocktail, the “Remus Fizz,” a frothy concoction of gin, lemon juice, and egg white, often garnished with a cherry.

Another notorious bootlegger was Dutch Schultz, whose ruthless tactics and violent reputation were matched only by his love for fine liquor. Schultz is credited with popularizing the “Schultz Sour,” a potent mix of rye whiskey, lemon juice, and egg white, garnished with a cherry and an orange slice. The Schultz Sour became a staple in speakeasies across the country, a testament to Schultz’s influence and the enduring appeal of Bootleggers drinks.

How Bootleggers drinks evolved over time

As the Prohibition era drew to a close in 1933, the world of Bootleggers drinks transformed. With the legalization of alcohol, the once-illicit concoctions found their way into the mainstream, becoming celebrated cocktails in their own right.

Bartenders and mixologists, no longer bound by the constraints of the underground, began to refine and elevate these drinks, experimenting with higher-quality ingredients and innovative techniques. The result was a renaissance in the world of mixology, with Bootleggers drinks serving as the foundation for a new era of cocktail culture.

One of the most notable evolutions was the emergence of the “speakeasy-style” cocktail bar, which sought to recreate the clandestine ambiance of the Prohibition era. These establishments became havens for cocktail enthusiasts, offering meticulously crafted Bootleggers drinks alongside a nostalgic nod to the era that birthed them.

Bootleggers Drinks
Bootleggers Drinks

Modern interpretations of Bootleggers drinks

In recent years, the fascination with Bootleggers drinks has experienced a resurgence, with contemporary mixologists drawing inspiration from the ingenuity and resourcefulness of their Prohibition-era predecessors. These modern interpretations often pay homage to the classics while incorporating contemporary techniques and innovative ingredients.

A drink like this is the “Smoked Maple Old Fashioned,” which is a variation of the traditional Old Fashioned that has smoked maple syrup and bitters added to it. It evokes the smoky flavors of illicit whiskeys once distilled in backwoods stills.

Another popular modern interpretation is the “Lavender Bee’s Knees,” which puts a floral spin on the classic Bee’s Knees cocktail by infusing the gin with lavender and adding a touch of honey syrup. This creates a delightfully aromatic and refreshing libation.

Popular Bootleggers drinks recipes

For those seeking to recreate the magic of Bootleggers drinks at home, there are countless recipes to explore. Here are a few popular and easy-to-make Bootleggers drinks that capture the essence of the era:

The Sidecar

  • 2 oz cognac
  • 1 oz triple sec
  • 1 oz fresh lemon juice
  • Lemon twist for garnish


  1. Fill a cocktail shaker with ice.
  2. Add cognac, triple sec, and lemon juice.
  3. Shake vigorously for 10-15 seconds.
  4. Strain into a chilled coupe glass
  5. Garnish with a lemon twist.

The Bee’s Knees

  • 2 oz gin
  • 1 oz fresh lemon juice
  • 1 oz honey syrup (equal parts honey and water)
  • Lemon twist for garnish


  1. Put everything into a cocktail shaker that has ice in it.
  2. Mix vigorously for 10-15 seconds.
  3. Strain into a chilled coupe glass
  4. Garnish with a lemon twist.

The Scofflaw

  • 2 oz rye whiskey
  • 1 oz dry vermouth
  • 1 oz lemon juice
  • 1 tsp grenadine
  • Lemon twist for garnish


  1. Fill a cocktail shaker with ice.
  2. Add rye whiskey, dry vermouth, lemon juice, and grenadine.
  3. Shake vigorously for 10-15 seconds.
  4. Strain into a chilled coupe glass
  5. Garnish with a lemon twist.

With these recipes, you can get a tantalizing taste of the creative and resourceful drinks that bootleggers used, taking you back to the speakeasies of the Prohibition era.

The legacy of Bootleggers drinks

The impact of Bootleggers drinks on modern cocktail culture cannot be overstated. These once-illicit concoctions have transcended their clandestine origins, becoming celebrated and revered by mixologists and cocktail enthusiasts alike.

Beyond their influence on the world of mixology, Bootleggers drinks have also left an indelible mark on popular culture. From films and television shows depicting the Prohibition era to themed cocktail bars and speakeasies, the allure of Bootleggers drinks continues to captivate audiences worldwide.

Moreover, the legacy of Bootleggers drinks reminds us of the resilience and ingenuity of the human spirit. In the face of adversity and legal restrictions, these enterprising individuals found a way to not only quench the nation’s thirst but also create a lasting cultural phenomenon that continues to inspire and delight generations of imbibers.


The History of Bootleggers Drinks is a captivating tale of defiance, creativity, and the indomitable human spirit. From the smoky backrooms of speakeasies to the modern-day cocktail renaissance, these once-illicit concoctions have stood the test of time, serving as a testament to the enduring allure of the forbidden and the ingenuity of those who dared to defy the law.

As we raise our glasses and savor the complex flavors of a well-crafted Bootleggers drink, we pay homage to the daring individuals who risked everything to quench the nation’s thirst. Their work lives on as an inspiration to mixologists and cocktail fans alike to keep pushing the limits of mixology and making new drinks that capture the spirit of that troubled time.

If you’re a fan of cocktail culture and the rich history behind it, consider joining our exclusive cocktail club. With monthly curated cocktail kits and virtual mixology classes led by renowned bartenders, you’ll have the opportunity to explore the fascinating world of Bootleggers drinks and other iconic cocktails from the comfort of your own home. Sign up today and embark on a journey through the annals of mixology, one delightful sip at a time.

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