The Bootleg Cocktail

By Steve Kilcullen Jump to Recipe

The next time you’re at the local speakeasy, ask the barkeep for a Bootleg or two before they get raided.

When I was a teenager, bootlegs were some of my favorite things to collect. And by that, I mean unofficial musical releases from some of my favorite bands. Local and small record shops or comic book stores would oftentimes have a little section where popular, fan-made recordings would be sold. Many of these were legendary, like certain Led Zeppelin concerts that had a reputation for being unbelievably amazing to hear, whatever the clandestine soundboard recording sounded like. The list goes on and on, and isn’t relegated to just rock bands. Star Trek blooper bootlegs on VHS were like gold back in the 1980s and 1990s to a nerd like me, which you could only get at conventions, sold by someone who duped multiple copies in their basement. And until it was officially released on home media in the mid-1990s, the bootlegs for the 1981 adult animated film Heavy Metal were truly one of the holy grails of geekdom.

Tonight’s drink is named the Bootleg, and rightfully so. Born during the Prohibition era, when alcohol was outlawed and illegal in the United States, the Bootleg cocktail was a mixture that masked the rough, homemade hooch it served while also celebrating righteous lawlessness.

Said to have been born on the shores of Lake Minnetonka in Minnesota during the 1920s, the Bootleg is rumored to have been imbibed by the likes of gangster Al Capone and author F. Scott Fitzgerald. Many establishments in the Land of 10,000 Lakes will say they originally invented the mixture, but like many libations throughout history, these stories are always a little muddled.

Nowadays, spirits are legal again and a tad more palatable than the clandestine sauces of yore. But we can still imagine what those heady days of bootlegging must’ve been like while sipping on a Bootleg of our own.

What is the best alcohol to use in the Bootleg Cocktail?

Depending on your tastes and mood, you can opt for either vodka or gin to craft this cocktail. For the gin, a variety of styles can be used, such as Old Tom and London Dry, to name a few. I always enjoy the latter, with its juniper and citrus infusions providing a lovely herbaceous bite with every sip. For a smoother and softer flavor, a clean and crisp vodka will meld beautifully with the other ingredients, taking on some of their qualities and accentuating them.

What glassware and garnish are used?

Fill a highball glass or collins glass with ice and mix your Bootleg in, stirring gently. Garnish with a fresh lime wheel or two and a sprig of mint on the top.

Can Bootleg mix be store-bought?

The Minnesota-based Summer Lakes Beverage company produces a bottled and premade Bootleg mix that you can purchase from their website, along with a number of other ready-to-make mixers as well.

Similar drinks to the Bootleg Cocktail

While there’s some controversy surrounding many of the mixed drinks that claim to be inventions of the Prohibition era—mainly because some historians have stated that it was mostly champagne that was imbibed at speakeasies, and not cocktails—the myths behind these sweet, tart and strong beverages persist to this very day. Here are a few that still cut through the mists of time.

• Southside – Said to be Al Capone’s favorite illicit beverage.
• Gin Rickey – This D.C. area classic features in the F. Scott Fitzgerald novel The Great Gatsby.
• Bee’s Knees – This speakeasy elixir helped hide the taste of rough and illegal bathtub gin.
• Eastside – A contemporary riff on the gin-based Southside recipe.