13 classic bourbon cocktails you need to try, according to a mixologist

Table of Contents: Masthead Sticky

• Bourbon is a popular base for cocktails with popular recipes dating back to the early 1800s.
• Bourbon works well in both simple cocktails like the old fashioned and citrusy.
• Use bourbon with a high proof and high rye content so it holds up next to the other ingredients.
• Visit Insider's Home & Kitchen Reference library for more stories.

The origins of the modern cocktail can be traced back to the United States in the early 1800s – to the original recipe for the old fashioned – and there is no spirit more closely associated with American history than bourbon.

Bourbon (and, more broadly, whiskey in general) continues to be a popular base for cocktails to this day. "Rye, Scotch, Irish, bourbon, they all mix well and they don't lose their characteristics," says bartender, mixology YouTuber, and self-described "spirit guide," Anders Erickson. "Whiskey is something that can stand on its own, or you can mix a little bit of something or a lot of something, and it's still going to balance out okay."

Because of the spirit's rich history, there are so many bourbon cocktails to try. It can be tough to know where to start. To help, here's a list of classic recipes approved by Erickson along with a few more new-school favorites.

1. Manhattan

The Manhattan is one of the most well-known classic cocktails. It's named after the Manhattan Club, where it was invented in the 1880s. Mix the bourbon, vermouth, and bitters with ice in a mixing glass and stir to incorporate. Strain and pour into a chilled coupe or martini glass. Garnish with Luxardo cherries and/or a twist of orange peel.

2. Old fashioned

With its first published recipe dating back to 1806, the old fashioned is one of the oldest known cocktails. "I love an old fashioned with bourbon. A little bit of sugar and bitters really complements the spirit," Erickson says. To make one, put all of the ingredients in a mixing glass with ice and stir. Strain into a rocks glass over ice and garnish with a twist of orange peel. To enhance the aroma from the orange, rub the peel around the rim of the glass and squeeze the oils in the skin over the top of the cocktail.

3. Kentucky buck

Cut the stem off of a strawberry and muddle it in a cocktail shaker. Add the bourbon, lemon juice, and simple syrup, and shake with ice. Strain into a glass over ice, making sure to leave some room. To finish, top the cocktail off with ginger beer and add a sliced strawberry for garnish.

4. Mint julep

The mint julep is most famous for being served at Churchill Downs during the Kentucky Derby, but it's a cool and refreshing drink perfect for hot weather. To make, shake the bourbon, mint leaves, and simple syrup with ice. Fill the serving cup a bit more than halfway with crushed ice. Then strain the mixture over the ice and top with more ice. Serve with a straw and a few sprigs of fresh mint as garnish. The crushed ice makes a huge difference for this drink. The smaller pieces of ice keep the drink extra cold, giving the traditional metal cup that classic layer of frost.

5. Boulevardier

This classic cocktail is sometimes referred to as a bourbon Negroni because of its similar ingredients and presentation. To make this, pour the bourbon, Campari, and vermouth into a mixing glass and stir. Strain into a rocks glass over a large piece of ice and garnish it with an orange peel.

6. Lion's tail

This Erickson-recommended cocktail dates back to the 1930s. The term "to twist the lion's tail" meant to provoke an adversary stronger than you. It referred to the strength of the British, whose coat of arms is adorned with a lion. To make the cocktail, combine all ingredients in a cocktail shaker. Add ice and shake to chill and dilute (about 10 to 15 seconds). Strain into a chilled cocktail glass and garnish with a lime twist (optional).

7. Paper plane

This modern classic was invented by Sam Ross while he was bartending at Milk & Honey in New York City. To make a paper plane, combine equal parts bourbon, Aperol, amaro, and fresh-squeezed lemon juice into a cocktail shaker with ice. Shake to mix (around 10 to 15 seconds) and strain into a chilled glass.

8. Whiskey sour

"Bourbon works well with citrus because you've got this bright, acidic sharp flavor along with the bold, rich slightly sweet bourbon," Erickson says. "Sweet bourbon with bright citrus is, in most cases, outstanding." Mix all four ingredients in a cocktail shaker with ice and shake vigorously. Strain into a chilled glass to serve. Use fresh-squeezed lemon juice if possible. The egg white is optional but adds body and creaminess to the cocktail when shaken with the other ingredients.

9. Stone fence

To make, mix the bourbon, cider, and bitters in a serving glass, and then fill the glass with ice. Garnish with a thinly sliced piece of apple. This cocktail is rumored to have had its genesis during the American Revolutionary War and remains a popular fall cocktail due to the inclusion of apple cider and the spicy flavor notes from the bourbon and bitters.

10. Brown derby

This cocktail is named after the iconic Old Hollywood restaurant, The Brown Derby. To make this drink, mix the bourbon, grapefruit juice, and honey syrup in a shaker with ice. Strain and pour into a chilled coupe glass. Make your own honey syrup by combining two parts honey and one part water and warming it in a saucepan until the honey is completely dissolved. For a richer honey syrup, increase the ratio to three to one.

11. Whiskey smash

The whiskey smash is another classic that can trace its origin back to the late 1800s. To make this refreshing cocktail, muddle the lemon in a shaker, then add the simple syrup, mint leaves, and bourbon and shake with ice. Strain over ice and garnish with a mint sprig. It may share some ingredients with the whiskey sour and mint julep, but it really is its own unique cocktail.

12. Monte Cassino

Another of Erickson's favorites, this drink was created by Damon Dyer in 2010. Originally calling for rye whiskey, bourbon makes for a tasty substitution. To make the Monte Cassino, combine all ingredients in a cocktail shaker. Add ice and shake to chill and dilute (about 10 to 15 seconds). Strain into a chilled cocktail glass. No garnish necessary.

13. Hot toddy

The hot toddy is the perfect cocktail for cold weather. Heat some water to just below boiling. Combine the bourbon and simple syrup in a heat-proof glass or mug and stir to mix. Add the hot water to the glass, stir again to incorporate, and garnish with a lemon wedge.

Insider's takeaway

With such a long and rich history, it's no surprise that there are so many diverse cocktails that can be made with bourbon. Whether you want something sweet and fruity or something drier and more traditional, there's something out there for everyone.

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