6 Classic Bourbon Cocktails Every Guy Should Know How To Make

Bourbon is referred to as America’s “native spirit.” While a case can be made that rye whiskey has earlier roots in country, there’s no spirit as entrenched in American culture as bourbon (in fact, it was a 1964 congressional resolution that put bourbon’s “native spirit” phrasing into the official record). There are a few rules and regulations that make this whiskey style particularly American.

First of all, to be considered a bourbon, the whiskey must be made in the United States. Even though your Pappy-loving uncle from Louisville would have you believe otherwise, not all bourbon must be made in Kentucky. Sure, roughly 95 percent of all bourbon is made in the Blue Grass State, but there are also award-winning, complex, memorable bourbons coming out of Wyoming, New York, Texas, and even Florida. So, try what Kentucky offers, but broaden your horizons as well.

The other important rule is in regard to the mash bill and aging. To be considered a bourbon, it must have a mash bill of at least 51 percent corn (with many having a much higher percentage). The rest is filled out with barley, rye, and wheat. The raw spirit then must spend at least two years in never-before-used charred American oak barrels. This is why, when matured in charred oak barrels, bourbon has that memorable sweet corn, vanilla, caramel, and oak flavor that whiskey drinkers crave.

There are a flurry of other specific rules on distillation techniques, alcohol levels, and barrel sizes that distillers must follow. But it’s the ingredients and the aging qualifications that most define that classic bourbon flavor.

Due to these, bourbon is a great base for many whiskey cocktails. It’s bold, rich, and complex enough to stand out even when paired with the most flavorful ingredients. There’s a reason bourbon is the base for some of the most iconic classic cocktails ever made.

One of the most popular whiskey cocktails in the South, the mint julep has strong ties to the Kentucky Derby. This is because it was named the official cocktail of the horse race in 1939. It’s a drink worth enjoying all year long though, with ingredients that include bourbon, water, sugar (or simple syrup), crushed ice, and fresh mint leaves. Herbal, sweet, and refreshing on a hot day–or any day for that matter.

Preparation: Muddle mint, sugar, and water in a highball glass. Add crushed ice and bourbon. Stir to combine. Add a mint sprig garnish.

The paper plane falls into the realm of modern classics. It was created in 2008 by famed bartender Sam Ross for the Violet Hour in Chicago. The drink is made with bourbon, Aperol, the bitter Italian digestif Amaro Nonino Quintessentia, and fresh lemon juice. It’s a combination of sweet, bitter, and fresh citrus flavors.

Preparation: Add all the ingredients to an ice-filled shaker. Shake vigorously. Strain into a chilled coupe glass. Garnish with a lemon twist.

There are no bourbon (or whiskey in general) cocktails more famous than the classic old fashioned–and there are many worthy old fashioned variations and spinoffs. The drink was purportedly invented in 1889 at Louisville’s Pendennis Club by distiller James E. Pepper. The earliest reference to the drink was in 1895 in Modern American Drinks by George Kappeler. Regardless of when it was invented and how old it is, this drink is made with bourbon, water, sugar, and Angostura bitters.

Preparation: Add the sugar to an old-fashioned glass. Add the bitters and water. Muddle it all until the sugar dissolves. Add ice and top with bourbon. Garnish with a cocktail cherry and an orange peel.

Named for the iconic Los Angeles restaurant, the Brown Derby was created at Hollywood Reporter founder Billy Wilkerson’s Vendôme Club in 1930. This simple, flavorful drink consists of bourbon, honey syrup (or simple syrup), and fresh-squeezed grapefruit juice. It’s the perfect combination of tart citrus, sweet sugar, and complex bourbon.

Preparation: Add the bourbon, honey syrup, and grapefruit juice to an ice-filled shaker. Shale vigorously. Strain it into a cocktail glass. Garnish with a grapefruit peel.

This timeless classic was invented in Paris in the early 1920s by American journalist and Vanderbilt family member Erskine Gwynne. Like many classic cocktails, it had a resurgence during the cocktail renaissance of the early aughts. It’s similar to a classic negroni made with Campari, gin, and vermouth, but this drink swaps out the botanical gin for sweet, oaky bourbon.

Preparation: In an old-fashioned glass filled with ice, stir the bourbon, Campari, and sweet vermouth until combined. Strain the drink into another ice-filled glass and garnish with an orange peel and cocktail cherry.

While there are different stories about the origins of the Manhattan, many believe that it was created in the 1870s at the Manhattan Club in New York City by a bartender named Iain Marshall. Often made with rye whiskey because of its spicy, peppery kick, many drinkers opt for the use of bourbon instead to add extra sweetness. Angostura bitters and sweet red vermouth complete the beloved flavor profile.

Preparation: Add bourbon, vermouth, and bitters to an ice-filled glass. Stir to combine. Strain into a chilled coupe glass. Garnish with a cocktail cherry.