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Best Classic Bourbon Cocktails

These days, a cocktail means a boozy punch, possibly spiked with Red Bull and swilled by armies of screaming college girls. Sure, it can be fun to jump around to music that’s too loud while you down plastic cups of colorful, oversweetened drinks spiked with the clear ‘soccer mom’ spirits.

But there was a time when men wore suits no matter what the occasion and smoking was good for you. In those days, a cocktail meant something different. Cocktails came straight out of the prohibition era and they did not to hide the alcohol, but showcased it. They came in tumblers and glasses and you drank them during business meetings while you closed million dollar deals.

Today we’re going to revisit the glory days of cocktails with one of classiest spirits of all: bourbon.

Old Fashioned

It’s not called an “Old Fashioned” for nothing. This tried and true cocktail has more class than an 18-year graduate student. There’s a reason that this was the drink of choice for Mad Men’s Don Draper.


  • 1 bar spoon of simple syrup
  • 2 dashes Angostura bitter
  • 2 ounces bourbon
  • 1 orange twist for garnish

Combine the simple syrup in a chilled rocks glass. Stir in the bourbon. Add ice. Enjoy with a twist of orange.

Whiskey Sour

The Whiskey Sour is another classically simple Bourbon drink. Some consider this the training wheels of whiskey, as the sour mix can cut the edge of the Bourbon, but a good Whiskey Sour will allow the flavors to mingle so that neither overpowers the other.


  • 2 ounces bourbon
  • ¾ ounce fresh lemon juice
  • ¾ ounce simple syrup
  • ½ orange wheel for garnish
  • Maraschino cherry for garnish

Simply mix the bourbon, lemon juice, and syrup in a cocktail shaker with ice and shake. Strain into a rocks glass with ice. Enjoy with the orange wheel and cherry.

If you’re looking to mix things up, you can try a New York Sour (notably enjoyed by the gentlemen of Boardwalk Empire) by adding ½ ounce of dry red wine. Make it a Boston Sour by mixing in an egg white.


If a Whiskey Sour is bourbon on training wheels, a Boulevardier is whatever motorcycle Meatloaf rode out of Hell. The Boulevardier mixes bourbon, Campari, and vermouth for a stiff, Negroni-esque drink that mingles and enhances the complex flavors of a good Bourbon. Try this with rye based, higher proof bourbon that can stand up to the Campari. Willet, Blanton’s, and Basil Hayden all have good options.

  • 5 oz. bourbon
  • 1 oz. Campari
  • 1 oz. sweet vermouth
  • Orange twist for garnish

Throw it all into a mixing glass with ice and stir. Serve in a chilled glass with an orange twist.

Mint Julep

Kentucky is known for a lot of things. Among the more reputable are Bourbon and horse-racing. This derby classic cocktail combines both. So maybe forgot the ridiculous hats and pastel dress clothes and ninety-degree racetrack. Just mix up one of these and catch the race on tv. Or maybe just skip the race altogether and watch a real sport.

This cocktail is best enjoyed with a 100 proof, barrel strength bourbon. Recommendations include Wild Turkey, Elijah Craig, and Four Roses.


  • 15 mint sprigs
  • 1 cup raw sugar
  • 3 fresh mint leaves
  • 1 1/2 ounces of 100 proof bourbon

First we have to make the mint simple syrup. To do this, toss the mint sprigs, sugar, and 1 cup of water in a medium saucepan over medium-high heat. Bring it to a boil then simmer for five minutes. Stir it occasionally. Sit back and relax for a minute until your simple syrup is room temperature then strain it and refrigerate for about half an hour.

Place the mint leaves in a julep cup. (The julep cup isn’t strictly necessary. I like to do all of my drinking out of a Garfield mug. If anything, this improves the experience.) Add 1/3 cup ice, then layer in 2 teaspoons of your mint simple syrup. Add another 1/3 cup ice on top then pour in your bourbon and stir. Finally add another 1/3 cup ice and pour in the remaining 1/2 oz. of bourbon. Top it off with 1 cup of ice, tightly packing into a dome. Garnish with mint leaves and insert a straw.


This citrusy cocktail was named for those who drank it during the prohibition. (Because they scoffed at the law.) It also sounds like a pretentious sneeze, which makes sense, as it was debuted in France.


  • 2 oz bourbon
  • 1 oz dry vermouth
  • 1⁄4 oz lemon juice
  • 1⁄2 oz grenadine
  • 2 dashes orange bitters

Add everything to a shaker with ice. Shake and serve in a chilled cocktail glass.

Whiskey Smash

This is another sweet cocktail that even the anti-whiskey crowd might enjoy. Convert your friends!


  • Half of a lemon, cut into wedges
  • 4 mint leaves
  • 3⁄4 oz simple syrup
  • 2 oz Elijah Craig 12-Year-Old Bourbon

First, muddle the lemon at the bottom of a shaker. Add the rest of the ingredients plus ice. Shake and then strain into a rocks glass with ice.

Bourbon Manhattan

A good Manhattan is the classic of classics. It’s easy to make, with just enough ingredients to either show off a good bourbon or bolster a bourbon that needs a little something.

While the Manhattan whiskey of choice is usually rye, using a sweeter vermouth (Noilly Prat Rouge comes to mind) makes for an equally smooth and satisfying drink.


  • 2 ounces bourbon
  • 1 tablespoon sweet vermouth
  • A dash of Angostura bitters
  • An orange twist and cherries to garnish

Pour bourbon, vermouth, and bitters in a cocktail shaker half full of crushed ice. Shake and serve in a chilled martini glass. Garnish with orange twist and cherries.

Bourbon and Beer Cocktails

Once you’ve gone through the classics, it’s always good to see what the kids are up to. These days the hip crowd is pouring beer into their cocktails. This unlikely marriage is a new classic in the making. As it turns out, nothing suits the sweetness of a bourbon like a nice, bitter IPA.

IPA Manhattan

This recipe, from the Pine Box Rock Shop in Brooklyn, New York, replaces the bitters in a typical Manhattan with an equally bitter and more alcoholic IPA.

Bell’s Two Hearted IPA is a good fit here, although anything particularly hoppy will do. For Bourbon, try Bulleit Rye Bourbon.


  • 2 oz bourbon
  • 1 oz sweet vermouth
  • 1 oz IPA
  • 1 brandied cherry

In a mixing glass, add two ounces of Bulleit Rye Bourbon, one ounce of sweet vermouth, and shake. Strain into your chilled martini glass and top with an ounce of your favorite bitter IPA. Garnish with a brandied cherry.

Bloody Hell Cocktail

This cocktail, created by thebeeroness.com, takes all the spicy joy of a Bloody Mary and adds the citrus of a blood orange and the cool fizz of an IPA.


  • 2 oz blood orange juice
  • 1 ½ oz bourbon
  • 1 tbs agave
  • 1 jalapeno, sliced
  • 2 oz IPA beer

In a shaker filled with ice, add the blood orange juice, bourbon, agave, and sliced jalapeno. Shake and strain into a highball glass with ice. Finally stir in your beer and enjoy.

The Southern 75

From the Proof and Provision bar in Atlanta, Georgia, comes a classically Southern way to enjoy Bourbon and Beer. The Boilermaker has nothing on this.

P&P uses Sweetwater IPA, but again, anything hoppy enough to balance out the bourbon will do.


  • 6 oz. India Pale Ale
  • 2 oz. bourbon
  • ¾ oz. fresh-squeezed lemon juice
  • ½ oz. demerara syrup (or simple syrup)

Pour the beer into a chilled collins glass. Pour the bourbon, lemon juice, demerara syrup into a cocktail shaker with ice, and shake. Strain the bourbon mixture into the beer and garnish with a lemon twist.

Dog Days of Summer

Unlike the other beer cocktails, this recipe opts for summer ale and depends on vermouth and cherry liqueur to balance the flavors of the bourbon. Crafted by Tristan Willey at New York City’s Long Island Bar, this cocktail is perfect for hot summer days.

  • 1/2 oz. Cherry Heering
  •  1/2 oz. Sweet Vermouth
  • 1/2 oz. Lemon Juice
  • 1/2 oz. Bourbon
  • 8 oz. of Sam Adams Summer Ale

Pour all ingredients over ice and serve.