Five Rebellious Old Fashioned Cocktails to Try
Five Rebellious Old Fashioned Cocktails to Try

The Old Fashioned cocktail is more than just a drink—it’s a legacy. Steeped in history and tradition, it has stood the test of time to remain a staple in the world of cocktails. Originating in the early 19th century, it was simply referred to as a cocktail and made of sugar, bitters, water, and whiskey.

Over the years, it has seen many variations, but its essence has remained untouched, proving its enduring appeal among cocktail enthusiasts and bourbon lovers alike.

Here are five Rebellious old-fashioned cocktails you have to try.

Kentucky straight bourbon whiskey is at the heart of any old-fashioned. Many make the mistake of choosing a whiskey that’s weak or that they simply want to “get rid of” when making a cocktail. However, due to the simplicity of an old-fashioned, this is a huge mistake.

With a cocktail like this, you must choose a bourbon you love. Maybe don’t choose the most expensive bottle you have on the shelf, but pick something you appreciate every time you take a sip.

Enter Rebel 100, a bourbon that commands attention with its bold, rich flavor profile and smooth finish. This 100-proof whiskey strikes the perfect balance, offering depth and complexity without overwhelming the drink’s nuanced flavors. Its versatility makes Rebel 100 ideal for giving classic cocktails a distinct edge.

Classic Old Fashioned Recipe

Sometimes, there’s a bit of confusion with the classic old-fashioned – usually in the form of muddling fruit. Let’s set the record straight: there is no muddled fruit in a classic old-fashioned.


  • 2 oz Rebel 100 Bourbon
  • 1 sugar cube
  • 2-3 dashes of Angostura bitters
  • Orange twist (for garnish)


  1. Place the sugar cube in an Old Fashioned glass and saturate it with the bitters.
  2. Muddle until the sugar is dissolved.
  3. Fill the glass with large ice cubes, add the Rebel 100 Bourbon, and gently stir.
  4. Express the oil of an orange peel over the glass, then drop it in.
  5. Indulge in the classic Old Fashioned with a twist that only Rebel 100 can bring—rich, nuanced, and utterly satisfying.

Smoky Maple Old Fashioned

Pairing the robust notes of Rebel 100 Bourbon with the sweetness of maple syrup and the enigmatic allure of smoked wood results in a comforting and invigorating cocktail.


  • 2 oz Rebel 100 Bourbon
  • 1/2 oz pure maple syrup
  • 2 dashes of Angostura bitters
  • A small piece of smoked wood or smoked salt (for garnish)


  1. In an Old Fashioned glass, combine the maple syrup and bitters.
  2. Add Rebel 100 Bourbon and fill the glass with ice.
  3. Stir until well chilled.
  4. Garnish by smoking the cocktail with a smoking gun or by adding a pinch of smoked salt.

This Smoky Maple Old Fashioned is a nod to autumnal nights by the fire. It blends sweetness, smoke, and the unmistakable kick of Rebel Bourbon.

Spiced Orange Old Fashioned

A seasonal take incorporating the zestiness of orange and the warmth of spices creates a cocktail that envelopes you like a cozy blanket.


  • 2 oz Rebel 100 Straight Rye Whiskey
  • A dash of orange bitters
  • 1 sugar cube
  • A sprinkle of ground clove and cinnamon
  • Orange twist (for garnish)


  1. In an Old Fashioned glass, muddle the sugar cube and bitters.
  2. Add a sprinkle of ground clove and cinnamon.
  3. Fill the glass with ice, add Rebel 100 Straight Rye Whiskey, and stir well.
  4. Garnish with an orange twist.

The Spiced Orange Old Fashioned evokes the essence of the holiday season, making every sip a celebration. The rye adds that extra oomph that’s always been missing in your life.

Blackberry Sage Old Fashioned

Combining the tartness of blackberries and the earthiness of sage, this variant offers a fruity and herbal dimension to the traditional cocktail.


  • 2 oz Rebel 100 Bourbon
  • 3 fresh blackberries
  • A few sage leaves
  • 1 sugar cube
  • 2 dashes of Angostura bitters


  1. In an Old Fashioned glass, muddle the blackberries, sage leaves, sugar cubes, and bitters.
  2. Fill the glass with ice and pour in the Rebel 100 Bourbon.
  3. Stir gently until the cocktail is chilled and the flavors are well combined.
  4. Garnish with a sage leaf and a blackberry.

Sip on the Blackberry Sage Old Fashioned to enjoy a tantalizing mix of refreshing and intricate flavors.

Barrel-Aged Old Fashioned

This sophisticated variant involves a bit more preparation but results in a cocktail that’s rich, smooth, and worth the wait.


  1. Combine 750ml of Rebel 100 Bourbon, 24 oz of simple syrup, and 1 ounce of Angostura bitters in a barrel.
  2. Seal the barrel and age for 2 to 4 weeks. Don’t do longer than that or the drink could break down and turn bitter.
  3. To serve, pour the aged cocktail through a strainer (to catch any barrel residue) into an Old Fashioned glass filled with ice and stir gently.
  4. Garnish with an orange twist.
  5. Add more sugar or bitters as needed.

The Barrel-Aged Old Fashioned takes the classic to the next level, offering layers of flavor that unfold with each sip.


The Old Fashioned cocktail is a testament to the timelessness of good taste. By exploring these five unique variations—each highlighting the unparalleled qualities of Rebel 100 Bourbon and Rebel 100 Straight Rye Whiskey—you’re not just preparing drinks but crafting experiences.

Stock up on Rebel Bourbon by finding a retailer near you.