Gentleman Jack from Jack Daniel’s Tennessee Whiskey is the more sophisticated older brother of the distillery, packed with flavor but a little more on the subdued side. It’s double mellowed for extra smoothness, which provides a lot of obvious benefits but means creating cocktails is a bit harder—you wouldn’t want to waste Gentleman Jack’s excellent flavor on a cocktail that doesn’t highlight it. These four cocktails have their own unique flavor, but each makes sure that Gentleman Jack shines through.

Gentleman and Ginger

Lets start with something simple yet bold. The Gentleman and Ginger has only a few ingredients: Gentleman Jack, ginger beer or ale, and a squeeze of lime. These ingredients are common enough in a cocktail—and for good reason. The ginger and whiskey combine for a wonderful palate that manages to be both assertive and mellow, and the lime heightens the flavors of both.

Ingredients
35ml Gentleman Jack
75ml Ginger Beer/Ale
Squeeze of Lime
Cubed Ice

Method
Build all the ingredients in a glass over ice, stir and garnish with a slice of lime

Gentleman’s Manhattan

This is a new take on an old classic. Sweet Vermouth and Dry Vermouth mixed together make this cocktail strong and keeps the flavor profile relatively simple while adding variety. Gentleman Jack provides the base, and with 2 dashes of bitters and a fruity garnish there’s a new experience waiting in every sip.

Ingredients
50ml Gentleman Jack
15ml Sweet Vermouth
15ml Dry Vermouth
2 Dashes of bitters

Method
Shake and strain into a chilled cocktail glass. Garnish with a cherry or lemon twist.

Whiskey Sling

Another old classic, this time on the more refreshing side. The whiskey sling can be very simple—just add some lemon juice and simple syrup to whiskey and you have a strong but sweet and refreshing cocktail that’s excellent for sipping at any time or occasion. Gentleman Jack ups the game with its signature smoothness, increasing the drinkability, and with the extra room a few dashes of orange bitters comes in to keep things citrusy and refreshingly interesting.

Ingredients
4 Parts Gentleman Jack
1 Part Lemon Juice
1 ½ Part Simple Syrup
2 Dashes orange bitters

Method
Shake all ingredients with ice. Then strain into an ice-filled glass. Garnish with a lemon.

Mellow Espresso

This one goes out to all the coffee drinkers out there, and everyone who wants to know what the after dinner drinks life is about. The mellow espresso combines whiskey, vanilla sugar syrup, espresso, and coffee cream liqueur. It’s great for sipping long into the night, and a perfect balance of sweet and bitter, just like Gentleman Jack.

Ingredients
35 ml Gentleman Jack
12 ml Vanilla Sugar Syrup
35ml Espresso
35 ml Coffee Cream Liqueur

Method
Pour all ingredients into a cocktail shaker, shake and pour into a glass.