Jack Daniel's Gentleman Jack Recipe

Measure and combine

Add 2 oz Gentleman Jack, 1 oz sweet vermouth, 2 dashes orange bitters, 1 dash Angostura bitters and 0.25 oz simple syrup (if you prefer a slightly sweeter, silkier drink) into a mixing glass.

Add ice and stir

Fill the mixing glass with plenty of ice. Stir gently with a bar spoon for 20–30 seconds (about 20–30 full turns) until the liquid is well chilled and properly diluted — the mixing glass should feel cold to the touch and slightly frosted.

Prepare glass

Place a large ice cube in a chilled rocks glass. If you prefer no dilution, use one large clear ice cube; otherwise use fresh cubed ice.

Strain

Using a strainer, pour the chilled mixture over the large ice cube in the rocks glass.

Express orange peel

Take an orange peel about 1.5–2 inches long. Hold it over the glass and quickly bend or fold it skin-side down to express the citrus oils over the surface of the drink, then run the peel around the rim and drop it into the glass.

Add cherry (optional)

If using, place a Luxardo or brandied cherry on a pick and rest it on the rim or drop it into the drink for aroma and a touch of sweetness.

Serve immediately. Sip slowly to appreciate the smooth, charcoal-mellowed Gentleman Jack balanced with sweet vermouth and bitters.

If you don't have a mixing glass, build the cocktail directly in the chilled rocks glass and stir with a bar spoon against the inside of the glass. Use a strainer or hold back ice with the spoon when pouring if necessary.