Christen McClure is the Beverage Director at Nashville’s *Sinatra Bar*. (Photo courtesy of McClure)

“I just want someone to look at me the way Frank Sinatra looked at a glass of Jack Daniel’s,” laughed Christen McClure, who manages the beverage program at Sinatra Bar in Nashville, Tennessee. “I don’t think my own mom has ever looked at me that way!”

Sinatra was often seen sipping a glass of Jack Daniels on stage during sets, and there’s a photo in the restaurant of him focused on a glass of it, a look of jubilation on his face.

McClure’s list features a lineup of Jack Daniel’s, including the “3…2…1…Let’s Go!” serving Old No. 7 with three ice cubes and one splash of water, Sinatra’s preferred way of drinking the whiskey. The list is the only in the country to serve Jack Daniel’s Sinatra Century—a 100-proof Tennessee Whiskey created in 2015 for the hundredth anniversary of Sinatra’s birth—it goes for $250 an ounce.

I recently blind tasted several Jack Daniel’s whiskies with a panel in Los Angeles and followed up with McClure, asking her to create an original cocktail with one of our recommended spirits. She had noticed an uptick in the number of people ordering the espresso martini on her list—which she makes with Chambord Black Raspberry Cordial and calls “Lotta Coffee in Brazil.” She decided to create an iced coffee drink that people could easily make at home.

McClure chose Jack Daniel’s Bonded for its unique expression, while still remaining quintessentially Jack. “It has all of those classic banana, oat, honey and peanut shell flavors with a touch of salinity,” she says. “But the Bonded specifically has a lot more cinnamon, caramel and rich, developed sugar flavors. It’s three-quarters of the way to a cinnamon dolce latte.” She enhanced those flavors with a shot of espresso and maple syrup, served the drink over ice and topped it with a mixture of heavy whipping cream and Vespertino Tequila Crema, frothed with a milk mixer. While you can substitute Bailey’s or other cream liquors, McClure favors Vespertino—which tastes a lot like horchata—because it has a lifted cinnamon sweetness that matches the flavor profile of the cocktail. She calls the drink “Some Lucky Day,” which is a lyric from the Sinatra song, “Where Is the One.” It’s creamy and decadent. And it’s hard to have just one.

Ingredients

Some Lucky Day

By Christen McClure

1 1/2 ounces Jack Daniel's Bonded Tennessee Whiskey
2 ounces espresso
1 ounce real maple syrup
1 1/2 ounces Vespertino Tequila Crema
1 ounce heavy whipping cream
cinammon

Instructions

Brew 2 ounces of espresso or strong coffee. Rest it so it completely cools before mixing.
In a 12-ounce glass, mix the Jack Daniel’s Bonded and maple syrup with the cooled coffee. Add ice and a straw and give it a swirl.
In a separate glass, combine the Vespertino and heavy whipping cream and froth for 15-20 seconds, until the mixture thickens but doesn’t firm up. Pour the cold foam over the coffee mixture.
Garnish with a sprinkle of cinnamon.

Spirits Type:

Jack Daniel’s Bonded Tennessee Whiskey

ABV:

Distiller:

Jack Daniel Distillery, Lynchburg, Tennessee

Price:

$30

Jack Daniel’s Bonded Tennessee Whiskey
In 1897, the federal government first passed the Bottled-in-Bond Law that whiskey be made by a single distillery in one season, bottled at exactly 100 proof, then aged in a bonded warehouse. Today, whiskeys can consist of blends from multiple growing seasons or sourced from more than one distillery. Jack Daniel’s creates all their distillate in-house, but Old No. 7 is only 80 proof while a lot of the single barrel selections run at cask strength much higher than 100 proof. Their Bonded Whiskey is full of sweet caramel, cinnamon and coconut flavors. The body is pillowy soft, spiked with black pepper spice from a mash bill that includes eight percent rye. This is a great everyday whiskey that can play well with mixers.

Alissa Bica

Based in Los Angeles, California, Alissa Bica is the Associate Editor and Spirits Critic at Wine & Spirits. She is also a sommelier at 71 Above and co-runs the home wine tasting company, Côte Brune and Blonde. In any rare moments of free time, she writes about obscure grape varieties in the blog Off the Beaten Wine Path.