Let’s chat about one of the all-time classic cocktails – the Jack Rose. No, not Jack and Rose from Titanic – Jack Rose, the cocktail. Never heard of it? You’re not alone. The Jack Rose has quietly survived for more than a century and has almost single-handedly kept applejack alive in the cocktail world. It’s bright, crisp, and refreshing, with just enough tartness and sweetness to make it perfect for early autumn. If you’re expecting something heavy like an Old Fashioned or Manhattan, think again. The Jack Rose is lighter, fruit-forward, and incredibly easy to enjoy.

Not familiar with applejack either? Then that’s the best place to start. Applejack is a type of apple brandy that dates back to the American colonial era and is considered one of America’s original distilled spirits. Its name comes from the way it was traditionally produced: freeze-distilling, or “jacking,” hard apple cider or apple wine. Because it was relatively easy to make, applejack experienced a resurgence during Prohibition before declining once Prohibition ended. While applejack appears in several classic cocktails, none is more closely associated with it than the Jack Rose.

As with many classic cocktails, the true origin of the Jack Rose, and even its name, remains something of a mystery. One popular story claims it was named after mobster Jacob Rosenzweig, better known as Baldy Jack Rose, who supposedly enjoyed an Applejack Sour with a splash of grenadine. The problem with this theory is that the cocktail was already well known before Baldy Jack Rose rose to prominence.

A more likely origin points to Frank Haas, a veteran bartender at Eberlin’s on Wall Street in New York City. In 1899, a newspaper reporter wrote about sharing a Jack Rose with Haas at Eberlin’s, one of the earliest documented references to the drink. If Frank Haas sounds familiar, it may be because he’s also credited with creating the Daisy cocktail, which I’ve written about before.

By 1948, David A. Embury included the Jack Rose among the cocktails every bartender should know in The Fine Art of Mixing Cocktails. It was also mentioned in Ernest Hemingway’s The Sun Also Rises and was reportedly a favorite of John Steinbeck. Despite its place in cocktail history, the once-popular Jack Rose has largely been overlooked during today’s craft cocktail revival. I think it deserves another try this fall.

With a simple three-ingredient cocktail like the Jack Rose, having the best-quality ingredients is a must, so be sure to use fresh lemon juice and make your own homemade grenadine (I promise, you’ll thank me once you taste it).

Jack Rose

– 2 ounces applejack or apple brandy
– 3/4 ounce fresh-squeezed lemon juice
– 1/2 ounce homemade grenadine

Combine the applejack, lemon juice, grenadine, and ice in a cocktail shaker. Shake well and strain into a chilled cocktail glass. For an extra touch of seasonal flair, rim the glass with cinnamon sugar before preparing the drink.

Simple Homemade Grenadine

Combine two parts pomegranate juice with one part sugar. While you can heat the pomegranate juice, it can quickly become bitter, so I prefer to leave it at room temperature and whisk in the sugar until it is fully dissolved. Add a splash of orange blossom water and mix well. Once all the ingredients are well blended, refrigerate the grenadine until ready to use.

Sometimes the best cocktails aren’t the newest ones – they’re the classics just waiting to be rediscovered. With apple season in full swing, there’s no better time to pour yourself a Jack Rose and discover why it has stood the test of time. Cheers!