The Dessert-y Cocktail with a Bad Rap (& Why It’s Unfair)

In honor of where we came from (that is, our mothers), we're exploring the origins of some of our favorite foods and drinks. Today: the Brandy Alexander.

In the ever-raging battle between cake people and #teampie, I’m a noted sweet tooth Switzerland—I prefer to drink my dessert. After any given meal, I’m far more likely to spring for a nip of good whiskey or a glass of golden Monbazillac than to come to blows over baked goods.

When I’m craving something that’s a little more along the lines of brownie-in-a-glass, though, I always turn to the Brandy Alexander. A grandmother to the (somewhat maligned) chocolate martini, the Brandy Alexander is a smooth, rich libation consisting of one part brandy (or Cognac), one part Crème de Cacao, and—just to up the milky ante—one part cream. Shave a little bit of nutmeg on top, and yes, it is every bit as luxurious as it sounds.

It’s also a libation that occupies a strange place on the space-time continuum of cocktails, and has often felt to me like a drink without a proper historical home.

The Brandy Alexander’s ancestral drink is the Alexander, which was crafted with gin—not brandy—as the base spirit. According to historian Barry Popkin, the first iteration of the drink was likely made by (and named after) bartender Troy Alexander, who is said to have invented it at the Rector Hotel in New York shortly after the turn of the century. (The Rector was a go-to spot for whooping it up in its day, but sadly shuttered in 1914.)

Tasked with the project of creating an all-white drink to celebrate the fictional, all-white-wearing railroad advertising character Phoebe Snow (not to be confused with the bluesy-voiced 70s singer of the same name), Alexander tossed a bunch of beige-hued liquors together in a glass and the first Alexander was born. It also explains, to some degree, why the cocktail has been so readily pegged as a “lady drink” from the start: It was actually invented to honor a woman (even if she wasn’t, you know, real).

This history, though, is wobbly at best. Popkin also notes that a 1915 edition of the Philadelphia Inquirer claims the drink was invented to celebrate pitcher Grover Cleveland Alexander during a particularly contentious World Series with the Red Sox.

Then, there’s a fleet of other Alexanders, all of whom—at some point or another—are said to have inspired the cocktail. Noted Algonquin Round Table lush and drama critic Alexander Woollcott liked to claim he was its namesake. (He also liked to greet his friends by saying, “Hello, Repulsive!”) One rumor still circulating is that the drink was named in honor of Russian Tsar Alexander II, which makes little linear sense. But almost every Alex of the day, it seems, tried to get in on the action.

After being committed to print in Hugo Ensslin's 1916 work Recipes for Mixed Drinks, the cocktail took off in the U.S. during Prohibition, and abroad when it was the featured creation at the wedding of Princess Mary in 1922. Also around this time, enterprising drinkers began swapping out gin for other spirits—including brandy. (A version featuring egg white even found its way into S.C. Arthur’s cannon classic, Famous New Orleans Drinks and How to Mix ‘Em.) While the exact moment when the Alexander’s gin-based tipped into brandy territory isn’t quite known, by the 1930s, the transformation was all but complete, and the Brandy Alexander was a hit.

In our current cocktail renaissance, the drink’s modern position is a bit baffling. No one really knows where to place it, and it’s rarely seen on menus. It’s a little too milkshake-like to nestle up against its spirit-forward pre-Prohibition brethren, but looks like an old blue-hair beside latter-day concoctions. Kitschy-fun drinks like the Grasshopper and Tom Collins have found a new lease on life at places like Long Island Bar and Pepe le Moko, but somehow the Brandy Alexander hasn’t seen the same swell of enthusiasm. Instead, it has become a pop culture touchstone that few people actually ever really drink.

The stereotype it so often carries, though, might just be why no one is sounding the alarm for its revival. Likely due to its inherent sweetness, the Brandy Alexander is painted in film, books, and music as the drink of naiveté and—ninety percent of the time—that means a young woman is sipping it. We’ve come a long way in whacking gender norms from our cocktails and spirits, but the Brandy Alexander is still presented ad nauseum as a real Eve-before-the-apple drink.

Nowhere is this more prominent than in the 1962 film The Days of Wine and Roses, where the Brandy Alexander serves as the movie’s primary, disastrous catalyst. In the opening scenes, Jack Lemmon’s character—a burgeoning alcoholic—convinces a wide-eyed, chocolate-loving teetotaler (played by Lee Remick) to try one. From a single Brandy Alexander, Remick’s drinking habit quickly spirals like a Reefer Madness nightmare, and she sinks into life-ruining, alcohol-fueled despair.

While decidedly less dramatic, later decades reinforced a similar notion of the drink as one for inexperienced female drinkers. The patron saint of hat-tossing single women everywhere, Mary Richards, goofily orders a Brandy Alexander during her job interview on the pilot episode of the Mary Tyler Moore Show (commence laugh track). Even Feist’s 2007 song, “Brandy Alexander” somehow sounds breathlessly girlish when she lilts, “He's my Brandy Alexander, always gets me into trouble, but that's another matter, Brandy Alexander.”

Then there’s Peggy Olson, who asks for a Brandy Alexander on a bad blind date in season one of Mad Men when she’s a jittery, fledgling secretary-copywriter. By the show’s penultimate episode? She’s a confident badass swigging scotch with her boss and rollerskating through an abandoned office. The juxtaposition couldn’t be stronger.

Since the Brandy Alexander is a drink with a history that’s largely anyone’s guess, it feels only fair to pay a bit more attention to how we begin building its future. Maybe this year, we shake off the Brandy Alexander’s pigeonholed identity—tinker with it, gussy it up, gulp it down—in an effort to show just how versatile it can be: boozy enough to run with other brown liquor bad boys, but playful enough to inspire some tongue-in-cheek interpretations.

And maybe, just maybe, someday we’ll see a fearless heroine on the silver screen order one before heading off to fight crime or save a busload full of children.

Hey, a girl can dream.

How do chocolate martinis—and Brandy Alexanders—make you feel? What other cocktails seem to have unfair reputations? Share your thoughts in the comments below!