Perhaps by virtue of its inextricable link to the Brandy Alexander, crème de cacao has managed to earn a distinctly sweet and ultimately not-so-serious reputation.

“The first time I encountered crème de cacao, it was not being used properly,” says Seth Freidus, formerly of Boston’s Alden & Harlow. “It was seen in drinks with sweet on sweet on sweet on vodka.”

It wasn’t always this way. Invented in France, crème de cacao was likely first created in the late 16th century, when monasteries began distilling seed and nut liqueurs. Drunk neat throughout the 1800s, it didn’t begin appearing as a mixer in drinks until the turn of the century—most famously shaken with equal parts gin and cream in the Alexander, a precursor to the Brandy Alexander, which rose to fame a few decades later.

A heavy-handed drink, the sweet, creamy cocktail garnered popularity during Prohibition, as it could easily mask the taste of the era’s “bathtub gin.” But that’s not to say it was particularly well-received. In 1934, a year after Prohibition was repealed, newly founded men’s magazine Esquire released a list of the 10 worst drinks of the past decade—among them, the Alexander. 

One notable exception came a few years later in 1937, when British bartender William J. Tarling developed the Twentieth Century cocktail for the Café Royal in London. Named for the world-famous Twentieth Century Limited rail line, which ran between New York and Chicago, the drink skips cream altogether, balancing crème de cacao with gin, Lillet Blanc and lemon juice, a move that modern bartenders agree is still a good way to use the liqueur. (The 19th Century, a riff on the drink from the now-closed Pegu Club, swaps the gin for bourbon, while Joaquín Simó’s take, the Colonial Affair, leads with cacao spirit.)

“Crème de cacao definitely has a kitsch factor, which can be good in small doses,” says Henry Prendergast, a longtime Chicago bartender. In New York, in fact, Eamon Rockey reimagines the kitschy Chocolate Martini as a streamlined digestif. On the other end of the flavor spectrum, a small amount of crème de cacao can bring balance to acidic or bitter cocktails. Just a splash of the liqueur figures into the Negroni Absinthe, for example, a mezcal Negroni riff featuring a sherry-based vermouth that also imparts its chocolate notes to the drink, while the Scorpion Kick, a Daiquiri variation, adds an unexpected dose of crème de cacao to the rum classic.

There are two main types of crème de cacao, white and dark. In the Grasshopper from Tujague’s in New Orleans, both versions, along with both green and white crème de menthe, come together for well-rounded, layered flavor.

While both types of the liqueur are chocolate-flavored, dark crème de cacao often gets its signature hue from caramel coloring, which some bartenders find to have an artificial taste. But others have found success with the deeply dark chocolatey version produced by Tempus Fugit, which does not use any additives. Punch contributor Al Culliton uses the liqueur in the Michaelmas Term, where it harmonizes with rye, port and Averna for a quintessentially autumnal drink. And at Canon in Seattle, Jamie Boudreau’s Chocolate Salty Bols combines Bols genever, crème de cacao, rum and Earl Grey–infused vanilla hemp milk. “The maltiness of the Bols marries perfectly with the cacao, and the vanilla hemp milk rounds everything out,” he explains. Finished with bitters, a spoonful of boba and a pinch of sea salt, it’s a modern, playful retort to the creamy cacao cocktails first shaken up a century ago.