There are few symbols in the drink world more powerful, more recognizable or more American than the Martini glass. An angular monument to Deco design, its characteristic V-shaped bowl and fine stem have long represented that most iconic of drinks, so much so that there is arguably no other image that better communicates the very notion of the cocktail.

There is also no glass more despised by today’s bartenders.

“It’s a problematic glass,” says Greg Boehm, founder of Cocktail Kingdom, which supplies some of today’s most popular bar tools, from bitters dashers to artisan syrups to, notably, glassware. “It’s incredibly impractical.”

Veteran bartender Toby Cecchini puts it even more bluntly: “Those glasses are odious. They’re horrible. They spill everything. They’re just miserable.”

But impracticality isn’t solely to blame for the glass falling out of favor; it’s equally a matter of what the Martini glass has come to represent. Today it is less Deco icon and more neon symbol of the cocktail’s dark ages—a glass overflowing with several decades of negative association, and Pucker.

To understand how that came to be, it’s important to consider how, and when, the glass became synonymous with the drink in the first place. Though it made its formal debut at the 1925 Paris Exhibition (by many accounts, as a modernist take on the coupe), it didn’t catch on immediately. And when it did, it wasn’t necessarily used for cocktails; as David Wondrich points out in Imbibe!, the glass as it appears in the films of the 1920s is depicted as being used much like the coupe—for Champagne.

Meanwhile, the Martini, as a drink, was growing swiftly in popularity. Having been invented in the mid-19th century, it was bolstered in the 20th by Prohibition, which had crowned gin as the country’s preferred spirit. Not only had the speakeasies of the era fashioned the drink into something both stylish and urbane, they had ushered in a new age of drinking, writes Max Rudin in “There’s Something About a Martini,” his deep-dive essay on the subject published in American Heritage in 1997.

“Outlawing liquor,” he explains, “had put the gentlemen-only saloon and hotel bar out of business,” and replaced it with “a new cocktail culture where women drank with men.” It would ultimately prompt a drinking-buddy camaraderie between the sexes, epitomized by characters like Nick and Nora Charles, the Martini-drinking crime solvers in the 1934 novel and film, The Thin Man. It also laid the groundwork for the rise of the cocktail party, a cultural institution that would become a fixture of American life for the next several decades.

Bringing the cocktail out of the bar and into the home had a twofold effect on the Martini as we know it today: Not only did the process of making the drink become ritualized (“In the 1930s, mixing cocktails at home became one of the manly arts, like carving a turkey,” writes Rudin), the approach to serving it did, too, as it spurred a new market for home barware. Sampling from the same modernist aesthetics that had similarly shaped the era’s architecture, interiors and furnishings, more geometric examples of glassware were suddenly in high demand.

“The symbolism of the drink and the new cultural perception of this particular glass shape come together in the 1940s,” explains Lowell Edmunds, author of Martini: Straight Up, “[because] it became culturally possible to see that particular glass design as au courant.” It was in that decade, too, that the glass first became known, at least colloquially, as the “Martini” glass, its outline, according to Rudin, “one of the few American designs to make a seamless transition from moderne to modern.” Before long, it had become so ubiquitous—and the drink so popular—that in 1958, a New York Times article would describe it as “the symbol of our civilization.”

But it was during that era, too, that the iconic drink would begin to change.

“[J]ust as architecture moved in the direction of brutalism, so the Martini became excessively dry, flavorless vodka replaced gin, and the ritual of mixing was abandoned in favor of the Martini on the rocks,” writes Edmunds. “In both cases, the esthetic impulse of modernism was carried to a self-defeating extreme.”

What had once been, in effect, an emblem of the middle-class cocktail party was by the ‘60s being outwardly shunned as disagreeably dry, too spirituous and representative—both literally and metaphorically—of American corporate values as epitomized by the advertising culture of Madison Avenue.

“The purity, transparency, and lack of messiness of the perfect American cocktail now seemed to mirror a sterile lack of messiness in life and work,” explains Rudin, “won at the expense of emotional involvement and the realities of life.”

Following its nearly two decade-long decline, the Martini would fall out of vogue entirely by the early ‘70s. In 1973, Esquire derided it as “a bitter, medicinal-tasting beverage” that represented “everything from phony bourgeois values and social snobbery to jaded alcoholism and latent masochism.” By 1976, it earned a notable, albeit damning, mention in American politics when, in a debate with Gerald Ford, Jimmy Carter famously suggested that the working class was subsidizing the “$50 Martini lunch,” solidifying the drink’s reputation as an unfortunate emblem of conservative America.

Still, however, the Martini glass remained fixed in the country’s imagination, consequently lending its glass—not to mention its name—to many of the oversized, fruit-infused vodka drinks of the 1980s and ‘90s.

That word “Martini,” before long, had become so overused that in a story written in 1998 by William Grimes for the New York Times Dining section, the Martini was described as having entered its “late-Elvis” phase, with Grimes lamenting the drink’s modern permutations and suggesting that a “modern Dante, if so inclined, could tour the many circles of this cocktail hell and come up with a truly compelling mixed-drink Inferno.”

Though today’s craft cocktail movement has helped the classic Gin Martini shed these decades-old associations, the glass remains, for many, one of the last remaining pillars of the Technicolor “‘tini” craze that gripped the country prior to the drink’s revival. Add to that the fact that today’s bartenders have famously looked beyond Prohibition to the age of Jerry Thomas—in which coupes were considered the vessel of choice for such a drink—and it’s no surprise that the Martini glass has been effectively usurped in favor of rounded, even more classic stemware. Ironically, that same element of symbolism that first propelled the Martini glass to fame is exactly the thing that’s lead to its ultimate demonization within the craft market.

Which begs the question: Is the Martini glass—admittedly still a prominent fixture in many parts of the country—primed to fall by the wayside? Or will it come back around? After all, there are plenty of more practical vessels whose burdens figure far less into the American bartender’s imagination.

But, then again, when conjuring up an image of a cocktail—neon sign, or otherwise—does anyone really think of a coupe?