ON AN OPERATING TABLE, his mind anesthetized blank, his rib cage butterflied, his harvested arteries set atop a stainless steel tray like ghastly hors d’oeuvres, my father not long ago had quadruple bypass surgery. He was sixty years old. The night before the operation, he and my mother went to a restaurant in downtown Cleveland (he was a patient at the Cleveland Clinic), where he dined lightly on steamed mussels and linguini. He indulged in two glasses of Valpolicella table wine and, after supper, a few sips of a snifter of Cognac. This represented a deviation from custom. As he was paying his check he cadged from the waitress a cigarette, of a make and a model—white from filter to tip, possibly Menthol, possibly Ultra—no doubt less fulfilling than his traditional Marlboro Red. Fifteen days prior he had quit smoking, forty-eight years after taking his first drag—two packs a day, essentially, ever since. The smoke he snuck (my mother, in the loo at the time, would never have let this occur) was a small indulgence, a last nod to a decadent past perhaps no longer to be tasted. But in no way did it satisfactorily replace the two most important items of a post-supper ritual he first developed as a twenty-five-year-old insurance salesman in Erie, Pennsylvania. In no particular order those items were (a) a cigar, if possible a Montecristo, and (b) a stinger on the rocks. It is unclear which was the more significant. “If I couldn’t have a cigar,” my father said recently, recalling that last supper in Cleveland, “then I wasn’t going to have a stinger.”

I’m certain that most of you have never even heard of the stinger, and you should not feel ashamed. An obscure after-dinner drink, eighty years past the prime of its popularity, it is enjoyed now, when enjoyed at all, not really as a digestive but almost as a kind of liquor dessert. As such, the stinger is sometimes not even considered a “cocktail,” which implies a libation to be consumed in quantity during pre-sit-down hours set aside for affected, if well-oiled, conversation. But a cocktail it certainly is, and, like all classic cocktails, the stinger has its singular pleasures. The martini, for example, piercing and astringent, is primarily consumed at bars after work, at parties made up of the insufferable, at ill-timed wedding receptions during frantic summer holiday weekends; that is, the martini serves to burn the anxiety of adult life quickly and decisively from the lower spinal cord. The stinger, however, decadent and ameliorative, is preferably sipped following a meal of sizable dimension—large and fine enough to cause a person to feel satisfied beyond want yet desirous nonetheless of one thing more. The stinger is thus consumed to prolong and heighten that experience, to keep those fine times gunning along, to delay the inevitable anticlimax of getting into the cab and heading home to bed. The medicine of the stinger doesn’t kill the germ; it prevents it.

According to the best cocktail-recipe books of today, a stinger is built of three parts brandy to one part white crème de menthe. Shake, strain, pour over crushed ice into a brandy, cocktail or old-fashioned glass. Golden brown, distinguished in appearance, a well-made stinger looks, somehow, like liquid marzipan. Sip, however, and you will not detect the faint essence of almond, but a quivering of mint over the cask-wood wine-depth of brandy. Some bartenders, and some volumes of drink recipes, including the 1971 Playboy’s Host & Bar Book, counsel an equal ratio of ingredients. But this inevitably results in a drink that tastes, as the uninitiated often complain, like mouthwash. Recently, at the bar of the Drake Hotel in Chicago, the barkeep, a fellow in his mid-fifties with a large capillary-burst nose, passed over a stinger proportioned equally between brandy and menthe. Straightaway I could tell, from its weak Lipton’s shade, that he’d produced a sickly sweet confection, its value as a dental hygienic somewhat in question. I asked for a little help. He drained some Korbel into my glass, burnishing the drink like wood stain.

David Wondrich, former professor of English literature at St. John’s University, cocktail autodidact, Esquire magazine’s resident drinks expert and self-proclaimed stinger hobbyist, says, “It’s strange. You wouldn’t think so, but stingers are easy to screw up in bars.” When overly menthed, the drink to a discerning palate can seem “disgusting, syrupy.” To avoid this, some professionals have come to prefer ratios of as much as four-to-one brandy. Gary Regan, British-born bartender and author of The Joy of Mixology, likes his stingers with three ounces of brandy plus a quarter- to a half-ounce of white crème de menthe—a dry stinger indeed. “And I like to use a dryish cognac like Hennessy,” he adds. “If you make it that way, you know you’re having a real drink. Meanwhile, the white crème de menthe makes it refreshing.” Perhaps a bit of the iconoclast, Wondrich prefers Armagnac, which, he says, has “more of a funkiness to it . . . it fights against the medicinal tendencies of the crème de menthe.” He describes a correctly made stinger in this way: “The clean, fresh taste of the mint rises above the mellow roundness of the cognac without obscuring it. A very dangerous drink, though.”

Dangerous, indeed. Many nights have I made stingers for myself and a few friends, looked down at my watch sometime later and discovered that it was five in the morning. One stinger can easily turn into more than one and, on occasion, as many as six, in which case it is important not to take the next day too seriously. Something about the drink fords the paths of conversation. My father and his companions were infamous for following the stinger along this uncertain course. Cause and effect: gin rummy matches, a dollar a point, until sunrise; unspeakable weekends in places like the Bahamas. Epic times have been related to me in which these men would mix stingers by the pitcher. I am filled with envy and terror. In restaurants, chairs up on all the other tables, waiters powerless and impatient and hovering in corners to await the end of the tab, it often became important for my father to stoke the smithy of his words with a glass of pure brandy, which he measured as necessary into his waning stinger. I’ve seen him do this a hundred times, irritating whole unions of food-service personnel.

Younger men at the time, in their thirties and forties, my father and his friends had yet to experience their heart troubles or their joint ailments or their cancers of the varying organs. Some have since died. Others just eased up. One of my father’s friends, his business partner for thirty years, recently said, “Nothing good has ever come of a stinger.” I believe he was only half joking. He used to order his stingers (a little flamboyantly, I think) with a dash of Angostura bitters. Now sixty years old, an avid buyer of wine, he has since sworn off the cocktail completely, unsure of his ability to keep it to just one or, failing that, his ability to deal with the consequences of failing that. “It’s a young person’s drink,” he explained. As of this essay’s printing, my father has not had a stinger since October 4, 2003, four days before his quadruple bypass surgery. He does not know precisely when he will drink one again. “Probably a couple of weeks,” he said the other day, at home in the midst of his uneven recovery. “I don’t have any cigars here, either. I’ve got to stop and order some.” He said this somewhat noncommittally. We were talking over the telephone. There was a pause. He apologized and suggested we carry on the conversation a little later. “I just took a painkiller,” he said. “Let’s wait until that kicks in.”

For late-night stinger episodes to occur outside your own home, you need to hit upscale restaurants, possibly a hotel bar. I must warn you, though, that the stinger has fallen to its nadir, hardly a surprising development given the state of the culture. Rarely does even a so-called professional know what it is, and many bars do not stock one or both of the ingredients. As my father has said, “They almost have to know you’re coming.” Neither neighborhood taverns nor sports bars, of course, will do. Even supposedly urbane drinking places—hipster lounges and fashionable nightclubs—will have a hard time summoning stingers. Following dinner at Mia Francesca, a popular and quite good Italian restaurant on the North Side of Chicago, a friend and I tried four different bars—including the restaurant’s—attempting to order a stinger. Looks of bewilderment met our requests. One bartender even consulted a cocktail guide. She flipped to the S section and read for a few moments. “Huh,” she said, apparently edified. She tossed the book back on the shelf and poured us two vodka gimlets, a drink (lime juice, vodka) that seemed to me at that moment as vulgar as afternoon television.

At the final establishment, an unlikely sounding place called the Nisei Lounge, our bartender nodded and returned with two highball glasses filled with a nauseous murk the color of puddles on the lot of a gasoline distribution facility following a period of heavy rain. He apologized. The bar, he said, stocked only green crème de menthe. Green crème de menthe, though identical in flavor to its transparent sibling (the only additive is food coloring), induces in the drinker some kind of synesthesia, resulting in a stinger that tastes like a cross between baby aspirin and a fluoride treatment. But we thanked the bartender for his trouble and sipped our stingers just the same. We live lives of compromise, after all, and when the stinger fix is in—or any fix, for that matter—a person has a way of surrendering aesthetics before anything else. Under no circumstances, in other words, do you turn away the murk. “When you’re in dire straits,” my father says with the force of parable, “you use the green crème de menthe.”

Recent scholarship has determined that the modern stinger was likely invented sometime in the first or second decade of the twentieth century, thus debunking the myth that the drink, with its refined palate-cleansing quality, originated during Prohibition to remedy the taste of bathtub hooch—a myth that has become attached to many other cocktails as well. “People were just worried about getting some whiskey down their throats. They didn’t have a lot of time to be messing around mixing up cocktails,” says Gary Regan, in a voice so deep and slurry one has the sense that his account of Prohibition constitutes a primary source. Perhaps the first reference to a stinger in a widely available cocktail-recipe book came in 1914, with the publication of Rawling’s Book of Mixed Drinks, by Ernest Rawling, a San Francisco bartender, and Drinks, by Jacques Straub, “formerly wine steward at the Blackstone, Chicago, and the Pendennis Club, Louisville,” according to the volume’s author bio. Tom Bullock’s The Ideal Bartender, published in 1917, perhaps the classic of the genre, has a recipe for “Stinger, Country Club Style.” Bullock tended bar at the St. Louis Country Club, among other establishments, and apprenticed under the man who invented the julep. Bullock’s stinger calls for “1 jigger Old Brandy” and “1 pony white Crème de Menthe,” a bit sweet, but approaching the modern formulation. A predecessor drink, known as the Judge, was being consumed in the late nineteenth century, according to a recipe that appears in an 1892 volume called The Flowing Bowl, by one William Schmidt. A hyper-sweet version of the stinger, the Judge contained brandy, crème de menthe and simple syrup, with the liqueur, astonishingly, outweighing the brandy.

Just when the simple syrup was removed, and by whom, and the resulting cocktail named a stinger, no one knows. Nor do we know the reason for the nomenclature. Other concoctions have, over the centuries, been referred to as “stingers,” an appropriate enough name for anything alcoholic. British colonialists in nineteenth-century Malaya, for instance, used the term for Scotch and soda. And in 1913, the New York Times reported that the Bustanoby brothers—New York restaurateurs, owners of the famous Café de Beaux Arts and, as such, inventors of the nightclub—had just opened their newest innovation, a “ladies’ bar,” where they were serving something called a “stinger,” whose main ingredient was Amer Picon, a Campari-like liqueur.

But, thankfully, the appellation stuck to none of these other cocktails, and by the time Prohibition arrived, the stinger as we now know it had reached the height of its esteem, due mostly to the libationary predilections of one man. In 1920s Manhattan, Reginald Vanderbilt, grandson of Cornelius, scion of the fortune, among the era’s most notable bon vivants, drank stingers not just after dinner, but any chance he got. He sucked them down, visibly, ostentatiously, in large amounts, at the Colony, his favorite restaurant and speakeasy, the Jazz Age equivalent of Studio 54. Among the Vanderbilt set—smart and not like you or me—his taste quickly became the fashion. One can envision people in sumptuously tailored clothes on the roofs of Manhattan speakeasies; in their hands rock glasses that flash golden brown and, inside them, ice pieces glow like jewels.

In the 1930s, the ultra-exclusive Nassau Gun Club of Princeton, New Jersey, put out a cocktail guide that contained just ten recipes, the members’ favorite drinks and, therefore, the only drinks worthy of their erudite attention. The stinger, of course, was among them. To this day an aristocratic air persists in the nose of the cocktail.

The stinger remained relatively popular all the way up until the 1970s, when the whole of American cocktail culture, at the hands of the then-young baby boomer generation, plunged into the bottled-water, jogging-regime abyss, casting into obscurity and nostalgia many fine cocktail institutions, not the least of which was the lunch of the three martinis. My father, born two years prior to V-Day and perhaps a little behind his own times, had his first stinger in 1968, while dining with a Philadelphia executive of the Travelers Insurance Company, in town to recruit my father for the firm. Following dinner, the executive, a rather sophisticated fellow of forty or so, with a modish suit and a dashing mustache, an echo in his carriage and in his taste of Vanderbilt at the Colony, offered my father a cigar and suggested that he accompany his smoke with a stinger on the rocks. “I had both,” my father says. “And I’ve been having them ever since.”

From probably the age of ten I was my father’s stinger maker. This was, by far, my most important chore. Almost every weekend a meal of proper dimensions would be prepared at our house. Filet of beef, rack of lamb, perhaps a cutlet or chop of veal—these were the most common entrées. And, of course, following the meal, I would be instructed to prepare a stinger. So accustomed did we get to the routine that over the years my father stopped even saying the words “stinger” and “son.” From across the dinner table, plates cleared of food, napkins sprawled on the tabletop, his wineglass empty, his legs crossed and his coffee on the way, his eyes would meet mine and flash wickedly. Despite this fixed pattern, almost always his silent request would come to me as an annoying surprise. Why is he looking at me like that? And then a sigh of recognition, a glance at the ceiling, and up wordlessly, begrudgingly, from my comfortable spot at the table, over to noodle about in the liquor cabinet, and off with my bottles to prepare the kitchen counter for my work. (This feeling persisted only until I came of age and starting making pairs of stingers instead of one at a time.)

The experts recommend cognac from Cognac and crème de menthe from at least somewhere in France—Marie Brizzard and Get 27 are generally considered the best brands. Inexpensive crème de menthe, poorly made, is evidently too sweet. My father, on the other hand, had a pragmatic mind. Of working-class stock, he cut the recherché elitism of the stinger with a bracing dash of frugality. “I find that the cheaper the brandy the better the stinger, except for a little splash of the good stuff,” he says. And the crème de menthe? “The cheapest you can buy.” His rationale is based on the notion that, for stingers, the white ingredient serves the same function as garnish. Thus my father’s cabinet almost always contained the American brandy E&J and a plastic bottle of some near-nameless crème de menthe, the kind that has on its label a big green cartoon mint leaf, marijuana-like. In recent years, though, as he indicated, my father has taken to dribbling on top of his stingers a layer of Courvoisier, of Hennessy, of something with a cork in it.

I don’t recall my first lesson in stinger mixology, but I do know that I worried a lot about screwing up the proportions. My father wanted them dry, two-and-a-half parts brandy to one-half white crème de menthe. For the first few attempts, my naive mind equated cocktail balance with one-to-one ratios, and I’d have to bring my father the brandy bottle so he could repair the damage. But it wasn’t exactly French pastry cooking, so it didn’t take me long to master the craft. Also, lacking the proper bar tools, we never shook our stingers, just stirred them right in the glass. Fill three-quarters full with brandy, float the menthe on top. Stir gently—bingo, perfect.

The key, too, was to taste your own work, a little nip before serving, so as to sense firsthand when you had it right and when you had it wrong—the scientific method. My first draft of stinger caused that familiar neck-shiver. I thought I’d sipped an alien ipecac, and wondered about the wisdom of growing up at all. But soon I became accustomed to the flavors, began even to like them, and soon I began to enjoy very much the process, the craft, of stinger construction. Among my father’s friends, who occasionally came over to our cottage in upstate New York for a day and a night and a difficult morning, I became rather famous for my dry, carefully built stingers. Tending bar, always a seat of power, I had a boy’s pride in creation, in celebrity, in the novelty of a twelve-year-old mixing drinks. It was a kid’s thrilling glimpse into the life of adults, a kid’s chance to participate in the fringes of that life and, in a sense, to facilitate it. With stingers in mid-make, I stood only a few steps away from the dream of manhood. A few minutes or hours later, with stingers in mid-drink, as I listened in on the resulting conversation and laughed at jokes I did not understand, my longing only increased.

Out of all that stinger talk, drips of wisdom fell my way, directly and indirectly, from lecture and from eavesdrop. Late one night, at one of his favorite restaurants, the place empty and our dinner complete, my father sat across from me. We were man and boy. I was thirteen years old. The waitress, who knew the routine and did not require instructions, placed beside my father a coffee and a stinger on the rocks. After she had disappeared, he took a sip from his glass, then a long draw from his cigar, which he had clamped between fingers that seemed to me gigantic. He exhaled slowly, pointing the smoke toward the ceiling. His eyes were far away and at ease with the world. I sensed philosophy on his lips. “Son,” he began smoothly but gravely, his legs crossed and his body addressed to me at an angle that in my imagination now suggests an old ward healer about to divulge his secrets. “Do you know what a blow job is?”

There proceeded a long and discursive discourse on sex in which most of my private confusions and humiliations were laid to rest, made to seem as natural as the wind. And so inevitably the thirteen-year-old moved on, entered high school, entered college and, sooner than that, began to get the jokes, just as my palate had gotten the stinger.

In making my father’s stingers, the most difficult task by far was the first step in the process, the preparation of the ice, about which he was quite particular. Most stinger recipes recommend crushed ice as opposed to cubed for those who want them on the rocks. (The stinger is sometimes, though rarely, served straight up, as it typically was pre-Prohibition, in which case it comes now as it came then, in a martini glass.) My father, however, demanded cracked ice, which bars in modern times hardly ever offer, for the ice must be cracked by hand. This causes pain. Depending on how many stingers have been ordered, frostbite becomes a concern. In the palm of your hand place a cube—although if a refrigerator produces it, it’s less a cube than a crescent moon—and grasp in your other hand a soupspoon, the larger the better. With the curved back of the spoon, take aim. Thwack! Thwack properly and the cube will explode compactly in your hand, a geology of schist and powder. Thwack improperly and you must thwack again, escalating the hurt, your palm as pink as a Swede in a sauna. If you fear pain, and do not cup your hand enough, ice pieces will shower about the kitchen, off walls, onto the floor, over the countertops, landing and pooling. It can get messy. My mother, mostly struggling alone to contain the pans, pots, plates of the post-dinner situation, would be driven nearly insane by my stinger making. I felt guilt.

It took me years (I’m not lying) to reach the point of ice-crack mastery; I can now splinter enough for two stingers—using around fifteen cubes per drink—in about a minute flat. To crack ice with any efficiency or aplomb, you must first master a certain wrist action, floppy, whipping, like a bunker shot. This is best achieved by holding the spoon’s handle loosely between thumb and forefinger. Thwack. It is impossible to reproduce the sound of spoon metal striking ice and causing it to explode, but as I moved through boyhood the cracking of cubes each stinger evening at our house and the tinkling of their debris as it hit the glass bottom became to me a kind of music. It meant that it wasn’t bedtime yet.

This piece orginally appeared in the January 2004 issue of Maisonneuve.