“I’ll have a Martini.” Four little words; infinite paths. Gin or vodka? Up or on the rocks? Dirty? Filthy? Wet? Damp? Dry or dry, as in, just show me the vermouth bottle? With a twist? An olive? An onion? A dash of orange bitters?

To the seasoned Martini lover, this exchange presents an opportune moment to flex their carefully whittled preferences. To the uninitiated who grew up in the era of Martini equals cold shaken vodka, or worse, cloying Appletini, calling up a bespoke Martini build is almost as confusing as it is intimidating. It’s no wonder it took me two decades to determine that I indeed have a Very Specific Martini order: It’s a 50:50, but I’ll get to that later.

I’m a ’90s kid; my dad was a salesman whose windfall came in the heady late ‘90s and early aughts, so we started going out to posh dinners at birthdays and Christmastime.

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“Dry vodka Martini with an olive!” Dad proclaimed with bravado when the waiter arrived. The cocktail was gorgeous in its conical glass; clear and viscous with a few thin ice shards floating on the surface above a fat green olive — fit for the sculpturally suited type who casually drops “mergers and acquisitions” into every conversation. Once or twice Dad slid the glass over so I could try a sip.

“Now that’s getting your money’s worth,” he said, eyeing my pinched-face reaction. From then on, I was convinced that a Martini was nothing more than a cold glass of booze — its drinker’s sole reprieve a few speared olive snacks.

The ’90s ’Tini

“I started bartending in the 1990s, and I don’t think I even saw a bottle of vermouth for the first few years,” recalls Eric “ET” Tecosky, the former longtime bar manager of Jones Hollywood in Los Angeles who also founded Dirty Sue Premium Olive Juice. “I worked in a lot of clubs, and if we did make an actual Martini, it was probably just shaken vodka.”

This was the heyday of Martini bars; Tecosky worked for a time at an L.A. bar called the Martini Lounge — with nary an actual Martini on the menu. There, “Martini” was a catch-all for the technicolor lineup of sugary, vodka-based concoctions served in a triangular glass, like Appletinis, French Martinis, Lemon Drops, and “Sex and the City”-nodding Cosmos. Places that did serve the classic usually made it with improperly stored vermouth.

“It got away from itself for a decade or so, but the Martini is one of the originals. When you order one, it just feels classier; it echoes of a different time.”

On a brand trip to San Francisco in 2006, where the craft cocktail revolution was already under way, everything changed for Tecosky, then bar manager at Jones. The Bay Area bartenders talked about cocktails differently; they frothed drinks with egg whites and made bitters in house.

“I had been bartending at this point for probably 15 years, and what they were talking about was foreign to me, so I kept my mouth shut,” Tecosky says. Like the bar and fine-dining scene of my early 2000s Chicago, the cocktail renaissance hadn’t yet reached L.A.

Within a week, Jones transitioned to all fresh juices. Tecosky bought Dale Degroff’s seminal 2002 book, “The Craft of the Cocktail,” and re-trained himself and his staff on the classics: Old Fashioneds, fresh Margaritas and, yes, Martinis with (fridge-stored) dry vermouth.

“It got away from itself for a decade or so, but the Martini is one of the originals,” Tecosky says. “When you order one, it just feels classier; it echoes of a different time.”

History repeating

The Martini had indeed been there all along — in print since Harry Johnson published a Martini cocktail in his 1888 “Bartender’s Manual,” comprising equal parts Old Tom gin and vermouth, a few dashes each of gum syrup and bitters, and a dash of curaçao or absinthe “if required.” It originated sometime and some way before. Whether you believe Martini di Arma di Taggia invented it at the Knickerbocker Hotel in New York, that it owes its name to vermouth brand Martini & Rossi, or that it evolved from the Martinez — which itself possibly began in a California bar of the same name during the Gold Rush — is your affair.

Revisiting Degroff’s history of the Martini in The Craft of the Cocktail,” we can roughly pinpoint how we reached the era of “hold an open bottle of vermouth in front of a fan across the room,” as Degroff cheekily wrote. From the early 1:1 days to Post-Prohibition, “America got wetter” and the quality of available gins improved, so “the Martini got drier,” Degroff wrote. (Not long after, President Franklin D. Roosevelt supposedly popularized the Dirty Martini.) Following the Second World War, gin was still king, but the vermouth portion diminished dramatically — as the horror of war supercharged folks’ need for a stiff drink. “By 1960, the Martini was a lethal 11 parts gin to 1 part vermouth,” Degroff wrote. The Cold War era made the Martini stronger still — and gave us the Vodkatini, as clever placement by Smirnoff helped vodka surpass gin as the white spirit of choice at the time.

“There’s something very nostalgic about the Martini, and I think that’s why it’s having this renaissance right now.”

Fast forward through the Wall Street flexing and ’tini crazed ‘90s and cocktail revolution-fueled 2010s, and American cocktail culture has matured. Martinis are trending again, their age-old riffs (Vesper) and sacrilegious mixing methods (shaken not stirred) buoyed in part by the pop culture baggage of James Bond’s protracted return to theaters. Bartenders aiming for differentiation in a crowded market — or perhaps just having fun — are reviving Martini riffs like the Alaska and Dean Martin’s go-to Flame of Love (vodka and fino sherry) or conjuring Martinis flavored like Giardiniera and Caprese salads.

The ’90s are back in full swing, too: fanny packs, balloon jeans, and Carrie Bradshaw on the small screen; meanwhile, upmarket iterations of the French Martini (featuring house blackberry liquor) and Dirty Peacock (the headline on the menu at newcomer Madeline’s Martini in the East Village). Playful adaptations at Madeline’s — all oversized — also include the Bikini Martini (vodka, coconut rum), Martini By The Sea (mezcal, sea lettuce brine, and bianco vermouth), and a forthcoming Sour Apple Martini (gin, fresh-pressed green apple and cucumber, Midori-honey syrup, and lemon juice.)

“There’s something very nostalgic about the Martini, and I think that’s why it’s having this renaissance right now,” says Madeline’s co-owner Pete Canny. “Everything goes full circle and comes back into popularity; I mean, look how popular Carbone is. I wanted to hate it — I don’t want to pay $95 for chicken Parm my grandfather could make better. Then I went for the first time, and I was like, I get it. That’s how things are going in the Martini world right now.”

For me, this proliferation of bespoke Martinis and derivatives merely represents more options for a cocktail I already find fraught with too much choice. But it’s high time I tried it again.

What should a ‘Martini’ taste like?

“Gin Martini?” I ventured at a bar recently, the self-doubt evident in how my intonation inadvertently formed a question. Then came the onslaught of follow-up questions. I blurted out “Dirty!” to make them stop, knowing full well I’d be stuck getting sloshed on a glass of gin seasoned with old olive juice. A few weeks later, I had better luck with a 50:50 Martini at a steakhouse, though I balked when asked for my gin preference: “Oh, whatever the bartender thinks,” I said.

“Where it gets super tricky for me is if I go into a bar, even, like, a reputable cocktail bar, I can’t be like, ‘I want X-to-X-ratio Martini.’”

Exasperated, I paid a visit to Danny Shapiro at gin-based cocktail bar Scofflaw in Chicago’s Logan Square. Shapiro self-describes as more of a traditionalist, who was mentored by dogmatist Paul McGee and built his bartending foundation on books like “The Fine Art of Mixing Drinks” by David Embury.

“All you need is foundational knowledge of very few cocktails to build out entire menus,” Shapiro tells me. I relaxed a little; already the Martini felt more accessible. I explained a few likes and neuroses: that I don’t want to get drunk off of one cocktail and enjoy a 50:50, that I like all kinds of gin, but I also don’t really like making decisions or seeming high-maintenance in bars. Shapiro started me on a 50:50 Martini with Old Tom gin and Dolin dry vermouth. It was, as he aptly put it, “light, floral, citrusy, friendly,” but also, explicitly, not a Martini the way I thought it should be.

Then I requested Scofflaw’s house gin Martini, which means 2 and a quarter ounces of Brokers dry gin, three-quarter ounce of Dolin dry vermouth, and a dash of house orange bitters, stirred for a solid minute — “a lot Martinis are understirred,” Shapiro says. He set a tiny coin of lemon peel afloat on the drink in its etched Nick & Nora glass. As I sipped it, I delighted in the bite from the slightly heavier hand of gin (but far short of Dad’s boozy specs). The cocktail was clean, elegant and fragrant with citrus; I felt fancier even perched next to it.

Could this be my Very Specific Martini order?

No, but it’s certainly the aperitif I’ll order every time I come to this bar. Therein lies the challenge, Shapiro says, because we simply don’t know what we’re getting from one bar to the next.

“Where it gets super tricky for me is if I go into a bar, even, like, a reputable cocktail bar, I can’t be like, ‘I want X-to-X-ratio Martini,’” Shapiro says. “You might be able to say a gin preference; but you’re certainly not giving a dry vermouth or orange bitters preference without being the most high-maintenance drinker. I’d rather go to a place, try the Martini, see if I like it. If I don’t, I’m never drinking that Martini again.”

That said, his failsafe order is a 50:50 on the rocks. It’s a lower-alcohol aperitif that’s hard to screw up. Even if the bartender understirs, the ice will slowly dilute it. Plus, “it’s the one ratio controller you can do without sounding like a total dickhead,” he says.

Tecosky rightly points out that bartenders are in the business of making drinkers happy, even if we drinkers are real pieces of work. “If someone is a Martini drinker they’re going to tell me, ‘This is how I like Martinis.’ And I’d rather have that than have me guess and they send it back.”

Yet Shapiro and I came to realize that a Martini order isn’t just what we like; it’s a compilation of our generational and cultural baggage, our situation on a particular day, and the type of patron we are or want to be seen as. I discern that perhaps I’m more of an occasional Martini drinker because part of what makes me happy is showing up at a bar or posh restaurant and drinking something that’s already been calibrated to perfection by someone else.

Though when in doubt, I’ll make it a 50:50 on the rocks, ordered with plenty of attitude.