What’s the Ultimate Steakhouse Dinner Cocktail?

Few doctors will recommend eating steak for dinner five times in a single week. No doctor will recommend washing said steaks down with three—four—six—eight stiff alcoholic beverages each night.

But science requires sacrifice.

No, I’m no hero, folks—just a man who took it upon himself to solve a problem that has plagued mankind for literally fives of years. Namely: which cocktail goes best with a steak dinner.

See, as a cocktail lover in a steakhouse town (New York City), I’m often wracked with doubt when deciding which blended, stirred or shaken concoction to order with a beef-based meal. As I know there are others with the same problem, I convinced five friends of mine to accompany me to five different Manhattan steakhouses to determine the ultimate cocktail for pairing with steak. Classics, modern twists and experimental inventions were all fair game―so long as the liquid contender was high in alcohol and had the potential to taste wonderful alongside a Flintstones-sized slab of charbroiled cow.

This was my journey—kidneys and liver be damned.

When I walk into Strip House and see the dimmed lights, romantic red wallpaper, and sexy red leather booths, I quickly realize I might have made a mistake in passing over my wife in favor of Food & Wine writer Mike Pomranz as my guest. Mike quickly proves himself a worthy date, however, even before our server arrives, by describing his vision of the ideal pairing. To his mind, a beverage must either complement, contrast or conceptually relate to the food on the plate.

I ask him, given that system, which cocktail would he pair with steak.

"That's what we're going to find out tonight," he sagely replies.

I miss my wife again.

Richard Breitkreutz, corporate beverage director for BR Guest Hospitality (owners of Strip House), and Michael Vignola, corporate executive chef for the restaurant, admit that they sell more wine than mixed drinks here. But Breitkreutz has some cocktail tricks up his sleeve, too. After a few appetizers, he introduces us to a Barrel-Aged Old Fashioned that pairs beautifully with Vignola's coffee-crusted short rib. The rye cocktail is barrel aged in-house for at least six weeks, mellowing the drink and imparting it with tannins.

Mike nearly loses his mind, declaring, "Favorite drink. Favorite course. Favorite pairing." The intensity of the coffee rub plays well with the whiskey flavors, while the harshness of the rye overrides the soft texture of the sous-vide short rib. "It's everything I want," Mike says.

For me, the combination is a bit too intense. However, when Richard offers us a Pineapple Scotch Whisky Sour to go with our steak and eggs dish, I lose my mind over the conceptual pairing that nods to breakfast (subbing pineapple for orange juice). The drink is also refreshing, light and fruity enough to contrast the meat, while the smokiness and salinity of the 2001 Glenrothes (and its ground black pepper garnish) complements the dish.

I’m not yet sure what we accomplished today, but I do know that it was delicious. And that Mike “That's what we're going to find out tonight” Pomranz is a grifter who will say anything for a steak dinner.

Rule No. 1: Listen to restaurant staff suggestions.

Following a classic steakhouse experience, I decide to visit a more modernist establishment with my friend Lawrence Weibman, a TV producer and director known as "The NYC Food Guy." Less than a year old, the menu at Quality Eats is full of creative food mashups that appeal to a younger crowd more attuned to artisanal values.

Pushing for a non-whiskey cocktail, I ask for a Bloody Mary. Bar Director Bryan Schneider reluctantly puts one in front of us, warning that the savory-meets-savory pairing won't work as well as I think it will. He’s right, of course (see Rule No. 1). As great as the Bloody is on its own, the pairing is like dousing the exquisitely cooked hangar steak with ketchup.

Schneider tells us he’s taking charge of our next cocktail and wows us with a Cracker Jack Old Fashioned —made with Rittenhouse rye infused with crackerjacks and peanuts, Peychaud bitters and a "disappointing toy prize" (mine was a pair of Groucho glasses). This gem pairs perfectly with their Don Ameche filet mignon, served atop chicken liver mousse and caramelized onions. "Caramel meets caramel," Lawrence guiltily declares of the incestuous pairing. The Cracker Jack works wonderfully with the sugary char of this steak, but this is, after all, a very particular piece of beef. The drink’s sweetness wouldn’t work for all meat.

Our perspective shifts again when we try a cocktail called Cura, inspired by a Brazilian Caipirinha "cure-all" recipe. Schneider infuses Yaguara cachaça with black garlic, then adds honey and lime for a savory drink that goes magnificently with short rib. Here, Lawrence and I realize that, by comparison, the Cracker Jack Old Fashioned is an assault on the senses. While the Cracker Jack is the most titillating cocktail we tried, the balanced Cura is the one that goes the distance.

Referring to our quixotic quest, Schneider says, "I predict you'll come back to a Gin Martini," explaining that the crisp, refreshing classic cleanses and resets the palate for each bite of steak.

I excuse myself so I can go home and take my cholesterol medication.

Rule No. 2: Balance is paramount.

By day three, I feel like my pulmonary system would be completely clogged with fat if it were not for the lubricating solvency of alcohol. I estimate I’m operating at 50 percent. Thankfully, my visit to the New York Yankees Steakhouse―a modern, kitschy house of sports worship―gives me a jolt of much needed adrenaline. Especially because I’m joined by Pamela Wiznitzer, president of the New York chapter of the United States Bartenders' Guild and creative director at Seamstress NY, one of the best bars in the country.

But when, in light of my closing conversation with Schneider last night, I suggest a dry Gin Martini for my steak, both Pam and Head Bartender Chris McGuire tut-tut me, explaining that gin botanicals will only get in the way of the meat's flavors. That cocktail, they explain, is best saved for seafood such as shellfish or crudo. At this point, I’m just doing whatever the last person I spoke with said I should.

McGuire tells me that he prefers aged spirits when he’s eating steak, and whips up a fantastic Manhattan made with Michter's bourbon, Carpano Antica sweet vermouth and Angostura bitters. It goes incredibly well with our 18-ounce bone-in NY strip. Pam usually prefers rye (the spicier, more traditional choice) in her Manhattans, but she happens to love the choice of Michter's, calling the drink "perfect."

Yet, before I can drop the balloons and shout, "mission accomplished," Pam has to go and complicate things, pointing out that a large piece of the pairing equation is about ritual. For example, saké might not objectively go better with sushi than a dry Champagne or crisp pilsner, but at a Japanese restaurant, it's part of the culinary culture. In other words, context is everything. This place is built around American fun, entertainment, and nostalgia—so naturally, we order Yankeetinis.

This shockingly blue beverage consists of Absolut vodka, white cranberry juice and blue curaçao, served up in a martini glass. It’s sweet and insipid, and we sip it alongside a 27-ounce cowboy cut ribeye, a deliciously fatty piece of meat on a bone in which the chef has actually carved my first name. The pairing is on par with cotton candy and tuna salad, but I’m having the best time I've had all year.

"Drinking is supposed to be fun," Pam reminds me.

Rule No. 3: Sometimes, fun trumps nuance.

Capitalizing on this theme of "fun" (a point my colon might disagree on), I next head to STK, a trendy steakhouse / modern lounge that's all about "vibe dining." When I settle into my table with Emily Wells, writer and founder of cocktail blog Gastronomista, a DJ is scratching over Justin Bieber's "Love Yourself." (Appropriate, because―as my new diet proves―I don't.)

The food is the true star at this bar-centered, party-loving restaurant. Chef Andy Kitko's juicy porterhouse steak is truly impressive. Having already been dissuaded from pairing meat with gin, I try the beef with a dirty Vodka Martini, which consists of Tito's vodka, olive brine and a blue-cheese-stuffed olive. To me, this modern, vermouth-less take on a Martini should be reclassified as a "Vodka Olive,” but Emily argues that this preparation allows one to taste the true quality of a spirit. I do enjoy the cocktail on its own, but when paired with the meat, the salt-on-brine proves too much for my mouth.

No matter. STK proceeds to hit it out of the park by pairing their signature Not Your Daddy's Manhattan with Kitko's sublime ribeye. This bourbon-based cocktail is nearly identical to the one we had last night, except traditional bitters are subbed for Fernet-Branca, the Italian amaro. It’s delightful with the cooked meat.

Thus far I'm finding that whiskey pairs most consistently with steak. But there are only so many times one can assault one’s tastebuds with the charred flavors of Manhattans, Old Fashioneds and steak without growing weary. No problem, says Emily. "Have a Martini to get the party started, and do your whiskey cocktail with the steak."

Now we’re getting somewhere.

Rule No. 4: Don’t be afraid to shake things up, mid-meal.

You know when something sounds like a good idea in theory…but actually only causes stomach cramps and meat sweats? That's how I feel going into Day 5 of nothing but steak and cocktails for dinner. Maybe Don Draper could handle this much animal fat and alcohol in a week, but the show never revealed how long he lived after teaching the world to sing.

As a New Yorker, I'm comforted as I walk into Wolfgang's, one of the city’s most traditional steakhouses. The brand now has 13 restaurants worldwide, including one with a fantastic beverage program in Beverly Hills, but their original Park Avenue location is old school. Owner Wolfgang Zwiener worked for 40 years as head waiter at Peter Luger, arguably the greatest―certainly one of the oldest―steakhouses in the country. Growing up on Long Island, I have fond memories of going to Luger's for special occasions as a kid. Wolfgang’s makes me feel like I’m home.

My guest for the finale is good friend Alex Moore, vice president of content at SpinMedia, who muses, "It feels like Sinatra ate here," as he looks up at the vaulted, subway-tiled ceilings. Coincidentally, our waiter, Dino, looks like a Yugoslavian version of a younger Ol' Blue Eyes. "Don't forget my name," he whispers to me with a thick accent as he points to my notepad. (I wouldn't dare, Dino.)

Basking in tradition, I order three classic steakhouse staples: shrimp cocktail, Caesar salad (anchovies, a must) and a dry Beefeater Martini with olives and a twist. Next: a porterhouse for two, creamed spinach, German potatoes and onion rings. "It tastes like when you used to be able to smoke in restaurants," Alex says of the meal.

Yet, when Dino asks me what I'd like to drink with my main course, I can't pull the trigger on the rye Old Fashioned I'd planned on ordering. Call it habit; call it fate. (Or call it snapping after four days of drinking liquor.) But a bottle of Amarone della Valpolicella beckons, and I can't resist. And let me tell you, the relationship between astringent tannins and rich fat; the mingling of smoky-sweet barrel notes and char of the meat; the rush as I gulp the red liquid thirstily and gnaw on bone like Game of Thrones royalty—it's all fantastic.

An hour later, as we're stuffing in the last bite of cheesecake and whipped cream "schlag" we can muster, Alex notes, "Well, that was aggressive for a Tuesday."

Tell it to my cardiologist, Alex.

Rule No. 5: The best steak cocktail is the one you aren't spoiled with every day.