Billionaire Cocktail at Employees Only ($16)
Employees Only is a West Village classic, and for a good reason; while I've been to other old-guard cocktail bars recently that seem to be shadows of their former selves, EO impresses me every time. I'm more than happy to go with the bartender's choice, here, but if I'm ordering off the menu, it's often the Billionaire Cocktail: bourbon shaken with lemon, absinthe bitters, and the Employees Only grenadine, with notes of clove and cardamom.
Don't Forget the Flowers at Fedora ($13)
I'm a huge fan of Brian Bartels, who does the cocktail menus at all of Gabe Stulman's restaurants; he could've shown up on this list a few times. But Fedora is my favorite drinking place these days, and while I honestly can't point you to a single favorite on the list, I've recently been fond of "Don't Forget the Flowers": Milagro Blanco tequila shaken with lime and St. Germain, with grapefruit bitters and hum hibiscus liqueur. Complex, layered floral notes reined in by the tequila so that it doesn't get too, well, St. Germain-y. Love it.
Smoked Banana-Mezcal Margarita at Empellón Taqueria ($13)
Mat Resler knows his way around mezcal like few others in this city, and while his straight-up Fidencio Clasico margarita is worth an order, the Smoked Banana-Mezcal is even more remarkable. He caramelizes the fruit, purees it, smokes that puree, and uses it as the base of a margarita, also using Fidencio Clasico, "with its smoky, earthy, citrus notes." Chef Alex Stupak has gotten a great deal of (well-deserved!) recognition for the work he's done at both Empellóns, but don't forget about the bar program.
Presbyterian's Revenge at Highlands ($13)
Highlands is billed as a Scotch bar (and definitely known as a drinking bar; weekend nights get rowdy)—but don't overlook former bar director John McCarthy's cocktail list, whether or not Scotch is your spirit of choice. (While McCarthy's moved on from Highlands and Whitehall, the cocktail menu at Highlands hasn't changed.) I've had an impressive number of Presbyterians in my day, and never seem to tire of them: Black Grouse with the distinctive bitter bite of Cynar, shaken with lemon and grapefruit bitters to lighten things up, with a big twist of grapefruit on top. Much more refreshing and drinkable than most Scotch drinks I know.
Royal Bamboo from The Spotted Pig ($13)
I'm a sucker for a good sherry drink, and loved this Royal Bamboo at the Spotted Pig: La Gitana Sherry, Dolin Blanc Vermouth, and Angostura with a cava float. (It's also one of the lighter ones on this list, which, when you're at your third or fourth stop on a cocktail crawl, is very much appreciated.)
Bank Robber at The Marrow ($12)
I don't necessarily think of Harold Dieterle's other two restaurants, Kin Shop or Perilla, as places I'd stop in for a cocktail (I'd be too busy stuffing my face with goat curry). But I'd swing by The Marrow for a Bank Robber, a take on the Boulevardier: a Negroni-style drink with Punt e Mes and Campari, with Bulleit bourbon rather than gin.
Mata Hari at Orient Express ($13)
More than once, I've intended to get drinks at the Spotted Pig only to find a line out the door and a bar crowd I didn't want to fight through. My new solution? Walk right down the block to Orient Express. I loved the Mata Hari, the union of bourbon, mezcal, and lemon with a subtle bite of ginger.
Camo-Carlita at Anfora ($13)
I've long known Anfora as an excellent, comfortable wine bar, where I walk out knowing more about Riesling or Lebanese Cabernet than when I went in. But until recently, I didn't realize they were a great place for cocktails, too. Here's the "Camo-Carlita": Sauza tequila shaken with chamomile syrup, lemon, lime, and grapefruit, and topped with Lambrusco Rosso. (Champagne and prosecco are old news; I've started seeing more Lambrusco cocktails around the city. I'm a fan.)
The Crippler at The Tippler ($14)
Okay, it's not quite in the West Village, but 1. The Tippler is just a short wander from spots like Anfora and The Marrow; and 2. I love it. (Plus the Meatpacking is really just an extension of the West Village, and if you're in the Meatpacking and want cocktails your best bet is probably the Tippler.)
Okay, enough location-justifying, Tippler's cocktails justify themselves. It's hard to make a drinkable, balanced high-proof cocktail, but The Crippler comes off as very polished, with initial gentle butterscotch-vanilla rum notes (J.M Overproof Rhum and the Austrian rum-tea liqueur Stroh Jägertee) before the bite of WhistlePig rye and Vida mezcal come in, and it tingles all the way down.
Casino at Little Branch ($13)
Little Branch's cocktail menu is about as classic as they come, good for those who love a well-made Old Fashioned or Last Word. On a recent visit, I had a lovely Casino (gin, Maraschino, lemon, orange bitters), but often find myself ordering Bartender's Choice. Never been unhappy with the various stirred bourbon drinks that's gotten me.
Yes, it's an exterior shot. It's dark in there, guys.