Right in the heart of the Flatiron District, this swanky cocktail joint evokes the bygone days of the Jazz Era—and has one of the most extensive bar menus around, too. You can almost see Frank Sinatra propped up in the corner of the Art Deco-style room, sipping his gentleman’s drink (that’s Jack Daniel’s with a splash of water). All ingredients are freshly muddled, minced, and made to order; the drink menu changes with the seasons. Try a martini if you lean toward the classics or dive into a specialty cocktail, like the Devil Went Down to Georgia (bourbon, lemon, peach, and Tabasco) or the aptly named Dying Bastard (gin, Cognac, bourbon, housemade lime cordial, ginger, and Angostura bitters). If you’ve got the whole evening ahead of you, go one step further and order the cocktail flight of the day so you can sample a little bit of everything.
